A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design

Journal of Medicinal Chemistry

Volumn 58, Issue 11, 2015, Pages 4383-4438

  Beno, Brett R ^a   Yeung, Kap Sun ^a   Bartberger, Michael D ^b   Pennington, Lewis D ^b   Meanwell, Nicholas A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROTEIN; SULFUR;

CHEMICAL INTERACTION; DRUG DESIGN; HYDROGEN BOND; MEDICINAL CHEMISTRY; MOLECULE; REVIEW; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METABOLISM;

DRUG DESIGN; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; PROTEINS; SULFUR;

EID: 84929384579     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501853m     Document Type: Review

References (342)

1. Nicolaou, K. C.; Chen, J. S.; Dalby, S. M. From nature to the laboratory and into the clinic Bioorg. Med. Chem. 2009, 17, 2290 - 2303
2. Prinsep, M. R. Sulfur-containing natural products from marine invertebrates Stud. Nat. Prod. Chem. 2003, 28, 617 - 751
3. Parry, R. J. Biosynthesis of some sulfur-containing natural products investigations of the mechanism of carbon-sulfur bond formation Tetrahedron 1983, 39, 1215 - 1238
4. Aoki, H.; Okuhara, M. Natural β-lactam antibiotics Annu. Rev. Microbiol. 1980, 34, 159 - 181
5. Basak, A.; Mandal, S.; Bag, S. S. Chelation-controlled Bergman cyclization: synthesis and reactivity of enediynyl ligands Chem. Rev. 2003, 103, 4077 - 4094
6. Shen, B.; Hindra; Yan, X.; Huang, T.; Ge, H.; Yang, D.; Teng, Q.; Rudolf, J. D.; Lohman, J. R. Enediynes: exploration of microbial genomics to discover new anticancer drug leads Bioorg. Med. Chem. Lett. 2015, 25, 9 - 15
7. VanderMolen, K. M.; McCulloch, W.; Pearce, C. J.; Oberlies, N. H. Romidepsin (istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma J. Antibiot. 2011, 64, 525 - 531
8. Bertino, E. M.; Otterson, G. A. Romidepsin: a novel histone deacetylase inhibitor for cancer Expert Opin. Invest. Drugs 2011, 20, 1151 - 1158
9. Borthwick, A. D. 2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products Chem. Rev. 2012, 112, 3641 - 3716
10. Feyen, F.; Cachoux, F.; Gertsch, J.; Wartmann, M.; Altmann, K. H. Epothilones as lead structures for the synthesis-based discovery of new chemotypes for microtubule stabilization Acc. Chem. Res. 2008, 41, 21 - 31
11. Borzilleri, R. M.; Vite, G. D. Discovery of ixabepilone (IXEMPRA), a first-in-class epothilone analog for treatment of metastatic breast cancer Annu. Rep. Med. Chem. 2009, 44, 301 - 322
12. Borzilleri, R. M.; Vite, G. D. Epothilones: new tubulin polymerization agents in preclinical and clinical development Drugs Future 2002, 27, 1149 - 1163
13. Hecht, S. M. Bleomycin: new perspectives on the mechanism of action J. Nat. Prod. 2000, 63, 158 - 168
14. Hecht, S. M. The chemistry of activated bleomycin Acc. Chem. Res. 1986, 19, 383 - 391
15. Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Thiopeptide antibiotics Chem. Rev. 2005, 105, 685 - 714
16. Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery J. Med. Chem. 2014, 57, 2832 - 2842
17. Choi-Sledeski, Y. M.; Kearney, R.; Poli, G.; Pauls, H.; Gardner, C.; Gong, Y.; Becker, M.; Davis, R.; Spada, A.; Liang, G.; Chu, V.; Brown, K.; Collussi, D.; Leadley, R., Jr.; Rebello, S.; Moxey, P.; Morgan, S.; Bentley, R.; Kasiewski, C.; Maignan, S.; Guilloteau, J.-P.; Mikol, V. Discovery of an orally efficacious inhibitor of coagulation factor Xa which incorporates a neutral P1 ligand J. Med. Chem. 2003, 46, 681 - 684
18. Roehrig, S.; Straub, A.; Pohlmann, J.; Lampe, T.; Pernerstorfer, J.; Schlemmer, K.-H.; Reinemer, P.; Perzborn, E. Discovery of the novel antithrombotic agent 5-chloro- N -({(5 S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide (BAY 59-7939): an oral, direct factor Xa inhibitor J. Med. Chem. 2005, 48, 5900 - 5908
19. Perzborn, E.; Roehrig, S.; Straub, A.; Kubitza, D.; Misselwitz, F. The discovery and development of rivaroxaban, an oral, direct factor Xa inhibitor Nature Rev. Drug Discovery 2011, 10, 61 - 75
20. Chan, C.; Borthwick, A. D.; Brown, D.; Burns-Kurtis, C. L.; Campbell, M.; Chaudry, L.; Chung, C.-w.; Convery, M. A.; Hamblin, J. N.; Johnstone, L.; Kelly, H. A.; Kleanthous, S.; Patikis, A.; Patel, C.; Pateman, A. J.; Senger, S.; Shah, G. P.; Toomey, J. R.; Watson, N. S.; Weston, H. E.; Whitworth, C.; Young, R. J.; Zhou, P. Factor Xa inhibitors: S1 binding interactions of a series of N -{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides J. Med. Chem. 2007, 50, 1546 - 1557
21. Lu, Y.; Shi, T.; Wang, Y.; Yang, H.; Yan, X.; Luo, X.; Jiang, H.; Zhu, W. Halogen bonding-a novel interaction for rational drug design? J. Med. Chem. 2009, 52, 2854 - 2862
22. Wilcken, R.; Zimmermann, M. O.; Lange, A.; Joerger, A. C.; Boeckler, F. M. Principles and applications of halogen bonding in medicinal chemistry and chemical biology J. Med. Chem. 2013, 56, 1363 - 1388
23. Sirimulla, S.; Bailey, J. B.; Vegesna, R.; Narayan, M. Halogen interactions in protein-ligand complexes: implications of halogen bonding for rational drug design J. Chem. Inf. Model. 2013, 53, 2781 - 2791
24. Hardegger, L. A.; Kuhn, B.; Spinnler, B.; Anselm, L.; Ecabert, R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz, J.; Plancher, J.-M.; Hartmann, G.; Banner, D. W.; Haap, W.; Diederich, F. Systematic investigation of halogen bonding in protein-ligand interactions Angew. Chem., Int. Ed. 2011, 50, 314 - 318
25. Scholfield, M. R.; Zanden, C. M. V.; Carter, M.; Ho, P. S. Halogen bonding (X-bonding): a biological perspective Protein Sci. 2013, 22, 139 - 152
26. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. Halogen bonding: the σ-hole J. Mol. Model. 2007, 13, 291 - 296
27. Politzer, P.; Murray, J. S.; Clark, T. Halogen bonding and other σ-hole interactions: a perspective Phys. Chem. Chem. Phys. 2013, 15, 11178 - 11189
28. Ibrahaim, M. A. A. Molecular mechanical study of halogen bonding in drug discovery J. Comput. Chem. 2011, 32, 2564 - 2574
29. Desiraju, G. R.; Ho, P. S.; Kloo, L.; Anthony C. Legon, A. C.; Marquardt, R.; Metrangolo, P.; Politzer, P.; Resnati, G.; Rissanen, K. Definition of the halogen bond (IUPAC Recommendations 2013) Pure Appl. Chem. 2013, 85, 1711 - 1713
30. Matter, H.; Nazaré, M.; Güssregen, S.; Will, D. W.; Schreuder, H.; Bauer, A.; Urmann, M.; Ritter, K.; Wagner, M.; Wehner, V. Evidence for C-Cl/C-Br···π interactions as an important contribution of protein-ligand binding affinity Angew. Chem., Int. Ed. 2009, 48, 2911 - 2916
31. Brameld, K. A.; Kuhn, B.; Reuter, D. C.; Stahl, M. Small molecule conformational preferences derived from crystal structure data. A medicinal chemistry focused analysis J. Chem. Inf. Model. 2008, 48, 1 - 24
32. Schärfer, C.; Schulz-Gasch, T.; Ehrlich, H.-C.; Guba, W.; Rarey, M.; Stahl, M. Torsion angle preferences in druglike chemical space: a comprehensive guide J. Med. Chem. 2013, 56, 2016 - 2028
33. Mann, A. Conformational restriction and/or steric hindrance in medicinal chemistry. In The Practice of Medicinal Chemistry, 2nd ed.; Wermuth, C. G., Ed.; Academic Press: London, 1996; pp 233 - 250.
34. Kuhn, B.; Mohr, P.; Stahl, M. Intramolecular hydrogen bonding in medicinal chemistry J. Med. Chem. 2010, 53, 2601 - 2611
35. Shalaeva, M.; Caron, G.; Abramov, Y. A.; O'Connell, T. N.; Plummer, M. S.; Yalamanchi, G.; Farley, K. A.; Goetz, G. H.; Philippe, L.; Shapiro, M. J. Integrating intramolecular hydrogen bonding (IMHB) considerations in drug discovery using ΔlogP as a tool J. Med. Chem. 2013, 56, 4870 - 4879
36. Yu, K. L.; Johnson, R. L. Synthesis and chemical properties of tetrazole peptide analogues J. Org. Chem. 1987, 52, 2051 - 2059
37. Zabrocki, J.; Marshall, G. R. The 1,5-disubstituted tetrazole ring as a cis -amide bond surrogate Methods Mol. Med. 1998, 23, 417 - 436
38. Venkatraman, S.; Njoroge, F. G. Macrocyclic inhibitors of HCV NS3 protease Exp. Opin. Ther. Pat. 2009, 19, 1277 - 1303
39. Giordanetto, F.; Kihlberg, J. Macrocyclic drugs and clinical candidates: what can medicinal chemists learn from their properties? J. Med. Chem. 2014, 57, 278 - 295
40. Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erikson-Viitanen, S. Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors Science 1994, 263, 380 - 384
41. Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; DeLucca, G. V.; Eyermann, C. J.; Chang, C.-H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Li, R.; Markwalder, J. A.; Seitz, S. P.; Sharpe, T. R.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; Erickson-Viitanen, S.; Hodge, C. N. Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2′ structure-activity relationship, and molecular recognition of cyclic ureas J. Med. Chem. 1996, 39, 3514 - 3525
42. Bryan, M. C.; Falsey, J. R.; Frohn, M.; Reichelt, A.; Yao, G.; Bartberger, M. D.; Bailis, J. M.; Zalameda, L.; San Miguel, T.; Doherty, E. M.; Allen, J. G. N-Substituted azaindoles as potent inhibitors of Cdc7 kinase Bioorg. Med. Chem. Lett. 2013, 23, 2056 - 2060
43. Chien, R. J.; Corey, E. J. Strong conformational preferences of heteroaromatic ethers and electron pair repulsion Org. Lett. 2010, 12, 132 - 135
44. Zimmer, L. E.; Sparr, C.; Gilmour, R. Fluorine conformational effects in organocatalysis: an emerging strategy for molecular design Angew. Chem., Int. Ed. 2011, 50, 11860 - 11871
45. Schüler, M.; O'Hagan, D.; Slawin, A. M. Z. The vicinal F-C-C-F moiety as a tool for influencing peptide conformation Chem. Commun. 2005, 4324 - 4326
46. Dudkin, V. Y. Bioisosteric equivalence of five-membered heterocycles Chem. Heterocycl. Compd. 2012, 48, 27 - 32
47. Nagao, Y. Chemical pharma-sciences that incorporate non-covalent bonded interactions Heterocycles 2013, 87, 1 - 29
48. Iwaoka, M.; Isozumi, N. Hypervalent non-bonded interactions of a divalent sulfur atom. Implications in protein architecture and the functions Molecules 2012, 17, 7266 - 7283
49. Murray, J. S.; Lane, P.; Politzer, P. Simultaneous σ-hole and hydrogen bonding by sulfur- and selenium-containing heterocycles Int. J. Quantum Chem. 2008, 108, 2770 - 2781
50. Pierce, A. C.; ter Haar, E.; Binch, H. M.; Kay, D. P.; Patel, S. R.; Li, P. CH···O and CH···N hydrogen bonds in ligand design: a novel quinazolin-4-ylthiazol-2-ylamine protein kinase inhibitor J. Med. Chem. 2005, 48, 1278 - 1281
51. Lin, S.; Wrobleski, S. T.; Hynes, J., Jr.; Pitt, S.; Zhang, R.; Fan, Y.; Doweyko, A. M.; Kish, K. F.; Sack, J. S.; Malley, M. F.; Kiefer, S. E.; Newitt, J. A.; McKinnon, M.; Trzaskos, J.; Barrish, J. C.; Dodd, J. H.; Schieven, G. L.; Leftheris, K. Utilization of a nitrogen-sulfur nonbonding interaction in the design of new 2-aminothiazol-5-yl-pyrimidines as p38α MAP kinase inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 5864 - 5868
52. Jackson, N. E.; Savoie, B. M.; Kohlstedt, K. L.; Olvera de la Cruz, M.; Schatz, G. C.; Chen, L. X.; Ratner, M. A. Controlling conformations of conjugated polymers and small molecules: the role of nonbonding interactions J. Am. Chem. Soc. 2013, 135, 10475 - 10483
53. Akiba, K.; Tsuchiya, T.; Inamoto, N.; Onuma, K.; Nagashima, N.; Nakamura, A. Chemistry of hypervalent sulfur. IV. The structure of the 1:1 adduct of "Hector's base" with arylcyanamides. Bond switch on hypervalent sulfur Chem. Lett. 1976, 723 - 726
54. Akiba, K.; Tsuchiya, Y.; Inamoto, N. Chemistry of hypervalent sulfur. V. A 13C-NMR study of the 1:1 adduct of "Hector's base" with arylcyanamides. Evidence for intramolecular S···N interaction Tetrahedron Lett. 1976, 17, 3819 - 3820
55. Ghosh, R.; Simonsen, S. H. Structure of 2-(2′-thienyl)pyridine at 193 K Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, C49, 1031 - 1032
56. Yu, J. Y.; Yoo, C. L.; Yang, B.; Lodewyk, M. W.; Meng, L.; El-Idreesy, T. T.; Fettinger, J. C.; Tantillo, D. J.; Verkman, A. S.; Kurth, M. J. Potent s-cis-locked bithiazole correctors of ΔF508 cystic fibrosis transmembrane conductance regulator cellular processing for cystic fibrosis therapy J. Med. Chem. 2008, 51, 6044 - 6054
57. Rittner, R.; Ducati, L. C.; Tormena, C. F.; Fiorin, B. C.; Braga, C. B. Conformational preferences for some 5-substituted 2-acetylthiophenes through infrared spectroscopy and theoretical calculations Spectrochim. Acta, Part A 2011, 79, 1071 - 1076
58. Weinhold, F.; Landis, C. R. Natural bond orbitals and extensions of localized bonding concepts Chem. Educ. Res. Pract. Eur. 2001, 2, 91 - 104
59. Ducati, L. C.; Braga, C. B.; Rittner, R.; Tormena, C. F. A critical evaluation of the s-cis-trans isomerism of 2-acetylpyrrole and its N -methyl derivative through infrared and NMR spectroscopies and theoretical calculations Spectrochim. Acta, Part A 2013, 116, 196 - 203
60. Rittner, R.; Ducati, L. C.; Tormena, C. F.; Cormanich, R. A.; Fiorin, B. C.; Braga, C. B.; Abraham, R. J. Studies on the s-cis-trans isomerism for some furan derivatives through IR and NMR spectroscopies and theoretical calculations Spectrochim. Acta, Part A 2013, 103, 84 - 89
61. Gökce, H.; Bahçeli, S. Analysis of molecular structure and vibrational spectra of 2-(2′-thienyl)pyridine J. Mol. Struct. 2011, 1005, 100 - 106
62. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley & Sons: New York, 1976.
63. Bartberger, M. D.; Tantillo, D. J. Work in progress-the effect of substituents and ring composition on such donor-acceptor interactions is a current area of study in our two groups and will be reported in due course.
64. Sims, P. A.; Wong, C. F.; Vuga, D.; McCammon, J. A.; Sefton, B. M. Relative contributions of desolvation, inter- and intra-molecular interactions to binding affinity in protein kinase systems J. Comput. Chem. 2005, 26, 668 - 681
65. Hitchcock, S. A.; Pennington, L. D. Structure-brain exposure relationships J. Med. Chem. 2006, 49, 7559 - 7583
66. Jorgensen, W. L.; Schyman, P. Treatment of halogen bonding in the OPLS-AA force field: application to potent anti-HIV agents J. Chem. Theory Comput. 2012, 8, 3895 - 3901
67. St. Jean, D. J., Jr.; Fotsch, C. Mitigating heterocycle metabolism in drug discovery J. Med. Chem. 2012, 55, 6002 - 6020
68. Edwards, P. D.; Wolanin, D. J.; Andisik, D. W.; Davis, M. W. Peptidyl α-ketoheterocyclic inhibitors of human neutrophil elastase. 2. Effect of varying the heterocyclic ring on in vitro potency J. Med. Chem. 1995, 38, 76 - 85
69. Maryanoff, B. E.; Costanzo, M. J. Inhibitors of proteases and amide hydrolases that employ an α-ketoheterocycle as a key enabling functionality Bioorg. Med. Chem. 2008, 16, 1562 - 1595
70. Ángyán, J. G.; Poirer, R. A.; Kucsman, Á.; Csizmadia, I. G. Bonding between nonbonded sulfur and oxygen atoms in selected organic molecules (a quantum chemical study) J. Am. Chem. Soc. 1987, 109, 2237 - 2245
71. Markham, G. D.; Bock, C. W. Intramolecular sulfur-oxygen interactions: an ab initio molecular orbital and density functional theory investigation J. Mol. Struct.: THEOCHEM 1997, 418, 139 - 154
72. Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. Synthesis and antiviral activity of certain thiazole C-nucleosides J. Med. Chem. 1977, 20, 256 - 262
73. Goldstein, B. M.; Takusagawa, F.; Berman, H. M.; Srivastava, P. C.; Robins, R. K. Structural studies of a new antitumor agent: tiazofurin and its inactive analogues J. Am. Chem. Soc. 1983, 105, 7416 - 7422
74. Gebeyehu, G.; Marquez, V. E.; Van Cott, A.; Cooney, D. A.; Kelley, J. A.; Jayaram, H. N.; Ahluwalia, G. S.; Dion, R. L.; Wilson, Y. A.; Johns, D. G. Ribavirin, tiazofurin, and selenazofurin: mononucleotides and nicotinamide adenine dinucleotide analogs. Synthesis, structure, and interactions with IMP dehydrogenase J. Med. Chem. 1985, 28, 99 - 105
75. Goldstein, B. M.; Takusagawa, F.; Berman, H. M.; Srivastava, P. C.; Robins, R. K. Structural studies of a new antitumor and antiviral agent: selenazofurin and its α anomer J. Am. Chem. Soc. 1985, 107, 1394 - 1400
76. Streeter, D. G.; Robins, R. K. Comparative in vitro studies of tiazofurin and a selenazole analog Biochem. Biophys. Res. Commun. 1983, 115, 544 - 550
77. Goldstein, B. M.; Mao, D. T.; Marquez, V. E. Ara-tiazofurin: conservation of structural features in an unusual thiazole nucleoside J. Med. Chem. 1988, 31, 1026 - 1031
78. Goldstein, B. M.; Colby, T. D. Conformational constraints in NAD analogs: implications for dehydrogenase binding and specificity Adv. Enzyme Regul. 2000, 40, 405 - 426
79. Jayaram, H. N.; Dion, R. L.; Glazer, R. I.; Johns, D. G.; Robins, R. K.; Srivastava, P. C.; Cooney, D. A. Initial studies on the mechanism of action of a new oncolytic thiazole nucleoside, 2-β- d -ribofuranosylthiazole-4-carboxamide (NSC 286193) Biochem. Pharmacol. 1982, 31, 2371 - 2380
80. Tiazofurin: molecular and clinical action. Weber, G.; Prajda, N.; Abonyi, M.; Look, K. Y.; Tricot, G. Anticancer Res. 1996, 16, 3313 - 3322
81. Goldstein, B. M.; Bell, J. E.; Marquez, V. E. Dehydrogenase binding by tiazofurin anabolites J. Med. Chem. 1990, 33, 1123 - 1127
82. Li, H.; Goldstein, B. M. Carboxamide group conformation in the nicotinamide and thiazole-4-carboxamide rings: implications for enzyme binding J. Med. Chem. 1992, 35, 3560 - 3567
83. Burling, F. T.; Goldstein, B. M. Computational studies of nonbonded sulfur-oxygen and selenium-oxygen interactions in the thiazole and selenazole nucleosides J. Am. Chem. Soc. 1992, 114, 2313 - 2320
84. Makara, G. M.; Keseruî, G. M. On the conformation of tiazofurin analogues J. Med. Chem. 1997, 40, 4154 - 4159
85. Li, H.; Hallows, W. H.; Punzi, J. S.; Marquez, V. E.; Carrell, H. L.; Pankiewicz, K. W.; Watanabe, K. A.; Goldstein, B. M. Crystallographic studies of two alcohol dehydrogenase-bound analogues of thiazole-4-carboxamide adenine dinucleotide (TAD), the active anabolite of the antitumor agent tiazofurin Biochemistry 1994, 33, 23 - 32
86. Jayaram, H. N.; Ahluwalia, G. S.; Dion, R. L.; Gebeyehu, G.; Marquez, V. E.; Kelley, J. A.; Robins, R. K.; Cooney, D. A.; Johns, D. G. Conversion of 2-β- d -ribofuranosylselenazole-4-carboxamide to an analog of NAD with potent IMP dehydrogenase-inhibitory properties Biochem. Pharmacol. 1983, 32, 2633 - 2636
87. Li, M.; Dyda, F.; Benhart, I.; Pastant, I.; Davies, D. R. Crystal structure of the catalytic domain of Pseudomonas exotoxin A complexed with a nicotinamide adenine dinucleotide analog: implications for the activation process and for ADP ribosylation Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 6902 - 6906
88. Colby, T. D.; Vanderveen, K.; Strickler, M. D.; Markham, G. D.; Goldstein, B. M. Crystal structure of human type II inosine monophosphate dehydrogenase: implications for ligand binding and drug design Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 3531 - 3536
89. Franchetti, P.; Cristalli, G.; Grifantini, M.; Cappellacci, L.; Vittori, S.; Nocentini, G. Synthesis and antitumor activity of 2-β- d -ribofuranosyloxazole-4-carboxamide (oxazofurin) J. Med. Chem. 1990, 33, 2849 - 2852
90. Goldstein, B. M.; Li, H.; Hallows, W. H.; Langs, D. A.; Franchetti, P.; Cappellacci, L.; Grifantini, M. C-Glycosyl bond conformation in oxazofurin: crystallographic and computational studies of the oxazoles analogue of tiazofurin J. Med. Chem. 1994, 37, 1684 - 1688
91. Franchetti, P.; Cappellacci, L.; Grifantini, M.; Barzi, A.; Nocentini, G.; Yang, H.; O'Connor, A.; Jayaram, H. N.; Carrell, C.; Goldstein, B. M. Furanfurin and thiophenfurin: two novel tiazofurin analogues. Synthesis, structure, antitumor activity, and interactions with inosine monophosphate dehydrogenase J. Med. Chem. 1995, 38, 3829 - 3837
92. Franchetti, P.; Cappellacci, L.; Perlini, P.; Jayaram, H. N.; Buler, A.; Schneider, B. P.; Collart, F. R.; Huberman, E.; Grifantini, M. Isosteric analogues of nicotinamide adenine dinucleotide derived from furanfurin, thiophenfurin, and selenophenfurin as mammalian inosine monophosphate dehydrogenase (type I and II) inhibitors J. Med. Chem. 1998, 41, 1702 - 1707
93. Franchetti, P.; Marchetti, S.; Cappellacci, L.; Yalowitz, J. A.; Jayaram, H. N.; Goldstein, B. M.; Grifantini, M. A new C -nucleoside analogue of tiazofurin: synthesis and biological evaluation of 2-β-D-ribofuranosylimidazole-4-carboxamide (imidazofurin) Bioorg. Med. Chem. Lett. 2001, 11, 67 - 69
94. Popsavin, M.; Spaić, S.; Svirčev, M.; Kojić, V.; Bogdanović, G.; Popsavin, V. Synthesis and in vitro antitumour screening of 2-(β-D-xylofuranosyl)thiazole-4-carboxamide and two novel tiazofurin analogues with substituted tetrahydrofurodioxole moiety as a sugar mimic Bioorg. Med. Chem. Lett. 2012, 22, 6700 - 6704
95. Zatorski, A.; Watanabe, K. A.; Carr, S. F.; Goldstein, B. M.; Pankiewicz, K. W. Chemical synthesis of benzamide adenine dinucleotide: inhibition of inosine monophosphate dehydrogenase (types I and II) J. Med. Chem. 1996, 39, 2422 - 2426
96. Franchetti, P.; Marchetti, S.; Cappellacci, L.; Jayaram, H. N.; Yalowitz, J. A.; Goldstein, B. M.; Barascut, J.-L.; Dukhan, D.; Imbach, J.-L.; Grifantini, M. Synthesis, conformational analysis, and biological activity of C-thioribonucleosides related to tiazofurin J. Med. Chem. 2000, 43, 1264 - 1270
97. Shin, D.; Sinkeldam, R. W.; Tor, Y. Emissive RNA alphabet J. Am. Chem. Soc. 2011, 133, 14912 - 14915
98. Sinkeldam, R. W.; McCoy, L. S.; Shin, D.; Tor, Y. Enzymatic interconversion of isomorphic fluorescent nucleosides: adenosine deaminase transforms an adenosine analogue into an inosine analogue Angew. Chem., Int. Ed. 2013, 52, 14026 - 14030
99. Camm, A. J.; Bounameaux, H. Edoxaban: a new oral direct factor Xa inhibitor Drugs 2011, 71, 1503 - 1526
100. Escolar, G.; Diaz-Ricart, M. Edoxaban tosilate: direct factor Xa inhibitor prevention of post-operative venous thromboembolism treatment of atrial fibrillation Drugs Future 2009, 34, 861 - 872
101. Haginoya, N.; Kobayashhi, S.; Komoriya, S.; Yoshino, T.; Suzuki, M.; Shimada, T.; Watanabe, K.; Hirokawa, Y.; Furugori, T.; Nagahara, T. Synthesis and conformational analysis of a non-amidine factor Xa inhibitor that incorporates 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4- c ]pyridine as S4 binding element J. Med. Chem. 2004, 47, 5167 - 5182
102. Komoriya, S.; Kobayashi, S.; Osanai, K.; Yoshino, T.; Nagata, T.; Haginoya, N.; Nakamoto, Y.; Mochizuki, A.; Nagahara, T.; Suzuki, M.; Shimada, T.; Watanabe, K.; Isobe, Y.; Furugoori, T. Design, synthesis, and biological activity of novel factor Xa inhibitors: Improving metabolic stability by S1 and S4 ligand modification Bioorg. Med. Chem. 2006, 14, 1309 - 1330
103. Nagata, T.; Yoshino, T.; Haginoya, N.; Yoshikawa, K.; Nagamochi, M.; Kobayashi, S.; Komoriya, S.; Yokomizo, A.; Muto, R.; Yamaguchi, M.; Osanai, K.; Suzuki, M.; Kanno, H. Discovery of N -[(1 R,2 S,5 S)-2-{[(5-chloroindol-2-yl)carbonyl]amino}-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4- c ]pyridine-2-carboxamide hydrochloride: a novel, potent and orally active direct inhibitor of factor Xa Bioorg. Med. Chem. 2009, 17, 1193 - 1206
104. Yoshikawa, K.; Kobayashi, S.; Nakamoto, Y.; Haginoya, N.; Komoriya, S.; Yoshino, T.; Nagata, T.; Mochizuki, A.; Watanabe, K.; Suzuki, M.; Kanno, H.; Ohta, T. Design, synthesis, and SAR of cis -1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part II: exploration of 6-6 fused rings as alternative S1 moieties Bioorg. Med. Chem. 2009, 17, 8221 - 8233
105. Adler, M.; Kochanny, M. J.; Ye, B.; Rumennik, G.; Light, D. R.; Biancalana, S.; Whitlow, M. Crystal structures of two potent nonamidine inhibitors bound to factor Xa Biochemistry 2002, 41, 15514 - 15523
106. Guba, W.; Neidhart, W.; Nettekoven, M. Novel and potent NPY5 receptor antagonists derived from virtual screening and iterative parallel chemistry design Bioorg. Med. Chem. Lett. 2005, 15, 1599 - 1603
107. Nettekoven, M.; Guba, W.; Neidhart, W.; Mattei, P.; Pflieger, P.; Roche, O.; Taylor, S. Isomeric thiazole derivative as ligands for the neuropeptide Y5 receptor Bioorg. Med. Chem. Lett. 2005, 15, 3446 - 3449
108. Nettekoven, M.; Guba, W.; Neidhart, W.; Mattei, P.; Pflieger, P.; Plancher, J.-M.; Taylor, S. Aminothiazole derivatives as neuropeptide Y5 receptor ligands: finding the balance between affinity and physicochemical properties ChemMedChem 2006, 1, 45 - 48
109. Gibson, S.; McGuire, R.; Rees, D. C. Principal components describing biological activities and molecular diversity of heterocyclic aromatic ring fragments J. Med. Chem. 1996, 39, 4065 - 4072
110. Breitung, E. M.; Shu, C.-F.; McMahon, R. J. Thiazole and thiophene analogues of donor-acceptor stilbenes: molecular hyperpolarizabilities and structure-property relationships J. Am. Chem. Soc. 2000, 122, 1154 - 1160
111. Reid, R. C.; Yau, M.-K.; Singh, R.; Hamidon, J. K.; Reed, A. N.; Chu, P.; Suen, J. Y.; Stoermer, M. J.; Blakeney, J. S.; Lim, J.; Faber, J. M.; Fairlie, D. P. Downsizing a human inflammatory protein to a small molecule with equal potency and functionality Nature Commun. 2013, 4 2802 10.1038/ncomms3802
112. Reid, R. C.; Yau, M.-K.; Singh, R.; Lim, J.; Fairlie, D. P. Stereoelectronic effects dictate molecular conformation and biological function of heterocyclic amides J. Am. Chem. Soc. 2014, 136, 11914 - 11917
113. Mathieu, L.; Legrand, B.; Dang, C.; Vezenkov, L.; Wenger, E.; Didierjean, C.; Amblard, M.; Avrlant-Petit, M.-C.; Masurier, N.; Lisowski, V.; Martinez, J.; Maillard, L. T. Helical oligomers of thiazole-based γ-amino acids: synthesis and structural studies Angew. Chem., Int. Ed. 2013, 52, 6006 - 6010
114. Legrand, B.; Mathieu, L.; Lebrun, A.; Andriamanarivo, S.; Lisowski, V.; Masurier, N.; Zirah, S.; Kamg, Y. K.; Martinez, J.; Maillard, L. T. Thiazole-based γ-building blocks as reverse-turn mimetic to design a gramicidin S analogue: conformational and biological evaluation Chem.-Eur. J. 2014, 20, 6713 - 6720
115. Hynes, J., Jr.; Wu, H.; Pitt, S.; Shen, D. R.; Zhang, R.; Schieven, G. L.; Gillooly, K. M.; Shuster, D. J.; Taylor, T. L.; Yang, X.-X.; McIntyre, K. W.; McKinnon, M.; Zhang, H.; Marathe, P. H.; Doweyko, A. M.; Kish, K.; Kiefer, S. E.; Sack, J. S.; Newitt, J. A.; Barrish, J. C.; Dodd, J.; Leftheris, K. The discovery of (R)-2-(sec -butylamino)- N -(2-methyl-5-(methylcarbamoyl)phenyl)-thiazole-5-carboxamide (BMS-640994)-a potent and efficacious p38α MAP kinase inhibitor Bioorg. Med. Chem. Lett. 2008, 18, 1762 - 1767
116. Wrobleski, S. T.; Lin, S.; Dhar, T. G. M.; Dyckman, A. J.; Li, T.; Pitt, S.; Zhang, R.; Fan, Y.; Doweyko, A. M.; Tokarski, J. S.; Kish, K. F.; Kiefer, S. E.; Sack, J. S.; Newitt, J. A.; Witmer, M. R.; McKinnon, M.; Barrish, J. C.; Dodd, J. H.; Schieven, G. L.; Leftheris, K. The identification of novel p38α isoform selective kinase inhibitors having an unprecedented p38α binding mode Bioorg. Med. Chem. Lett. 2013, 23, 4120 - 4126
117. Lombardo, L. J.; Lee, F. Y.; Chen, P.; Norris, D.; Barrish, J. C.; Behnia, K.; Castaneda, S.; Cornelius, L. A. M.; Das, J.; Doweyko, A. M.; Fairchild, C.; Hunt, J. T.; Inigo, I.; Johnston, K.; Kamath, A.; Kan, D.; Klei, H.; Marathe, P.; Pang, S.; Peterson, R.; Pitt, S.; Schieven, G. L.; Schmidt, R. J.; Tokarski, J.; Wen, M.-L.; Wityak, J.; Borzilleri, R. M. Discovery of N -(2-chloro-6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide (BMS-354825), a dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays J. Med. Chem. 2004, 47, 6658 - 6661
118. Das, J.; Chen, P.; Norris, D.; Padmanabha, R.; Lin, J.; Moquin, R. V.; Shen, Z.; Cook, L. S.; Doweyko, A. M.; Pitt, S.; Pang, S.; Ren Shen, D.; Fang, Q.; Fex, H. F.; McIntyre, K. W.; Shuster, D. J.; Gillooly, K. M.; Behnia, K.; Schieven, G. L.; Wityak, J.; Barrish, J. C. 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N -(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan -Src kinase inhibitor J. Med. Chem. 2006, 49, 6819 - 6832
119. Tokarski, J. S.; Newitt, J.; Chang, C. Y. J.; Cheng, J. D.; Wittekind, M.; Kiefer, S. E.; Kish, K.; Lee, F. Y. F.; Borzilerri, R.; Lombardo, L. J.; Xie, D.; Zhang, Y.; Klei, H. E. The structure of dasatinib (BMS-354825) bound to activated ABL kinase domain elucidates its inhibitory activity against imatinib-resistant ABL mutants Cancer Res. 2006, 66, 5790 - 5797
120. Getlik, M.; Grutter, C.; Simard, J. R.; Kluter, S.; Rabiller, M.; Rode, H. B.; Robubi, A.; Rauh, D. Hybrid compound design to overcome the gatekeeper T338M mutation in cSrc J. Med. Chem. 2009, 52, 3915 - 3926
121. Farenc, C. J. A.; Hameetman, L.; Zoutman, W.; Tensen, C. P.; Siegal, G. Crystal structure of the EphA4 protein tyrosine kinase domain in the apo- and dasatinib-bound state FEBS Lett. 2011, 585, 3593 - 3599
122. Williams, N. K.; Lucet, I. S.; Klinken, S. P.; Ingley, E.; Rossjohn, J. Crystal structures of the Lyn protein tyrosine kinase domain in its apo- and inhibitor bound state J. Biol. Chem. 2009, 284, 284 - 291
123. Muckelbauer, J.; Sack, J. S.; Ahmed, N.; Burke, J.; Chang, C. Y.; Gao, M.; Tino, J.; Xie, D.; Tebben, A. J. X-ray crystal structure of bone marrow kinase in the X chromosome: a Tec family kinase Chem. Biol. Drug Des. 2011, 78, 739 - 748
124. Marcotte, D. J.; Liu, Y. T.; Arduini, R. M.; Hession, C. A.; Miatkowski, K.; Wildes, C. P.; Cullen, P. F.; Hong, V.; Hopkins, B. T.; Mertsching, E.; Jenkins, T. J.; Romanowski, M. J.; Baker, D. P.; Silvian, L. F. Structures of human Bruton's tyrosine kinase in active and inactive conformations suggest a mechanism of activation for TEC family kinases Protein Sci. 2010, 19, 429 - 439
125. Disch, J. S.; Evindar, G.; Chiu, C. H.; Blum, C. A.; Dai, H.; Jin, L.; Schuman, E.; Lind, K. E.; Belyanskaya, S. L.; Deng, J.; Coppo, F.; Aquilani, L.; Graybill, T. L.; Cuozzo, J. W.; Lavu, S.; Mao, C.; Vlasuk, G. P.; Perni, R. B. Discovery of thieno[3,2- d ]pyrimidine-6-carboxamides as potent inhibitors of SIRT1, SIRT2, and SIRT3 J. Med. Chem. 2013, 56, 3666 - 3679
126. Brument, S.; Sivignon, A.; Dumych, T. I.; Moreau, N.; Roos, G.; Guérardel, Y.; Chalopin, T.; Deniaud, D.; Bilyy, R. O.; Darfeuille-Michaud, A.; Bouckaert, J.; Gouin, S. G. Thiazolylaminomannosides as potent antiadhesives of type 1 piliated Escherichia coli isolated from Crohn's disease patients J. Med. Chem. 2013, 56, 5395 - 5406
127. Laha, J. K.; Zhang, X.; Qiao, L.; Liu, M.; Chatterjee, S.; Robinson, S.; Kosik, K. S.; Cuny, G. D. Structure-activity relationship study of 2,4-diaminothiazoles as Cdk5/p25 kinase inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 2098 - 2101
128. Ahn, J. S.; Radhakrishnan, M. L.; Mapelli, M.; Choi, S.; Tidor, B.; Cuny, G. D.; Musacchio, A.; Yeh, L.-A.; Kosik, K. S. Defining Cdk5 ligand chemical space with small molecule inhibitors of tau phosphorylation Chem. Biol. 2005, 12, 811 - 823
129. Schonbrunn, E.; Betzi, S.; Alam, R.; Martin, M. P.; Becker, A.; Han, H.; Francis, R.; Chakrasali, R.; Jakkaraj, S.; Kazi, A.; Sebti, S. M.; Cubitt, C. L.; Gebhard, A. W.; Hazlehurst, L. A.; Tash, J. S.; Georg, G. I. Development of highly potent and selective diaminothiazole inhibitors of cyclin-dependent kinases J. Med. Chem. 2013, 56, 3768 - 3782
130. Tanaka, R.; Oyama, Y.; Imajo, S.; Matsuki, S.; Ishiguro, M. Structure-activity relationships of penem antibiotics: crystallographic structures and implications for their antimicrobial activities Bioorg. Med. Chem. 1997, 5, 1389 - 1399
131. Rochel, N.; Moras, D. Crystal structure of a vitamin D3 analogue, ZK203278, showing dissociated profile Anticancer Res. 2012, 32, 335 - 340
132. Huang, Q.; Johnson, T. W.; Bailey, S.; Brooun, A.; Bunker, K. D.; Burke, B. J.; Collins, M. R.; Cook, A. S.; J. Cui, J.; Dack, K. N.; Deal, J. G.; Deng, Y.-L.; Dinh, D.; Engstrom, L. D.; He, M.; Hoffman, J.; Hoffman, R. L.; Johnson, P. S.; Kania, R. S.; Lam, H.; Lam, J. L.; Le, P. T.; Li, Q.; Lingardo, L.; Liu, W.; West Lu, M.; McTigue, M.; Palmer, C. L.; Richardson, P. F.; Sach, N. W.; Shen, H.; Smeal, T.; Smith, G. L.; Stewart, A. E.; Timofeevski, S.; Tsaparikos, K.; Wang, H.; Zhu, H.; Zhu, J.; Zou, H. Y.; Edwards, M. P. Design of potent and selective inhibitors to overcome clinical anaplastic lymphoma kinase mutations resistant to crizotinib J. Med. Chem. 2014, 57, 1170 - 1187
133. Rodríguez, S.; Kneeteman, M.; Izquierdo, J.; López, I.; González, F. V.; Peris, G. Diastereoselective synthesis of γ-hydroxy α,β-epoxyesters and their conversion into β-hydroxy α-sulfenyl γ-butyrolactones Tetrahedron 2006, 62, 11112 - 11123
134. González, F. V.; Jain, A.; Rodríguez, S.; Sáez, J. A.; Vicent, C.; Peris, G. Stereoisomerization of β-hydroxy-α-sulfenyl-γ-butyrolactones controlled by two concomitant 1,4-type nonbonded sulfur-oxygen interactions as analyzed by X-ray crystallography J. Org. Chem. 2010, 75, 5888 - 5894
135. Silverman, R. B. Mechanism of isomerization of a β-keto sulfide J. Org. Chem. 1981, 46, 4789 - 4791
136. Dubey, R.; Polaske, N. W.; Nichol, G. S.; Olenyuk, B. Efficient organocatalytic α-sulfenylation of substituted piperazine-2,5-diones Tetrahedron Lett. 2009, 50, 4310 - 4313
137. Wang, X.; Yang, T.; Cheng, X.; Shen, Q. Enantioselective electrophilic trifluoromethylthiolation of β-ketoesters: a case of reactivity and selectivity bias for organocatalysis Angew. Chem., Int. Ed. 2013, 52, 12860 - 12864
138. Bootwicha, T.; Liu, X.; Pluta, R.; Atodiresei, I.; Rueping, M. N -Trifluoromethylthiophthalimide: a stable electrophilic SCF3 reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation Angew. Chem., Int. Ed. 2013, 52, 12856 - 12859
139. Hiram, T.; Nomiyama, J.; Sakae, N.; Nishimura, K.; Yokomoto, M.; Inoue, S.; Tamura, K.; Okuhira, M.; Amano, H.; Nagao, Y. Acyliminothiadiazoline derivatives: new, highly potent, and orally active angiotensin II receptor antagonists Bioorg. Med. Chem. Lett. 1996, 6, 1469 - 1474
140. Hirata, T.; Goto, S.; Tamura, K.; Okuhira, M.; Nagao, Y. Quantitative structure-activity relationships of benzoyliminothiadiazoline derivatives as angiotensin II receptor antagonists Bioorg. Med. Chem. Lett. 1997, 7, 385 - 388
141. Nagao, Y.; Hirata, T.; Goto, S.; Sano, S.; Kakehi, A.; Iizuka, K.; Shiro, M. Intramolecular nonbonded S···O interaction recognized in (acylimino)thiadiazoline derivatives as angiotensin II receptor antagonists and related compounds J. Am. Chem. Soc. 1998, 120, 3104 - 3110
142. Meyer, E.; Joussef, A. C.; Gallardo, H.; Bortoluzzi, A. J.; Longo, R. L. 1,5-Type nonbonded O···S and S···S interactions in (acylimino) and (thioacylimino)benzothiazoline systems. Crystal structures and theoretical calculations Tetrahedron 2003, 59, 10187 - 10193
143. Nagao, Y.; Iimori, H.; Goto, S.; Hirata, T.; Sano, S.; Chuman, H.; Shiro, M. Remarkable discrepancy in the predominant structures of acyl (or thioacyl)iminothiadiazoles, acyl (or thioacyl)aminooxadiazoles and related compounds having the potential for rotational, geometrical and tautomeric isomerism Tetrahedron Lett. 2002, 43, 1709 - 1712
144. Manaka, A.; Sato, M.; Aoki, M.; Tanaka, M.; Ikeda, T.; Toda, Y.; Yamane, Y.; Nakaike, S. 2-Acylimino-3 H -thiazoline derivatives: a novel template for platelet gpIIb/IIIa receptor antagonists Bioorg. Med. Chem. Lett. 2001, 11, 1031 - 1035
145. Jeschke, P.; Nauen, R.; Beck, M. E. Nicotinic acetylcholine receptor agonists: a milestone for modern crop protection Angew. Chem., Int. Ed. 2013, 52, 9464 - 9485
146. Tomizawa, M.; Zhang, N.; Durkin, K. A.; Olmstead, M. M.; Casida, J. E. The neonicotinoid electronegative pharmacophore plays the crucial role in the high affinity and selectivity for the Drosophila nicotinic receptor: an anomaly for the nicotinoid cation-π interaction model Biochemistry 2003, 42, 7819 - 7827
147. Tomizawa, M.; Kagabu, S.; Ohno, I.; Durkin, K. A.; Casida, J. E. Potency and selectivity of trifluoroacetylimino and pyrazinoylimino nicotinic insecticides and their fit at a unique binding site niche J. Med. Chem. 2008, 51, 4213 - 4218
148. Ohno, I.; Tomizawa, M.; Aoshima, A.; Kumuzawa, S.; Kagabu, S. Trifluoroacetyl neonicotinoid insecticides with enhanced hydrophobicity and effectiveness J. Agric. Food Chem. 2010, 58, 4999 - 5003
149. Tomizawa, M.; Kagabu, S.; Casida, J. E. Receptor structure-guided neonicotinoid design J. Agric. Food Chem. 2011, 59, 2918 - 2922
150. Tomizawa, M.; Durkin, K. A.; Ohno, I.; Nagura, K.; Manabe, M.; Kumuzawa, S.; Kagabu, S. N -Haloacetylimino neonicotinoids: potency and molecular recognition at the insect nicotinic receptor Bioorg. Med. Chem. Lett. 2011, 21, 3583 - 3586
151. Nagao, Y.; Iimori, H.; Nam, K. H.; Sano, S.; Shiro, M. Synthesis and antibacterial activity of new 1β-methylcarbapenems having the potential for an intramolecular nonbonded S···O interactions Chem. Pharm. Bull. 2001, 49, 1660 - 1661
152. Park, H.; Hong, S.; Hong, S. Nocodazole is a high-affinity ligand for the cancer-related kinases ABL, cKIT, BRAF, and MEK ChemMedChem 2012, 7, 53 - 56
153. Park, H.; Hong, S.; Kim, J.; Hong, S. Discovery of picomolar ABL kinase inhibitors equipotent for wild type and T315I mutant via structure-based de novo design J. Am. Chem. Soc. 2013, 135, 8227 - 8237
154. Hong, S.; Kim, J.; Yun, S.-M.; Lee, H.; Park, Y.; Hong, S.-S.; Hong, S. Discovery of new benzothiazole-based inhibitors of breakpoint cluster region-Abelson kinase including the T315I mutant J. Med. Chem. 2013, 56, 3531 - 3545
155. Martins, F. T.; Neves, P. P.; Ellena, J.; Cami, G. E.; Brusau, E. V.; Narda, G. E. Intermolecular contacts influencing the conformational and geometric features of the pharmaceutically preferred mebendazole polymorph C J. Pharm. Sci. 2009, 98, 2336 - 2344
156. Okaniwa, M.; Hirose, M.; Imada, T.; Ohaashi, T.; Hayashai, Y.; Miyazaki, T.; Arita, T.; Yabuki, M.; Kakoi, K.; Kato, J.; Takagi, T.; Kawamoto, T.; Yao, S.; Sumita, A.; Tsutsumi, S.; Tottori, T.; Oki, H.; Sang, B.-C.; Yano, J.; Aertgeerts, K.; Yoshida, S.; Ishikawa, T. Design and synthesis of novel DFG-out RAF/vascular endothelial growth factor receptor 2 inhibitors. 1. Exploration of [5,6]-fused bicyclic scaffolds J. Med. Chem. 2012, 55, 3452 - 3478
157. Zhao, L.; Zhang, Y.; Dai, C.; Guzi, T.; Wiswell, D.; Seghezzi, W.; Parry, D.; Fischmann, T.; Siddiqui, M. A. Design, synthesis and SAR of thienopyridines as potent CHK1 inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 7216 - 7221
158. Murphy-Benenato, K.; Wang, H.; McGuire, H. M.; Davis, H. E.; Gao, N.; Prince, D. B.; Jahic, H.; Stokes, S. S.; Boriack-Sjodin, P. A. Identification through structure-based methods of a baceterial NAD+-dependent DNA ligase inhibitor that avoids known resistance mutations Bioorg. Med. Chem. Lett. 2014, 24, 360 - 366
159. Collins, I.; Moyes, C.; Davey, W. B.; Rowley, M.; Bromidge, F. A.; Quirk, K.; Atack, J. R.; McKernan, R. M.; Thompson, S.-A.; Wafford, K.; Dawson, G. R.; Pike, A.; Sohal, B.; Tsou, N. N.; Ball, R. G.; Castro, J. L. 3-Heteroaryl-2-pyridones: benzodiazepine site ligands with functional selectivity for α2/α3-subtypes of human GABAA receptor-ion channels J. Med. Chem. 2002, 45, 1887 - 1900
160. Corazón Félix-Sonda, B.; Rivera-Islas, J.; Herrera-Ruiz, D.; Morales-Rojas, H.; Höpfl, H. Nitazoxanide cocrystals in combination with succinic, glutaric and 2,5-dihydroxybenzoic acid Cryst. Growth Des. 2014, 14, 1086 - 1102
161. Grewal, A. S.; Sekhon, B. S.; Lather, V. Recent updates on glucokinase activators for the treatment of type 2 diabetes mellitus Mini-Rev. Med. Chem. 2014, 14, 585 - 602
162. Haynes, N.-E.; Corbett, W. L.; Bizzarro, F. T.; Guertine, K. R.; Hilliard, D. W.; Holland, G. W.; Kester, R. F.; Mahaney, P. E.; Qi, L.; Spence, C. L.; Tengi, J.; Dvorozniak, M. T.; Railkar, A.; Matschinsky, F. M.; Grippo, J. F.; Grimsby, J.; Sarabu, R. Discovery, structure-activity relationships, pharmacokinetics, and efficacy of glucokinase activator (2 R)-3-cyclopentyl-2-(4-methanesulfonylphenyl)-N-thiazole-2-yl-propionamide (RO0281675) J. Med. Chem. 2010, 53, 3618 - 3625
163. Cheruvallath, Z. S.; Gwaltney, S. L., II; Sabat, M.; Tang, M.; Feng, J.; Wang, H.; Miura, J.; Guntupalli, P.; Jennings, A.; Hosfield, D.; Lee, B.; Wu, Y. Design, synthesis and SAR of novel glucokinase activators Bioorg. Med. Chem. Lett. 2013, 23, 2166 - 2171
164. Nishimura, T.; Iino, T.; Mitsuya, M.; Bamba, M.; Watanabe, H.; Tsukahara, D.; Kamata, K.; Sasaki, K.; Ohyama, S.; Hosaka, H.; Futamura, M.; Nagata, Y.; Eiki, J.-i. Identification of novel and potent 2-amino benzamide derivatives as allosteric glucokinase activators Bioorg. Med. Chem. Lett. 2009, 19, 1357 - 1360
165. Mitsuya, M.; Kamata, K.; Bamba, M.; Watanabe, H.; Sasaki, Y.; Sasaki, K.; Ohyama, S.; Hosaka, H.; Nagata, Y.; Eiki, J.-i.; Nishimura, T. Discovery of novel 3,6-disubstituted 2-pyridinecarboxamide derivatives as GK activators Bioorg. Med. Chem. Lett. 2009, 19, 2718 - 2712
166. Bode, C. M.; Boezio, A. A.; Albrecht, B. K.; Bellon, S. F.; Berry, L.; Broome, M. A.; Choquette, D.; Dussault, I.; Lewis, R. T.; Lin, M.-H. J.; Rex, K.; Whittington, D. A.; Yang, Y.; Harmange, J.-C. Discovery and optimization of a potent and selective triazolopyridinone series of c-Met inhibitors Bioorg. Med. Chem. Lett. 2012, 22, 4089 - 4093
167. Albrecht, B. K.; Harmange, J.-C.; Bauer, D.; Berry, L.; Bode, C.; Boezio, A. A.; Chen, A.; Choquette, D.; Dussault, I.; Fridrich, C.; Hirai, S.; Hoffman, D.; Larrow, J. F.; Kaplan-Lefko, P.; Lin, J.; Lohman, J.; Long, A. M.; Moriguchi, J.; O'Connor, A.; Potashman, M. H.; Reese, M.; Rex, K.; Siegmund, A.; Shah, K.; Shimanovich, R.; Springer, S. K.; Teffera, Y.; Yang, Y.; Zhang, Y.; Bellon, S. F. Discovery and optimization of triazolopyridazines as potent and selective inhibitors of the c-Met kinase J. Med. Chem. 2008, 51, 2879 - 2882
168. Boezio, A. A.; Berry, L.; Albrecht, B. K.; Bauer, D.; Bellon, S. F.; Bode, C.; Chen, A.; Choquette, D.; Dussault, I.; Hirai, S.; Kaplan-Lefko, P.; Larrow, J. F.; Lin, M.-H. J.; Lohman, J.; Potashman, M. H.; Rex, K.; Santostefano, M.; Shah, K.; Shimanovich, R.; Springer, S. K.; Teffera, Y.; Yang, Y.; Zhang, Y.; Harmange, J. C. Discovery and optimization of potent and selective triazolopyridazine series of c-Met inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 6307 - 6312
169. Flygare, J. A.; Beresini, M.; Budha, N.; Chan, H.; Chan, I. T.; Cheeti, S.; Cohen, F.; Deshayes, K.; Doerner, K.; Eckhardt, S. G.; Elliott, L. O.; Feng, B.; Franklin, M. C.; Frankovitz Reisner, S.; Gazzard, L.; Halladay, J.; Hymowitz, S. G.; La, H.; LoRusso, P.; Maurer, B.; Murray, L.; Plise, E.; Quan, C.; Stephan, J.-P.; Young, S. G.; Tom, J.; Tsui, V.; Um, J.; Varfolomeev, E.; Vucic, D.; Wagner, A. J.; Wallweber, H. J. A.; Wang, L.; Ware, J.; Wen, Z.; Wong, H.; Wong, J. M.; Wong, M.; Wong, S.; Yu, R.; Zobel, K.; Fairbrother, W. J. Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152) J. Med. Chem. 2012, 55, 4101 - 4113
170. Bartlett, G. J.; Choudhary, A.; Raines, R. T.; Woolfson, D. N. n→π∗ Interactions in proteins Nature Chem. Biol. 2010, 6, 615 - 620
171. Newberry, R. W.; Van Veller, B.; Guzei, I. A.; Raines, R. T. n→π∗ Interactions of amides and thioamides: implications for protein stability J. Am. Chem. Soc. 2013, 135, 7843 - 7846
172. Hodges, J. A.; Raines, R. T. Energetics of an n→π∗ interaction that impacts protein structure Org. Lett. 2006, 8, 4695 - 4697
173. Choudhoury, A.; Gandla, D.; Krow, G. R.; Raines, R. T. Nature of amide carbonyl-carbonyl interactions in proteins J. Am. Chem. Soc. 2009, 131, 7244 - 7246
174. Nagao, Y.; Honjo, T.; Iimori, H.; Goto, S.; Sano, S.; Shiro, M.; Yamaguchi, K.; Sei, Y. Intramolecular nonbonded S···O interaction in acetazolamide and thiadiazolinethione molecules in their dimeric crystalline structures and complex crystalline structures with enzymes Tetrahedron Lett. 2004, 45, 8757 - 8761
175. Honda, T.; Tajima, H.; Kaneko, Y.; Ban, M.; Inaba, T.; Takeno, Y.; Okamoto, K.; Aono, H. Conformation-activity relationship on novel 4-pyridylmethylthio derivatives with antiangiogenic activity Bioorg. Med. Chem. Lett. 2008, 18, 2939 - 2943
176. Tajima, H.; Honda, T.; Kawashima, K.; Sasabuchi, Y.; Yamamoto, M.; Ban, M.; Okamoto, K.; Inoue, K.; Inaba, T.; Takeno, Y.; Aono, H. Pyridylmethylthio derivatives as VEGF inhibitors. Part 1 Bioorg. Med. Chem. Lett. 2010, 20, 7234 - 7238
177. Tajima, H.; Honda, T.; Kawashima, K.; Sasabuchi, Y.; Yamamoto, M.; Ban, M.; Okamoto, K.; Inoue, K.; Inaba, T.; Takeno, Y.; Tsuboi, T.; Tonouchi, A.; Aono, H. Pyridylmethylthio derivatives as VEGF inhibitors. Part 2 Bioorg. Med. Chem. Lett. 2011, 21, 1232 - 1235
178. Suzuki, T.; Imai, K.; Nakagawa, H.; Miyata, N. 2-Anilinobenzamides as SIRT inhibitors ChemMedChem 2006, 1, 1059 - 1062
179. Suzuki, T.; Imai, K.; Imai, E.; Iida, S.; Ueda, R.; Tsumoto, H.; Nakagawa, H.; Miyata, N. Design, synthesis, enzyme inhibition, and tumor cell growth inhibition of 2-anilinobenzamide derivatives as SIRT1 inhibitors Bioorg. Med. Chem. 2009, 17, 5900 - 5905
180. Tomoo, T.; Nakatsuka, T.; Katayama, T.; Hayashi, Y.; Fujieda, Y.; Terakawa, M.; Nagahira, K. Design, synthesis and biological evaluation of 2-(1-aryl-1 H -indol-5-yl)propanoic acids as new indole-based cytosolic phospholipase A2α inhibitors J. Med. Chem. 2014, 57, 7244 - 7262
181. Hornberger, K. R.; Chen, X.; Crew, A. P.; Kleinberg, A.; Ma, L.; Mulvihill, M. J.; Wang, J.; Wilde, V. L.; Albertella, M.; Bittner, M.; Cooke, A.; Kadhim, S.; Kahler, J.; Maresca, P.; May, E.; Meyn, P.; Romashko, D.; Tokar, B.; Turton, R. Discovery of 7-aminofuro[2,3- c ]pyridine inhibitors of TAK1: optimization of kinase selectivity and pharmacokinetics Bioorg. Med. Chem. Lett. 2013, 23, 4511 - 4516
182. Hornberger, K. R.; Berger, D. M.; Crew, A. P.; Dong, H.; Kleinberg, A.; Li, A.-H.; Medeiros, M. R.; Mulvihill, M. J.; Siu, K.; Tarrant, J.; Wang, J.; Weng, F.; Wilde, V. L.; Albertella, M.; Bittner, M.; Cooke, A.; Gray, M. J.; Maresca, P.; May, E.; Meyn, P.; Peick, W., Jr.; Romashko, D.; Tanowitz, M.; Tokar, B. Discovery and optimization of 7-aminofuro[2,3-c]pyridine inhibitors of TAK1 Bioorg. Med. Chem. Lett. 2013, 23, 4517 - 4522
183. Honda, T.; Terao, T.; Aono, H.; Ban, M. Synthesis of novel 1,4-benzoxazin-3-one derivatives as inhibitors against tyrosine kinases Bioorg. Med. Chem. 2009, 17, 699 - 708
184. Birman, V. B.; Li, X.; Han, Z. Nonaromatic amidine derivatives as acylation catalysts Org. Lett. 2007, 9, 37 - 40
185. Kobayashi, M.; Okamoto, S. Unexpected reactivity of annulated 3 H -benzothiazol-2-ylideneamines as an acyl transfer catalyst Tetrahedron Lett. 2006, 47, 4347 - 4350
186. Birman, V. B.; Li, X. Benzotetramisole: a remarkably enantioselective acyl transfer catalyst Org. Lett. 2006, 8, 1351 - 1354
187. Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. Kinetic resolution of 2-oxazoldinones via catalytic, enantioselective N-acylation J. Am. Chem. Soc. 2006, 128, 6536 - 6537
188. Birman, V. B.; Guo, L. Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole Org. Lett. 2006, 8, 4859 - 4861
189. Birman, V. B.; Jiang, H.; Li, X. Enantioselective synthesis of lobeline via nonenzymatic desymmetrization Org. Lett. 2007, 9, 3237 - 3240
190. Birman, V. B.; Li, X. Homobenzotetramisole: an effective catalyst for kinetic resolution of aryl-cycloalkanols Org. Lett. 2008, 10, 1115 - 1118
191. Yang, X.; Lu, G.; Birman, V. B. Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones Org. Lett. 2010, 12, 892 - 895
192. Shiina, I.; Nakata, K.; Ono, K.; Onda, Y.; Itagaki, M. Kinetic resolution of racemic α-arylalkanoic acids with achiral alcohols via the asymmetric esterification using carboxylic anhydrides and acyl-transfer catalysts J. Am. Chem. Soc. 2010, 132, 11629 - 11641
193. Leverett, C. A.; Purohit, V. C.; Romo, D. Enantioselective, organocatalyzed, intramolecular aldol lactonizations with keto acids leading to bi- and tricyclic β-lactones and topology-morphing transformations Angew. Chem., Int. Ed. 2010, 49, 9479 - 9483
194. Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M. Z.; Smith, A. D. Organocatalytic functionalization of carboxylic acids: isothiourea-catalyzed asymmetric intra- and intermolecular Michael addition-lactonizations J. Am. Chem. Soc. 2011, 133, 2714 - 2720
195. Morrill, L. C.; Stark, D. G.; Taylor, J. E.; Smith, S. R.; Squires, J. A.; D'Hollander, A. C. A.; Simal, C.; Shapland, P.; O'Riordan, T. J. C.; Smith, A. D. Organocatalytic Michael addition-lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents Org. Biomol. Chem. 2014, 12, 9016 - 9027
196. Salimbeni, A.; Canevotti, R.; Paleari, F.; Poma, D.; Caliari, S.; Fici, F.; Cirillo, R.; Renzetti, A. R.; Subissi, A.; Belvisi, L.; Bravi, G.; Scolastico, C.; Giachetti, A. N-3-Substituted pyrimidinones as potent, orally active, AT1 selective angiotensin II receptor antagonists J. Med. Chem. 1995, 38, 4806 - 4820
197. Destro, R.; Soave, R. A new non-peptide angiotensin II receptor antagonist Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, 51, 1383 - 1385
198. Destro, R.; Soave, R.; Barzaghi, M.; Lo Presti, L. Progress in understanding of drug-receptor interactions, Part 1: experimental charge-density study of an angiotensin II receptor antagonist (C30H30N6O3S) at T = 17 K Chem.-Eur. J. 2005, 11, 4621 - 4634
199. Soave, R.; Barzaghi, M.; Destro, R. Progress in understanding of drug-receptor interactions, part 2: experimental and theoretical electrostatic moments and interaction energies of an angiotensin II receptor antagonist (C30H30N6O3S) Chem.-Eur. J. 2007, 13, 6942 - 6956
200. Sugiyama, H.; Yoshida, M.; Mori, K.; Kawamoto, T.; Sogabe, S.; Takagi, T.; Oki, H.; Tanaka, T.; Kimura, H.; Ikeura, Y. Synthesis and structure-activity relationship studies of benzothieno[3,2-b]furan derivatives as a novel class of IKKβ inhibitors Chem. Pharm. Bull. 2007, 55, 613 - 624
201. McInerney, B. V.; Gregson, R. P.; Lacey, M. J.; Akhurst, R. J.; Lyons, G. R.; Rhodes, S. H.; Smith, D. R. J.; Engelhardt, L. M.; White, A. H. Biologically active metabolites from Xenorhabdus spp. Part 1. Dithiolopyrrolone derivatives with antibiotic activity J. Nat. Products 1991, 54, 774 - 784
202. Burling, F. T.; Goldstein, B. M. A database study of nonbonded intramolecular sulfur-nucleophile contacts Acta Crystallogr., Part B: Struct. Sci. 1993, B49, 738 - 744
203. Huber, C. P.; Carey, P. R.; Hsi, S.-C.; Lee, H.; Storer, A. C. Conformational study of N -acyl amino acid esters and thiol esters by FT-IR and X-ray crystallography: evidence for a N···S interaction in thiol esters J. Am. Chem. Soc. 1984, 106, 8263 - 8268
204. Varughese, K. I.; Storer, A. C.; Carey, P. R. Directional preference for a catalytically important N-S contact seen in acyl-thiolproteases J. Am. Chem. Soc. 1984, 106, 8252 - 8257
205. Carey, P. R.; Lee, H.; Ozaki, Y.; Storer, A. C. Rate-structure correlation for enzyme-substrate intermediates: resonance Raman and kinetic studies on some N -benzoylglycine (dithioacyl)papains J. Am. Chem. Soc. 1984, 106, 8258 - 8262
206. Carey, P. R.; Storer, A. C. Molecular details of enzyme-substrate transients by resonance Raman spectroscopy Acc. Chem. Res. 1983, 16, 455 - 460
207. Hayashi, K.; Ogawa, S.; Sano, S.; Shiro, M.; Yamaguchi, K.; Sei, Y.; Nagao, Y. Intramolecular nonbonded S···N interaction in rabeprazole Chem. Pharm. Bull. 2008, 56, 802 - 806
208. Kuti, M.; Rátbai, J.; Kapovits, I.; Kucsman, A.; Párkányi, L.; Argay, Gy.; Kálmán, A. Transannular sulfur-nitrogen interaction in 1,5-thiazonine derivatives: an X-ray study J. Mol. Struct. 1994, 318, 161 - 169
209. Kuti, M.; Rátbai, J.; Kapovits, I.; Jalsovszky, I.; Argay, Gy.; Kálmán, A.; Párkányi, L. Transannular sulfur-nitrogen interaction in 1,5-thiazocine derivatives: an X-ray study J. Mol. Struct. 1996, 382, 1 - 11
210. Fukumoto, S.; Nakashima, T.; Kawai, T. Photon-quantitative reaction of a dithiazolylarylene in solution Angew. Chem., Int. Ed. 2011, 50, 1565 - 1568
211. Rheault, T. R.; Stellwagen, J. C.; Adjabeng, G. M.; Hornberger, K. R.; Petrov, K. G.; Waterson, A. G.; Dickerson, S. H.; Mook, R. A., Jr.; Laquerre, S. G.; King, A. J.; Rossanese, O. W.; Arnone, M. R.; Smitheman, K. N.; Kane-Carson, L. S.; Han, C.; Moorthy, G. S.; Moss, K. G.; Uehling, D. E. Discovery of dabrafenib: a selective inhibitor of Raf kinases with antitumor activity against B-Raf-driven tumors ACS Med. Chem. Lett. 2013, 4, 358 - 362
212. Haack, T.; Fattori, R.; Napoletano, M.; Pellacini, F.; Fronza, G.; Raffainic, G.; Ganazzolic, F. Phthalazine PDE IV inhibitors: conformational study of some 6-methoxy-1,4-disubstituted derivatives Bioorg. Med. Chem. 2005, 13, 4425 - 4433
213. Cummings, M. D.; Lindberg, J.; Lin, T.-I.; de Kock, H.; Lenz, O.; Lilja, E.; Felländer, S.; Baraznenok, V.; Nyström, S.; Nilsson, M.; Vrang, L.; Edlund, M.; Rosenquist, Å.; Samuelsson, B.; Raboisson, P.; Simmen, K. Induced-fit binding of the macrocyclic noncovalent inhibitor TMS435 to its HCV NS3/NS4A protease target Angew. Chem., Int. Ed. 2010, 49, 1652 - 1655
214. Kazmierski, W. M.; Hamatake, R.; Duan, M.; Wright, L. L.; Smith, G. K.; Jarvest, R. L.; Ji, J.-J.; Cooper, J. P.; Tallant, M. D.; Crosby, R. M.; Creech, K.; Wang, A.; Li, X.; Zhang, S.; Zhang, Y.-K.; Liu, Y.; Ding, C. Z.; Zhou, Y.; Plattner, J. J.; Baker, S. J.; Bu, W.; Liu, L. Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants J. Med. Chem. 2012, 55, 3021 - 3026
215. Maloney, K. N.; MacMillan, J. B.; Kauffman, C. A.; Jensen, P. R.; DiPasquale, A. G.; Rheingold, A. L.; Fenical, W. Lodopyridone, a structurally unprecedented alkaloid from a marine actinomycete Org. Lett. 2009, 11, 5422 - 5424
216. George, I. R.; Lewis, W.; Moody, C. J. Synthesis of lodopyridone Tetrahedron 2013, 69, 8209 - 8215
217. da Silva, L. E.; Joussef, A. C.; Forob, S.; Schmidt, B. 2-(1,3-Benzothiazol-2-yl)quinolin-8-ol Acta Crystallogr., Sect. E: Struct. Rep. Online 2006, E62, o880 - o881
218. Arnison, P. G.; Bibb, M. J.; Bierbaum, G.; Bowers, A. A.; Bugni, T. S.; Bulaj, G.; Camarero, J. A.; Campopiano, D.; Challis, J. G. L.; Clardy, J.; Cotter, P. D.; Craik, D. J.; Dawson, M.; Dittmann, E.; Donadio, S.; Dorrestein, P. C.; Entian, K.-D.; Fischbach, M. A.; Garavelli, J. S.; Goransson, U.; Gruber, C. W.; Haft, D. H.; Hemscheidt, T. K.; Hertweck, C.; Hill, C.; Horswill, A. R.; Jaspars, M.; Kelly, W. L.; Klinman, J. P.; Kuipers, O. P.; Link, A. J.; Liu, W.; Marahiel, M. A.; Mitchell, D. A.; Moll, G. N.; Moore, B. S.; Muller, R.; Nair, S. K.; Nes, I. F.; Norris, G. E.; Olivera, B. M.; Onaka, H.; Patchett, M. L.; Piel, J.; Reaney, M. J. T.; Rebuffat, S.; Ross, R. P.; Sahl, H.-G.; Schmidt, E. W.; Selsted, M. E.; Severinov, K.; Shen, B.; Sivonen, K.; Smith, L.; Stein, T.; Süssmuth, R. D.; Tagg, J. R.; Tang, G.-L.; Truman, A. W.; Vederas, J. C.; Walsh, C. T.; Walton, J. D.; Wenzel, S. C.; Willey, J. M.; van der Donk, W. A. Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature Nat. Prod. Rep. 2013, 30, 108 - 160
219. James, M. N. G.; Watson, K. J. Chemistry of micrococcin P. Part IX. The crystal and molecular structure of micrococcinic acid bis-4-bromoanilide J. Chem. Soc. C 1966, 1361 - 1371
220. Iwaki, Y.; Yamamura, S.; Akita, H. Asymmetric syntheses and structure elucidation of cystothiazole A metabolites of the myxobacterium Cystobacter fuscus Tetrahedron: Asymmetry 2008, 19, 2192 - 2200
221. Naumov, P.; Ozawa, Y.; Ohkubo, K.; Fukuzumi, S. Structure and spectroscopy of oxyluciferin, the light emitter of the firefly bioluminescence J. Am. Chem. Soc. 2009, 131, 11590 - 11605
222. Maltsev, O. V.; Nath, N. K.; Naumov, P.; Hintermann, L. Why is firefly oxyluciferin a notoriously labile substance Angew. Chem., Int. Ed. 2014, 53, 847 - 850
223. Yoo, C. L.; Yu, G. J.; Yang, B.; Robins, L. I.; Verkmanb, A. S.; Kurth, M. J. 4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing Bioorg. Med. Chem. Lett. 2008, 18, 2610 - 2614
224. Coffman, K. C.; Nguyen, H. H.; Phuan, P.-W.; Hudson, B. M.; Yu, G.; Bagdazarian, A. L.; Montgomery, D.; Lodewyk, M. W.; Yang, B.; Yoo, C. L.; Verkman, A. S.; Tantillo, D. J.; Kurth, M. J. Constrained bithiazoles: small molecule correctors of defective ΔF508-CFTR protein trafficking J. Med. Chem. 2014, 57, 6729 - 6738
225. Ye, L.; Hu, B.; El-Badri, F.; Hudson, B. M.; Phuan, P.-W.; Verkman, A. S.; Tantillo, D. J.; Kurth, M. J. ΔF508-CFTR correctors: synthesis and evaluation of thiazole-tethered imidazolones, oxazoles, oxadiazoles, and thiadiazoles Bioorg. Med. Chem. Lett. 2014, 24, 5840 - 5844
226. Vogt, D.; Weber, J.; Ihlefeld, K.; Brüggerhoff, A.; Proschak, E.; Stark, H. Design, synthesis and evaluation of 2-aminothiazole derivatives as sphingosine kinase inhibitors Bioorg. Med. Chem. 2014, 22, 5354 - 5367
227. Oka, Y.; Yabuuchi, T.; Fujii, Y.; Ohtake, H.; Wakahara, S.; Matsumoto, K.; Endo, M.; Tamura, Y.; Sekiguchi, Y. Discovery and optimization of a series of 2-aminothiazole-oxazoles as potent phosphoinositide 3-kinase γ inhibitors Bioorg. Med. Chem. Lett. 2012, 22, 7534 - 7538
228. Oka, Y.; Yabuuchi, T.; Oi, T.; Kuroda, S.; Fujii, Y.; Ohtake, H.; Inoue, T.; Wakahara, S.; Kimura, K.; Fujita, K.; Endo, M.; Taguchi, K.; Sekiguchi, Y. Discovery of N -{5-[3-(3-hydroxypiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-4-methyl-1,3-thiazol-2-yl}acetamide (TASP0415914) as an orally potent phosphoinositide 3-kinase γ inhibitor for the treatment of inflammatory diseases Bioorg. Med. Chem. 2013, 21, 7578 - 7583
229. Flipo, M.; Desroses, M.; Lecat-Guillet, N.; Dirié, B.; Carette, X.; Leroux, F.; Piveteau, C.; Demirkaya, F.; Lens, Z.; Rucktooa, P.; Villeret, V.; Christophe, T.; Jeon, H. K.; Locht, C.; Brodin, P.; Déprez, B.; Baulard, A. R.; Willand, N. Ethionamide boosters: synthesis, biological activity, and structure-activity relationships of a series of 1,2,4-oxadiazole EthR inhibitors J. Med. Chem. 2011, 54, 2994 - 3010
230. Flipo, M.; Desroses, M.; Lecat-Guillet, N.; Villemagne, B.; Blondiaux, N.; Leroux, F.; Piveteau, C.; Mathys, V.; Flament, M.-P.; Siepmann, J.; Villeret, V.; Wohlkönig, A.; Wintjens, R.; Soror, S. H.; Christophe, T.; Jeon, H. K.; Locht, C.; Brodin, P.; Déprez, B.; Baulard, A. R.; Willand, N. Ethionamide boosters. 2. Combining bioisosteric replacement and structure-based drug design to solve pharmacokinetic issues in a series of potent 1,2,4-oxadiazole EthR inhibitors J. Med. Chem. 2012, 55, 68 - 83
231. Lee, S. W.; Mitchell, D. A.; Markley, A. L.; Hensler, M. E.; Gonzalez, D.; Wohlrab, A.; Dorrestein, P. C.; Nizet, V.; Dixon, J. E. Discovery of a widely distributed toxin biosynthetic gene cluster Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 5879 - 5884
232. Kalyon, B.; Helaly, S. E.; Scholz, R.; Nachtigall, J.; Vater, J.; Borriss, R.; Süssmuth, R. D. Plantazolicin A and B: Structure elucidation of ribosomally synthesized thiazole/oxazole peptides from Bacillus amyloliquefaciens FZB42 Org. Lett. 2011, 13, 2996 - 2999
233. Molohon, K. J.; Melby, J. O.; Lee, J.; Evans, B. S.; Dunbar, K. L.; Bumpus, S. B.; Kelleher, N. L.; Mitchell, D. A. Structure determination and interception of biosynthetic intermediates for the plantazolicin class of highly discriminating antibiotics ACS Chem. Biol. 2011, 6, 1307 - 1313
234. Sharma, A.; Blair, P. M.; Mitchell, D. A. Synthesis of plantazolicin analogues enables dissection of ligand binding interactions of a highly selective methyltransferase Org. Lett. 2013, 15, 5076 - 5079
235. Atobe, M.; Naganuma, K.; Kawanishi, M.; Morimoto, A.; Kasahara, K.-i.; Ohashi, S.; Suzuki, H.; Hayashi, T.; Miyoshi, S. SAR-based optimization of 2-(1 H-pyrazol-1-yl)-thiazole derivatives as highly potent EP1 receptor antagonists Bioorg. Med. Chem. Lett. 2013, 23, 6569 - 6576
236. Atobe, M.; Naganuma, K.; Kawanishi, M.; Morimoto, A.; Kasahara, K.-i.; Ohashi, S.; Suzuki, H.; Hayashi, T.; Miyoshi, S. Hit-to-lead optimization of 2-(1 H-pyrazol-1-yl)-thiazole derivatives as a novel class of EP1 receptor antagonists Bioorg. Med. Chem. Lett. 2013, 23, 6064 - 6067
237. Ronkin, S. M.; Badia, M.; Bellon, S.; Grillot, A.-L.; Gross, C. H.; Grossman, T. H.; Mani, N.; Parsons, J. D.; Stamos, D.; Trudeau, M.; Wei, Y.; Charifson, P. S. Discovery of pyrazolothiazoles as novel and potent inhibitors of bacterial gyrase Bioorg. Med. Chem. Lett. 2010, 20, 2828 - 2831
238. Lam, T.; Hilgers, M. T.; Cunningham, M. L.; Kwan, B. P.; Nelson, K. J.; Brown-Driver, V.; Ong, V.; Trzoss, M.; Hough, G.; Shaw, K. J.; Finn, J. Structure-based design of new dihydrofolate reductase antibacterial agents: 7-(benzimidazol-1-yl)-2,4-diaminoquinazolines J. Med. Chem. 2014, 57, 651 - 668
239. Zampese, J. A.; Keene, F. R.; Steel, P. J. Diastereoisomeric dinuclear ruthenium complexes of 2,5-di(2-pyridyl)thiazolo[5,4-d]thiazole Dalton Trans. 2004, 4124 - 4129
240. Knighton, R. C.; Hallett, A. J.; Kariuki, B. M.; Pope, S. J. A. A one-step synthesis towards new ligands based on aryl-functionalised thiazolo[5,4-d]thiazole chromophores Tetrahedron Lett. 2010, 51, 5419 - 5422
241. Naraso; Wudl, F. Two poly(2,5-thienythiazolothiazole)s: observation of spontaneous ordering in thin films Macromolecules 2008, 41, 3169 - 3174
242. Wang, C.; Han, Y.; Wu, A.; Sólyom, S.; Niu, L. Mechanism and site of inhibition of AMPA receptors: pairing a thiadiazole with a 2,3-benzodiazepine scaffold ACS Chem. Neurosci. 2014, 5, 138 - 147
243. Shultz, M. D.; Kirby, C. A.; Stams, T.; Chin, D. N.; Blank, J.; Charlat, O.; Cheng, H.; Cheung, A.; Cong, F.; Feng, Y.; Fortin, P. D.; Hood, T.; Tyagi, V.; Xu, M.; Zhang, B.; Shao, W. [1,2,4]Triazol-3-ylsulfanylmethyl)-3-phenyl-[1,2,4]oxadiazoles: antagonists of the Wnt pathway that inhibit tankyrases 1 and 2 via novel adenosine pocket binding J. Med. Chem. 2012, 55, 1127 - 1136
244. Bilodeau, M. T.; Rodman, L. D.; McGaughey, G. B.; Coll, K. E.; Koester, T. J.; Hoffman, W. F.; Hungate, R. W.; Kendall, R. L.; McFall, R. C.; Rickert, K. W.; Rutledge, R. Z.; Thomas, K. A. The discovery of N -(1,3-thiazol-2-yl)pyridin-2-amines as potent inhibitors of KDR kinase Bioorg. Med. Chem. Lett. 2004, 14, 2941 - 2945
245. Bilodeau, M. T.; Balitza, A. E.; Koester, T. J.; Manley, P. J.; Rodman, L. D.; Buser-Doepner, C.; Coll, K. E.; Fernandes, C.; Gibbs, J. B.; Heimbrook, D. C.; Huckle, W. R.; Kohl, N.; Lynch, J. J.; Mao, X.; McFall, R. C.; McLoughlin, D.; Miller-Stein, C. M.; Rickert, K. W.; Sepp-Lorenzino, L.; Shipman, J. M.; Subramanian, R.; Thomas, K. A.; Wong, B. K.; Yu, S.; Hartman, G. D. Potent N-(1,3-thiazol-2-yl)pyridin-2-amine vascular endothelial growth factor receptor tyrosine kinase inhibitors with excellent pharmacokinetics and low affinity for the hERG ion channel J. Med. Chem. 2004, 47, 6363 - 6372
246. Das, J.; Moquin, R. V.; Lin, J.; Liu, C.; Doweyko, A. M.; DeFex, H. F.; Fang, Q.; Pang, S.; Pitt, S.; Shen, D. R.; Schieven, G. L.; Barrish, J. C.; Wityak, J. Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors Bioorg. Med. Chem. Lett. 2003, 13, 2587 - 2590
247. Dudkin, V. Y.; Rickert, K.; Kreatsoulas, C.; Wang, C.; Arrington, K. L.; Fraley, M. E.; Hartman, G. D.; Yan, Y.; Ikuta, M.; Stirdivant, S. M.; Drakas, R. A.; Walsh, E. S.; Hamilton, K.; Buser, C. A.; Lobell, R. B.; Sepp-Lorenzino, L. Pyridyl aminothiazoles as potent inhibitors of Chk1 with slow dissociation rates Bioorg. Med. Chem. Lett. 2012, 22, 2609 - 2612
248. Dudkin, V. Y.; Wang, C.; Arrington, K. L.; Fraley, M. E.; Hartman, G. D.; Stirdivant, S. M.; Drakas, R. A.; Rickert, K.; Walsh, E. S.; Hamilton, K.; Buser, C. A.; Hardwick, J.; Tao, W.; Beck, S. C.; Mao, X.; Lobell, R. B.; Sepp-Lorenzino, L. Pyridyl aminothiazoles as potent Chk1 inhibitors: optimization of cellular activity Bioorg. Med. Chem. Lett. 2012, 22, 2613 - 2619
249. Haidle, A. M.; Zabierek, A. A.; Childers, K. K.; Rosenstein, C.; Mathur, A.; Altman, M. D.; Chan, G.; Xu, L.; Bachman, E.; Mo, J.-R.; Bouthillette, M.; Rush, T.; Tempesta, P.; Marshall, C. G.; Young, J. R. Thiophene carboxamide inhibitors of JAK2 as potential treatments for myleoproliferative neoplasms Bioorg. Med. Chem. Lett. 2014, 24, 1968 - 1973
250. Hinklin, R. J.; Boyd, S. A.; Chicarelli, M. J.; Condroski, K. R.; DeWolf, W. E., Jr.; Lee, P. A.; Lee, W.; Singh, A.; Thomas, L.; Voegtli, W. C.; Williams, L.; Aicher, T. D. Identification of a new class of glucokinase activators through structure-based design J. Med. Chem. 2013, 56, 7669 - 7678
251. Waring, M. J.; Johnstone, C.; McKerrecher, D.; Pike, K. G.; Robb, G. Matrix-based multiparameter optimization of glucokinase activators: the discovery of AZD1092 Med. Chem. Commun. 2011, 2, 775 - 779
252. Hinklin, R. J.; Aicher, T. D.; Anderson, D. A.; Baer, B. R.; Boyd, S. A.; Condroski, K. R.; DeWolf, W. E., Jr.; Kraser, C. F.; McVean, M.; Rhodes, S. P.; Sturgis, H. L.; Voegtli, W. C.; Williams, L.; Houze, J. B. Discovery of 2-pyridylureas as glucokinase activators J. Med. Chem. 2014, 57, 8180 - 8186
253. Shirude, P. S.; Madhavapeddi, P.; Naik, M.; Murugan, K.; Shinde, V.; Nandishaiah, R.; Bhat, J.; Kumar, A.; Hameed, S.; Holdgate, G.; Davies, G.; McMiken, H.; Hegde, N.; Ambady, A.; Venkatraman, J.; Panda, M.; Bandodkar, B.; Sambandamurthy, V. K.; Read, J. A. Methyl-thiazoles: a novel mode of inhibition with the potential to develop novel inhibitors targeting InhA in Mycobacterium tuberculosis J. Med. Chem. 2013, 56, 8533 - 8542
254. Shimamura, T.; Shibata, J.; Kurihara, H.; Mita, T.; Otsuki, S.; Sagara, T.; Hirai, H.; Iwasawa, Y. Identification of potent 5-pyrimidinyl-2-aminothiazole CDK4, 6 inhibitors with significant selectivity over CDK1, 2, 5, 7, and 9 Bioorg. Med. Chem. Lett. 2006, 16, 3751 - 3754
255. Ghaemmaghami, S.; Russo, M.; Renslo, A. R. Successes and challenges in phenotype-based lead discovery for prion diseases J. Med. Chem. 2014, 57, 6919 - 6929
256. Gallardo-Godoy, A.; Gever, J.; Fife, K. L.; Silber, B. M.; Prusiner, S. B.; Renslo, A. R. 2-Aminothiazoles as therapeutic leads for prion diseases J. Med. Chem. 2011, 54, 1010 - 1021
257. Silber, B. M.; Rao, S.; Fife, K. L.; Gallardo-Godoy, A.; Renslo, A. R.; Dalvie, D. K.; Giles, K.; Freyman, Y.; Elepano, M.; Gever, J. R.; Li, Z.; Jacobson, M. P.; Huang, Y.; Benet, L. Z.; Prusiner, S. B. Pharmacokinetics and metabolism of 2-aminothiazoles with antiprion activity in mice Pharm. Res. 2013, 30, 932 - 950
258. Li, Z.; Silber, B. M.; Rao, S.; Gever, J. R.; Bryant, C.; Gallardo-Godoy, A.; Dolghih, E.; Widjaja, K.; Elepano, M.; Jacobson, M. P.; Prusiner, S. B.; Renslo, A. R. 2-Aminothiazoles with improved pharmacotherapeutic properties for treatment of prion disease ChemMedChem 2013, 8, 847 - 857
259. Ioannidis, S.; Lamb, M. L.; Almeida, L.; Guan, H.; Peng, B.; Bebernitz, G.; Bell, K.; Alimzhanov, M.; Zinda, M. Replacement of pyrazol-3-yl amine hinge binder with thiazol-2-yl amine: Discovery of potent and selective JAK2 inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 1669 - 1673
260. Guan, H.; Lamb, M. L.; Peng, B.; Huang, S.; DeGrace, N.; Read, J.; Hussain, S.; Wu, J.; Rivard, C.; Alimzhanov, M.; Bebernitz, G.; Bell, K.; Ye, M.; Zinda, M.; Ioannidis, S. Discovery of novel JAK2-STAT pathway inhibitors with extended residence time on target Bioorg. Med. Chem. Lett. 2013, 23, 3105 - 3110
261. Dietchfield, C.; Johnson, V. L.; Tighe, A.; Ellston, R.; Haworth, C.; Johnson, T.; Mortlock, A.; Keen, N.; Taylor, S. S. Aurora B couples chromosome alignment with anaphase by targeting BubR1, Mad2, and Cenp-E to kinetochores J. Cell. Biol. 2003, 161, 267 - 280
262. Jung, F. H.; Pasquet, G.; Lambert-van der Brempt, C.; Lohmann, J.-J. M.; Warin, N.; Renaud, F.; Germain, H.; De Savi, C.; Roberts, N.; Johnson, T.; Dousson, C.; Hill, G. B.; Mortlock, A. A.; Heron, N.; Wilkinson, R. W.; Wedge, S. R.; Heaton, S. P.; Odedra, R.; Keen, N. J.; Green, S.; Brown, E.; Thompson, K.; Brightwell, S. Discovery of novel and potent thiazoloquinazolines as selective aurora A and B kinase inhibitors J. Med. Chem. 2006, 49, 955 - 970
263. Belanger, D. B.; Curran, P. J.; Hruza, A.; Voigt, J.; Meng, Z.; Mandal, A. K.; Siddiqui, M. A.; Basso, A. D.; Gray, K. Discovery of imidazo[1,2-a]pyrazine-based Aurora kinase inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 5170 - 5174
264. Meng, Z.; Kulkarni, B. A.; Kerekes, A. D.; Mandal, A. K.; Esposite, S. J.; Belanger, D. B.; Reddy, P. A.; Basso, A. D.; Tevar, S.; Gray, K.; Jones, J.; Smith, E. B.; Doll, R. J.; Siddiqui, M. A. Bioisosteric approach to the discovery of imidazo[1,2-a]pyrazines as potent Aurora kinase inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 592 - 598
265. Belanger, D. B.; Williams, M. J.; Curran, P. J.; Mandal, A. K.; Meng, Z.; Rainka, M. P.; Yu, T.; Shih, N.-Y.; Siddiqui, M. A.; Liu, M.; Tevar, S.; Lee, S.; Liang, L.; Gray, K.; Yaremko, B.; Jones, J.; Smith, E. B.; Prelusky, D. B.; Basso, A. D. Discovery of orally bioavailable imidazo[1,2-a]pyrazine-based Aurora kinase inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 6739 - 6743
266. Yu, T.; Tagat, J. R.; Kerekes, A. D.; Doll, R. J.; Zhang, Y.; Xiao, Y.; Esposite, S.; Belanger, D. B.; Curran, P. J.; Mandal, A. K.; Siddiqui, M. A.; Shih, N.-Y.; Basso, A. D.; Liu, M.; Gray, K.; Tevar, S.; Jones, J.; Lee, S.; Liang, L.; Ponery, S.; Smith, E. B.; Hruza, A.; Voigt, J.; Ramanathan, L.; Prosise, W.; Hu, M. Discovery of a potent, injectable inhibitor of aurora kinases based on the imidazo-[1,2-a]-pyrazine core ACS Med. Chem. Lett. 2010, 1, 214 - 218
267. Kerekes, A. D.; Esposite, S. J.; Doll, R. J.; Tagat, J. R.; Yu, T.; Xiao, Y.; Zhang, Y.; Prelusky, D. B.; Tevar, S.; Gray, K.; Terracina, G. A.; Lee, S.; Jones, J.; Liu, M.; Basso, A. D.; Smith, E. B. Aurora kinase inhibitors based on the imidazo[1,2-a]pyrazine core: fluorine and deuterium incorporation improve oral absorption and exposure J. Med. Chem. 2011, 54, 201 - 210
268. Reker, D.; Seet, M.; Pillong, M.; Koch, C. P.; Schneider, P.; Witschel, M. C.; Rottmann, M.; Freymond, C.; Brun, R.; Schweizer, B.; Illarionov, B.; Bacher, A.; Fischer, M.; Diederich, F.; Schneider, G. Deorphaning pyrrolopyrazines as potent multi-target antimalarial agents Angew. Chem., Int. Ed. 2014, 53, 7079 - 7084
269. Krueger, A. C.; Madigan, D. L.; Beno, D. W.; Betebenner, D. A.; Carrick, R.; Green, B. E.; He, W.; Liu, D.; Maring, C. J.; McDaniel, K. F.; Mo, H.; Molla, A.; Motter, C. E.; Pilot-Matias, T. J.; Tufano, M. D.; Kempf, D. J. Novel hepatitis C virus replicon inhibitors: synthesis and structure-activity relationships of fused pyrimidine derivatives Bioorg. Med. Chem. Lett. 2012, 22, 2212 - 2215
270. DeGoey, D. A.; Betebenner, D. A.; Grampovnik, D. J.; Liu, D.; Pratt, J. K.; Tufano, M. D.; He, W.; Krishnan, P.; Pilot-Matias, T. J.; Marsh, K. C.; Molla, A.; Kempf, D. J.; Maring, C. J. Discovery of pyrido[2,3-d]pyrimidine-based inhibitors of HCV NS5A Bioorg. Med. Chem. Lett. 2013, 23, 3627 - 3630
271. Mugesh, G.; Singh, H. B.; Butcher, R. J. Non-bonded S···N interactions in organosulfur derivatives: crystal and molecular structures of [2-(4,4-dimethyl-2-oxazolinyl)phenyl] benzyl sulfide and bis[2-(4,4-dimethyl-2-oxazolinyl)phenyl] sulfide J. Chem. Res. 1999, 472 - 473
272. Morgan, R. S.; Tatsch, C. E.; Gushard, R. H.; McAdon, J. M.; Warme, P. K. Chains of alternating sulfur and π-bonded atoms in eight small proteins Int. J. Pept. Protein Res. 1978, 11, 209 - 217
273. Feldman, R. J. Atlas of Macromolecular Structure on Microfiche; Tracor-Jitco, Inc.: Rockville, MD, 1976.
274. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The Protein Data Bank Nucleic Acids Res. 2000, 28, 235 - 242
275. Bodner, B. L.; Jackman, L. M.; Morgan, R. S. Abstracts Annual Meeting Biophysical Society NMR evidence for a 1:1 complex between sulfur-containing and aromatic molecules Biophys. J. 1977, 17, 57a
276. Bodner, B. L.; Jackman, L. M.; Morgan, R. S. NMR study of 1:1 complexes between divalent sulfur and aromatic compounds: a model for interactions in globular proteins Biochem. Biophys. Res. Commun. 1980, 94, 807 - 813
277. Gibson, K. D.; Scheraga, H. A. Minimization of polypeptide energy. I. Preliminary structures of bovine pancreatic ribonuclease S-peptide Proc. Natl. Acad. Sci. U. S. A. 1967, 58, 420 - 427
278. Némethy, G.; Scheraga, H. A. Protein folding Q. Rev. Biophys. 1977, 10, 239 - 352
279. Morgan, R. S.; McAdon, J. M. Predictor for sulfur-aromatic interactions in globular proteins Int. J. Pept. Protein Res. 1980, 15, 177 - 180
280. Reid, K. S. C.; Lindley, P. F.; Thornton, J. M. Sulfur-aromatic interactions in proteins FEBS Lett. 1985, 190, 209 - 213
281. Pal, D.; Chakrabarti, P. Different types of interactions involving cysteine sulfhydryl group in proteins J. Biomol. Struct. Dynam. 1998, 15, 1059 - 1072
282. Zauhar, R. J.; Colbert, C. L.; Morgan, R. S.; Welsh, W. J. Evidence for a strong sulfur-aromatic interaction derived from crystallographic data Biopolymers 2000, 53, 233 - 248
283. Duan, G.; Smith, V. H., Jr.; Weaver, D. F. Characterization of aromatic-thiol π-type hydrogen bonding and phenylalanine-cysteine side chain interactions through ab initio calculations and protein database analyses Mol. Phys. 2001, 99, 1689 - 1699
284. Pal, D.; Chakrabarti, P. Non-hydrogen bond interactions involving the methionine sulfur atom J. Biomol. Struct. Dynam. 2001, 19, 115 - 128
285. Iwaoka, M.; Takemoto, S.; Okada, M.; Tomoda, S. Weak nonbonded S···X (X=O, N, S) interactions in proteins. Statistical and theoretical studies Bull. Chem. Soc. Jpn. 2002, 75, 1611 - 1625
286. Ringer, A. L.; Senenko, A.; Sherrill, C. D. Models of S/π interactions in protein structures: comparison of the H2S-benzene complex with PDB data Protein Sci. 2007, 16, 2216 - 2223
287. Valley, C. C.; Cembran, A.; Perlmutter, J. D.; Lewis, A. K.; Labello, N. P.; Gao, J.; Sachs, J. N. The methionine-aromatic motif plays a unique role in stabilizing protein structure J. Biol. Chem. 2012, 287, 34979 - 34991
288. Chakrabarti, P.; Bhattacharyya, R. Geometry of nonbonded interactions involving planar groups in proteins Prog. Biophys. Mol. Biol. 2007, 95, 83 - 137
289. Némethy, G.; Scheraga, H. A. Strong interaction between disulfide derivatives and aromatic groups in peptides and proteins Biochem. Biophys. Res. Commun. 1981, 98, 482 - 487
290. Cheney, B. V.; Schultz, M. W.; Cheney, J. Complexes of benzene with formamide and methanethiol as models for interactions of protein substructures Biochim. Biophys. Acta 1989, 996, 116 - 124
291. Pranata, J. Sulfur-aromatic interactions: a computational study of the DMS-benzene complex Bioorg. Chem. 1997, 25, 213 - 219
292. Tauer, T. P.; Derrick, M. E.; Sherrill, C. D. Estimates of the ab initio limit for sulfur-π interactions: the H2S-benzene dimer J. Phys. Chem. A 2005, 109, 191 - 196
293. Hermida-Ramón, J. M.; Cabaleiro-Lago; Rodriguez-Otero, J. Theoretical characterization of structures and energies of benzene-(H2S) n and (H2S) n (n = 1-4) clusters J. Chem. Phys. 2005, 122, 204315-1 - 204315-5
294. Morgado, C. A.; McNamara, J. P.; Hillier, I. A.; Burton, N. A.; Vincent, M. A. Density functional and semiempirical molecular orbital methods including dispersion corrections for the accurate description of noncovalent interactions involving sulfur-containing molecules J. Chem. Theory Comput. 2007, 3, 1656 - 1664
295. Lebl, M.; Sugg, E. E.; Hruby, V. J. Proton n.m.r. spectroscopic evidence for sulfur-aromatic interactions in peptides Int. J. Pept. Protein Res. 1987, 29, 40 - 45
296. Viguera, A. R.; Serrano, L. Side chain interactions between sulfur-containing amino acids and phenylalanine in α-helices Biochemistry 1995, 34, 8771 - 8779
297. Tatko, C. D.; Waters, M. L. Investigation of the nature of the methionine-π interaction in β-hairpin peptide model systems Protein Sci. 2004, 13, 2515 - 2522
298. Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with aromatic rings in chemical and biological recognition Angew. Chem., Int. Ed. 2003, 42, 1210 - 1250
299. Salonen, L. M.; Ellermann, M.; Diederich, F. Aromatic rings in chemical and biological recognition: energetics and structures Angew. Chem., Int. Ed. 2011, 50, 4804 - 4842
300. Brasch, J.; Harrison, O. J.; Ahlsen, G.; Liu, Q.; Shapiro, L. Crystal structure of domain VI and LE1 of human Netrin-G2 J. Mol. Biol. 2011, 414, 723 - 734
301. Harrop, S. J.; DeMaere, M. Z.; Fairlie, W. D.; Reztsova, T.; Valenzuela, S. M.; Mazzanti, M.; Tonini, R.; Qiu, M. R.; Jankova, L.; Warton, K.; Bauskin, A. R.; Wu, W. M.; Pankhurst, S.; Campbell, T. J.; Breit, S. N.; Curmi, P. M. Crystal structure of a soluble form of the intracellular chloride ion channel CLIC1 (NCC27) at 1.4 Å resolution J. Biol. Chem. 2001, 276, 44993 - 45000
302. Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising Acta Crystallogr., Sect. B: Struct. Sci. 2002, B58, 380 - 388
303. Karolak-Wojciechowska, J.; Kiec-Kononowicz, K. Structure of 6-(4-chlorobenzylidene)-2,3-dihydroimidazo[2,1- b ]thiazol-5(6 H)-one. Conformational analysis of Z isomers of 5-benzylidenethiohydantoin derivatives Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, C47, 2371 - 2374
304. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. New software for searching the Cambridge Structural Database and visualising crystal structures Acta Crystallogr., Sect. B: Struct. Sci. 2002, B58, 389 - 397
305. Gellman, S. H. On the role of methionine residues in the sequence-independent recognition of nonpolar protein surfaces Biochemistry 1991, 30, 6634 - 6636
306. Yoshida, T.; Mashima, A.; Sasahara, K.; Chuman, H. A simple and efficient dispersion correction to the Hartree-Fock theory Bioorg. Med. Chem. Lett. 2014, 24, 1037 - 1042.
307. Hymowitz, S. G.; Christinger, H. W.; Fuh, G.; Ultsch, M.; O'Connell, M.; Kelley, R. F.; Ashkenazi, A.; deVos, A. M. Triggering cell death: the crystal structure of Apo2L/TRAIL in a complex with death receptor 5 Mol. Cell 1999, 4, 563 - 571
308. Banner, D. W.; D'Arcy, A.; Janes, W.; Gentz, R.; Schoenfeld, H. J.; Broger, C.; Loetscher, H.; Lesslauer, W. Crystal structure of the soluble human 55 kD TNF receptor-human TNF beta complex: implications for TNF receptor activation Cell 1993, 73, 431 - 445
309. Williamson, M. P. Applications of the NOE in molecular biology Annu. Rep. NMR Spectrosc. 2009, 65, 77 - 109
310. Muñoz, V.; Serrano, L. Elucidating the folding problem of helical peptides using empirical parameters Nature Struct. Biol. 1994, 1, 399 - 409
311. Stapley, B. J.; Rohl, C. A.; Doig, A. J. Addition of side chain interactions to modified Lifson-Roig helix-coil theory: application to energetic of phenylalanine-methionine interactions Protein Sci. 1995, 4, 2383 - 2391
312. Cockroft, S. L.; Hunter, C. A. Chemical double-mutant cycles: dissecting non-covalent interactions Chem. Soc. Rev. 2007, 36, 172 - 188
313. Kawai, S. H.; Bailey, M. D.; Halmos, T.; Forgione, P.; LaPlante, S. R.; Llinas-Brunet, M.; Naud, J.; Goudreau, N. The use of chemical double-mutant cycles in biomolecular recognition studies: application to HCV NS3 protease inhibitors ChemMedChem 2008, 3, 1654 - 1657
314. Motherwell, W. B.; Joëlle, M.; Aliev, A. E.; Nič, M.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Chessari, G.; Hunter, C. A.; Vinter, J. G. Noncovalent functional-group-arene interactions Angew. Chem., Int. Ed. 2007, 46, 7823 - 7826
315. Druhan, L. J.; Swenson, R. P. Role of methionine 56 in the control of the oxidation-reduction potentials of the Clostridium beijerinckii flavodoxin; effects of substitutions by aliphatic amino acids and evidence for a role of sulfur-flavin interactions Biochemistry 1998, 37, 9668 - 9678
316. Ludwig, M. L.; Pattridge, K. A.; Metzger, A. L.; Dixon, M. M.; Eren, M.; Feng, Y.; Swenson, R. P. Control of oxidation-reduction potentials in flavodoxin from Clostridium beijerinckii: the role of conformation changes Biochemistry 1997, 36, 1259 - 1280
317. Traxler, P.; Gren, J.; Mett, H.; Séquin, U.; Furet, P. Use of a pharmacophore model for the design of EGFR tyrosine kinase inhibitors: isoflavones and 3-phenyl-4(1 H)-quinolones J. Med. Chem. 1999, 42, 1018 - 1026
318. Peng, T.; Pei, J.; Zhou, J. 3D-QSAR and receptor modeling of tyrosine kinase inhibitors with flexible atom receptor model (FLARM) J. Chem. Inf. Comput. Sci. 2003, 43, 298 - 303
319. Visser, F.; Vickers, M. F.; Ng, A. M.; Baldwin, S. A.; Young, J. D.; Cass, C. E. Mutation of residue 33 of human equilibrative nucleoside transporters 1 and 2 alters sensitivity to inhibition of transport by dilazep and dipyridamole J. Biol. Chem. 2002, 277, 395 - 401
320. Visser, F.; Zhang, J.; Raborn, R. T.; Baldwin, S. A.; Young, J. D.; Cass, C. E. Residue 33 of human equilibrative nucleoside transporter 2 is a functionally important component of both the dipyridamole and nucleoside binding sites Mol. Pharmacol. 2005, 67, 1291 - 1298
321. Wogulis, M.; Wheelock, C. E.; Kamita, S. G.; Hinton, A. C.; Whetstone, P. A.; Hammock, B. D.; Wilson, D. K. Structural studies of a potent insect maturation inhibitor bound to the juvenile hormone esterase of Manduca sexta Biochemistry 2006, 45, 4045 - 4057
322. Heelock, C. E.; Colvin, M. E.; Uemura, I.; Olmstead, M. M.; Sanborn, J. R.; Nakagawa, Y.; Jones, A. D.; Hammock, B. D. Use of ab initio calculations to predict the biological activity of carboxylesterase inhibitors J. Med. Chem. 2002, 45, 5576 - 5593
323. Probst, G. D.; Bowers, S.; Sealy, J. M.; Truong, A. P.; Horn, R. K.; Galemmo, R. A., Jr.; Konradi, A. W.; Sham, H. L.; Quincy, D. A.; Pan, H.; Yao, N.; Lin, M.; Tóth, G.; Artis, D. R.; Zmolek, W.; Wong, K.; Qin, A.; Lorentzen, C.; Nakamura, D. F.; Quinn, K. P.; Sauer, J.-M.; Powell, K.; Ruslim, L.; Wright, S.; Chereau, D.; Ren, Z.; Anderson, J. P.; Bard, F.; Yednock, T. A.; Griswold-Prenner, I. Highly selective c-Jun N-terminal kinase (JNK) 2 and 3 inhibitors with in vitro CNS-like pharmacokinetic properties prevent neurodegradation Bioorg. Med. Chem. Lett. 2011, 21, 315 - 319
324. Daeffler, K. N.-M.; Lester, H. A.; Dougherty, D. A. Functionally important aromatic-aromatic and sulfur-π interactions in the D2 dopamine receptor J. Am. Chem. Soc. 2012, 134, 14890 - 14896
325. Chien, E. Y. T.; Liu, W.; Zhao, Q.; Katritch, V.; Won Han, G.; Hanson, M. A.; Shi, L.; Newman, A. H.; Javitch, J. A.; Cherezov, V.; Stevens, R. C. Structure of the human dopamine D3 receptor in complex with a D2/D3 selective antagonist Science 2010, 330, 1091 - 1095
326. LaPlante, S. R.; Nar, H.; Lemke, C. T.; Jakalian, A.; Aubry, N.; Kawai, S. H. Ligand bioactive conformation plays a critical role in the design of drugs that target the hepatitis C virus NS3 protease J. Med. Chem. 2014, 57, 1777 - 1789
327. Llinàs-Brunet, M.; Bailey, M.; Fazal, G.; Goulet, S.; Halmos, T.; LaPlante, S.; Maurice, R.; Poirier, M.; Poupart, M.-A.; Thibeault, D.; Wernic, D.; Lamarre, D. Peptide-based inhibitors of the hepatitis C virus serine protease Bioorg. Med. Chem. Lett. 1998, 8, 1713 - 1718
328. Llinàs-Brunet, M.; Bailey, M.; Déziel, R.; Fazal, G.; Gorys, V.; Goulet, S.; Halmos, T.; Maurice, R.; Poirier, M.; Poupart, M.-A.; Rancourt, J.; Thibeault, D.; Wernic, D.; Lamarre, D. Studies on the C-terminal of hexapeptide inhibitors of the hepatitis C virus serine protease Bioorg. Med. Chem. Lett. 1998, 8, 2719 - 2724
329. Kakiuchi, N.; Hijikata, M.; Komoda, Y.; Tanji, Y.; Hirowatori, Y.; Shimotohno, K. Bacterial expression and analysis of cleavage activity of HCV serine proteinase using recombinant and synthetic substrate Biochem. Biophys. Res. Commun. 1995, 210, 1059 - 1065
330. Politzer, P.; Murray, J. M.; Clark, T. Halogen bonding: an electrostatically-driven highly directional noncovalent interaction Phys. Chem. Chem. Phys. 2010, 12, 7748 - 7757
331. Aufinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Halogen bonds in biological macromolecules Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 16789 - 16794
332. Wilcken, R.; Zimmermann, M. O.; Lange, A.; Zahn, S.; Kirchner, B.; Boeckler, F. M. Addressing methionine in molecular design through directed sulfur-halogen bonds J. Chem. Theory Comput. 2011, 7, 2307 - 2315
333. Hauchecorne, D.; Moiana, A.; van der Veken, B.; Herrebout, W. A. Halogen bonding to a divalent sulfur atom: an experimental study of the interactions of CF3X (X = Cl, Br, I) with dimethyl sulfide Phys. Chem. Chem. Phys. 2011, 13, 10204 - 10213
334. Liu, l.; Baase, W. A.; Matthews, B. W. Halogenated benzenes bound within a non-polar cavity in T4 lysozyme provide examples of I···S and I···Se halogen-bonding J. Mol. Biol. 2009, 385, 595 - 605
335. Rush, T. S., III; Grant, A.; Mosyak, L.; Nicholls, A. A shape-based 3-D scaffold hopping method and its application to a bacterial protein-protein interaction J. Med. Chem. 2005, 48, 1489 - 1495
336. Ferreira, R. S.; Simeonov, A.; Jadhav, A.; Eidam, O.; Mott, B. T.; Keiser, M. J.; McKerrow, J. H.; Maloney, D. J.; Irwin, J. J.; Shoichet, B. K. Complementarity between a docking and a high-throughput screen in discovering new cruzain inhibitors J. Med. Chem. 2010, 53, 4891 - 4905
337. Katz, B. A.; Sprengeler, P. A.; Luong, C.; Verner, E.; Elrod, K.; Kirtley, M.; Janc, J.; Spencer, J. R.; Breitenbucher, J. G.; Hui, H.; McGee, D.; Allen, D.; Martelli, A.; Mackman, R. L. Engineering inhibitors highly selective for the S1 sites of Ser190 trypsin-like serine protease targets Chem. Biol. 2001, 8, 1107 - 1121
338. Alam, M.; Beevers, R. E.; Ceska, T.; Davenport, R. J.; Dickson, K. M.; Fortunato, M.; Gowers, L.; Haughan, A. F.; James, L. A.; Jones, M. W.; Kinsella, N.; Lowe, C.; Meissner, J. W. G.; Nicolas, A.-L.; Perry, B. G.; Philips, D. J.; Pitt, W. R.; Platt, A.; Ratcliffe, A. J.; Sharpe, A.; Tait, L. J. Synthesis and SAR of aminopyrimidines as novel c-Jun N-terminal kinase (JNK) inhibitors Bioorg. Med. Chem. Lett. 2007, 17, 3463 - 3467
339. Huang, X.; Cheng, C. C.; Fischmann, T. O.; Duca, J. S.; Yang, X.; Richards, M.; Shipps, G. W., Jr. Discovery of a novel series of CHK1 kinase inhibitors with a distinctive hinge binding mode ACS Med. Chem. Lett. 2012, 3, 123 - 128
340. Huang, X.; Cheng, C. C.; Fischmann, T. O.; Duca, J. S.; Richards, M.; Tadikonda, P. K.; Adulla Reddy, P.; Zhao, L.; Siddiqui, M. A.; Parry, D.; Davis, N.; Seghezzi, W.; Wiswell, D.; Shipps, G. W., Jr. Structure-based design and optimization of 2-aminothiazole-4-carboxamide as a new class of CHK1 inhibitors Bioorg. Med. Chem. Lett. 2013, 23, 2590 - 2594
341. Hua, Z.; Bregman, H.; Buchanan, J. L.; Chakka, N.; Guzman-Perez, A.; Gunaydin, H.; Huang, X.; Gu, Y.; Berry, V.; Liu, J.; Teffera, Y.; Huang, L.; Egge, B.; Emkey, R.; Mullady, E. L.; Schneider, S.; Andrews, P. S.; Acquaviva, L.; Dovey, J.; Mishra, A.; Newcomb, J.; Saffran, D.; Serafino, R.; Strathdee, C. A.; Turci, S. M.; Stanton, M.; Wilson, C.; DiMauro, E. F. Development of novel dual binders as potent, selective, and orally bioavailable tankyrase inhibitors J. Med. Chem. 2013, 56, 10003 - 10015
342. Pierce, A. C.; Sandretto, K. L.; Bemis, G. W. Kinase inhibitors and the case for CH···O hydrogen bonds in protein-ligand binding Proteins: Struct. Funct. Genet. 2002, 49, 567 - 576