Correction to: Atropisomer Control in Macrocyclic Factor VIIa Inhibitors (Journal of Medicinal Chemistry (2016) 59:8 (4007-4018) DOI: 10.1021/acs.jmedchem.6b00244);Atropisomer Control in Macrocyclic Factor VIIa Inhibitors

Journal of Medicinal Chemistry

Volumn 59, Issue 8, 2016, Pages 4007-4018

  Glunz, Peter W ^a   Mueller, Luciano ^a   Cheney, Daniel L ^a   Ladziata, Vladimir ^a   Zou, Yan ^a   Wurtz, Nicholas R ^a   Wei, Anzhi ^a   Wong, Pancras C ^a   Wexler, Ruth R ^a   Priestley, E Scott ^a  

^a BRISTOL MYERS SQUIBB RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ALLYL 4 BROMO 2 METHYLBENZENE; 2 (1 AMINOISOQUINOLIN 6 YLAMINO) 20 METHYL 13 OXA 4,11 DIAZATRICYCLO[14.2.2.16,10]HENICOSA 1(19),6,8,10(21),16(20),17 HEXAENE 3,12 DIONE TRIFLUOROACETIC ACID SALT; 2 (4 BROMO 2 METHYLPHENYL)ACETIC ACID; 2 (4 BROMO 2 METHYLPHENYL)PROPAN 1 OL; 2 [(1 AMINOISOQUINOLIN 6 YL)AMINO] 15,17 DIMETHYL 13 OXA 4,11 DIAZATRICYCLO[14.2.2.16,10]HENICOSA 1(18),6,8,10(21),16,19 HEXAENE 3,12 DIONE TRIFLUOROACETIC ACID; 2 [(1 AMINOISOQUINOLIN 6 YL)AMINO] 15,17 DIMETHYL 13 OXA 4,11 DIAZATRICYCLO[14.2.2.16,10]HENICOSA 1(18),6,8,10(21),16,19 HEXAENE 3,12 DIONE, TRIFLUOROACETIC ACID SALT; 2 [4 [2 [3 (AMINOMETHYL)PHENYLCARBAMOYLOXY]ETHYL] 3 METHYLPHENYL] 2 [5 [BIS(TERT BUTOXYCARBONYL)AMINO]NAPHTHALEN 2 YLAMINO]ACETIC ACID; 2 [5 [BIS(TERT BUTOXYCARBONYL)AMINO]NAPHTHALEN 2 YLAMINO] 2 [4 [2 (3 CYANOPHENYLCARBAMOYLOXY)ETHYL] 3 METHYLPHENYL]ACETIC ACID; 4 BENZYL 3 [2 (4 BROMO 2 METHYLPHENYL)ACETYL]OXAZOLIDIN 2 ONE; 4 BROMO 2 METHYLPHENETHYL 3 CYANOPHENYLCARBAMATE; 4 [2 (3 CYANOPHENYLCARBAMOYLOXY)ETHYL] 3 METHYLPHENYLBORONIC ACID; BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 11A; BLOOD CLOTTING FACTOR 7A; BLOOD CLOTTING FACTOR 7A INHIBITOR; MACROCYCLIC COMPOUND; METHYL GROUP; TERT BUTYL N [6 [[[[(3 AMINOPHENYL)METHYL](METHYL)CARBAMOYL][[4 (1 HYDROXYPROPAN 2 YL) 3 METHYLPHENYL]]METHYL]AMINO]ISOQUINOLIN 1 YL] N [(TERT BUTOXY)CARBONYL]CARBAMATE; TERT BUTYL N [6 [[[[(3 AMINOPHENYL)METHYL]CARBAMOYL][[4 (1 HYDROXYPROPAN 2 YL) 3 METHYLPHENYL]]METHYL]AMINO]ISOQUINOLIN 1 YL] N [(TERT BUTOXY)CARBONYL]CARBAMATE; THROMBIN; TISSUE KALLIKREIN; TRYPSIN; UNCLASSIFIED DRUG; [4 (1 HYDROXYPROPAN 2 YL) 3-METHYLPHENYL]BORONIC ACID; SERINE PROTEINASE INHIBITOR;

ALKYLATION; ALLYLATION; ARTICLE; ATROPISOMER; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIASTEREOISOMER; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HETERONUCLEAR SINGLE QUANTUM COHERENCE; ISOMER; NUCLEAR OVERHAUSER EFFECT; PROCESS OPTIMIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CRYSTALLOGRAPHY, X-RAY; FACTOR VIIA; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SERINE PROTEINASE INHIBITORS;

EID: 84966393530     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.8b00465     Document Type: Erratum

References (42)

1. Oki, M. Recent advances in atropisomerism. In Topics in Stereochemistry; John Wiley & Sons, Inc.: Hoboken, NJ, 2007; pp 1-81.
2. Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Atroposelective synthesis of axially chiral biaryl compounds Angew. Chem., Int. Ed. 2005, 44, 5384-5427 10.1002/anie.200462661
3. Singh, S. B.; Jayasuriya, H.; Salituro, G. M.; Zink, D. L.; Shafiee, A.; Heimbuch, B.; Silverman, K. C.; Lingham, R. B.; Genilloud, O.; Teran, A.; Vilella, D.; Felock, P.; Hazuda, D. The Complestatins as HIV-1 integrase inhibitors. Efficient isolation, structure elucidation, and inhibitory activities of isocomplestatin, chloropeptin I, new complestatins, A and B, and acid-hydrolysis products of chloropeptin I J. Nat. Prod. 2001, 64, 874-882 10.1021/np000632z
4. Shimamura, H.; Breazzano, S. P.; Garfunkle, J.; Kimball, F. S.; Trzupek, J. D.; Boger, D. L. Total synthesis of complestatin: Development of a Pd(0)-mediated indole annulation for macrocyclization J. Am. Chem. Soc. 2010, 132, 7776-7783 10.1021/ja102304p
5. Schäfer, M.; Schneider, T. R.; Sheldrick, G. M. Crystal structure of vancomycin Structure 1996, 4, 1509-1515 10.1016/S0969-2126(96)00156-6
6. Boger, D. L.; Loiseleur, O.; Castle, S. L.; Beresis, R. T.; Wu, J. H. Thermal atropisomerism of fully functionalized vancomycin CD, DE, and CDE ring systems Bioorg. Med. Chem. Lett. 1997, 7, 3199-3202 10.1016/S0960-894X(97)10182-2
7. LaPlante, S. R.; Edwards, P. J.; Fader, L. D.; Jakalian, A.; Hucke, O. Revealing atropisomer axial chirality in drug discovery ChemMedChem 2011, 6, 505-513 10.1002/cmdc.201000485
8. Clayden, J.; Moran, W. J.; Edwards, P. J.; LaPlante, S. R. The challenge of atropisomerism in drug discovery Angew. Chem., Int. Ed. 2009, 48, 6398-6401 10.1002/anie.200901719
9. Driggers, E. M.; Hale, S. P.; Lee, J.; Terrett, N. K. The exploration of macrocycles for drug discovery-an underexploited structural class Nat. Rev. Drug Discovery 2008, 7, 608-624 10.1038/nrd2590
10. Mallinson, J.; Collins, I. Macrocycles in new drug discovery Future Med. Chem. 2012, 4, 1409-1438 10.4155/fmc.12.93
11. Priestley, E. S.; Cheney, D. L.; DeLucca, I.; Wei, A.; Luettgen, J. M.; Rendina, A. R.; Wong, P. C.; Wexler, R. R. Structure-based design of macrocyclic coagulation Factor VIIa inhibitors J. Med. Chem. 2015, 58, 6225-6236 10.1021/acs.jmedchem.5b00788
12. Kadono, S.; Sakamoto, A.; Kikuchi, Y.; Oh-eda, M.; Yabuta, N.; Koga, T.; Hattori, K.; Shiraishi, T.; Haramura, M.; Kodama, H.; Esaki, T.; Sato, H.; Watanabe, Y.; Itoh, S.; Ohta, M.; Kozono, T. Peptide mimetic factor VIIa inhibitor: Importance of hydrophilic pocket in S2 site to improve selectivity against thrombin Lett. Drug Des. Discovery 2005, 2, 177-181 10.2174/1570180053765200
13. Krishnan, R.; Kotian, P. L.; Chand, P.; Bantia, S.; Rowland, S.; Babu, Y. S. Probing the S2 site of factor VIIa to generate potent and selective inhibitors: the structure of BCX-3607 in complex with tissue factor-factor VIIa Acta Crystallogr., Sect. D: Biol. Crystallogr. 2007, 63, 689-697 10.1107/S0907444907014187
14. The PyMOL Molecular Graphics System, Version 1.7; Schrödinger, LLC.
15. Petasis, N. A.; Zavialov, I. A. A new and practical synthesis of α-amino acids from alkenyl boronic acids J. Am. Chem. Soc. 1997, 119, 445-446 10.1021/ja963178n
16. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Boronic acids and esters in the Petasis-borono Mannich multicomponent reaction Chem. Rev. 2010, 110, 6169-6193 10.1021/cr100108k
17. Glunz, P. W.; Bisacchi, G. S.; Morton, G. C.; Holubec, A. A.; Priestley, E. S.; Zhang, X.; Treuner, U. D. Preparation of phenylglycine sulfonamide derivatives useful as serine protease inhibitors. WO2004072101A2, 2004.
18. Borgono, C. A.; Diamandis, E. P. The emerging roles of human tissue kallikreins in cancer Nat. Rev. Cancer 2004, 4, 876-890 10.1038/nrc1474
19. Prassas, I.; Eissa, A.; Poda, G.; Diamandis, E. P. Unleashing the therapeutic potential of human kallikrein-related serine proteases Nat. Rev. Drug Discovery 2015, 14, 183-202 10.1038/nrd4534
20. Zhang, X.; Glunz, P. W.; Johnson, J. A.; Jiang, W.; Jacutin-Porte, S.; Ladziata, V.; Phillips, M. S.; Wurtz, N. R.; Parkhurst, B.; Rendina, A. R.; Harper, T. M.; Cheney, D. L.; Luettgen, J. M.; Wong, P. C.; Seiffert, D.; Wexler, R. R.; Priestley, E. S. Discovery of a highly potent, selective, and orally bioavailable macrocyclic inhibitor of blood coagulation factor VIIa-tissue factor complex. In preparation.
21. Wong, P. C.; Luettgen, J. M.; Rendina, A. R.; Kettner, C. A.; Xin, B.; Knabb, R. M.; Wexler, R.; Priestley, E. S. BMS-593214, an active site-directed factor VIIa inhibitor: Enzyme kinetics, antithrombotic and antihaemostatic studies Thromb. Haemostasis 2010, 104, 261-269 10.1160/TH10-01-0025
22. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode Methods Enzymol. 1997, 276, 307-326 10.1016/S0076-6879(97)76066-X
23. Brünger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J.-S.; Kuszewski, J.; Nilges, M.; Pannu, N. S. Crystallography & NMR system: A new software suite for macromolecular structure determination Acta Crystallogr., Sect. D: Biol. Crystallogr. 1998, 54, 905-921 10.1107/S0907444998003254
24. Emsley, P.; Lohkamp, B.; Scott, W. G.; Cowtan, K. Features and development of Coot Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 486-501 10.1107/S0907444910007493
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
26. Shao, Y.; Gan, Z.; Epifanovsky, E.; Gilbert, A. T. B.; Wormit, M.; Kussmann, J.; Lange, A. W.; Behn, A.; Deng, J.; Feng, X.; Ghosh, D.; Goldey, M.; Horn, P. R.; Jacobson, L. D.; Kaliman, I.; Khaliullin, R. Z.; Kuś, T.; Landau, A.; Liu, J.; Proynov, E. I.; Rhee, Y. M.; Richard, R. M.; Rohrdanz, M. A.; Steele, R. P.; Sundstrom, E. J.; Woodcock, H. L.; Zimmerman, P. M.; Zuev, D.; Albrecht, B.; Alguire, E.; Austin, B.; Beran, G. J. O.; Bernard, Y. A.; Berquist, E.; Brandhorst, K.; Bravaya, K. B.; Brown, S. T.; Casanova, D.; Chang, C.-M.; Chen, Y.; Chien, S. H.; Closser, K. D.; Crittenden, D. L.; Diedenhofen, M.; DiStasio, R. A.; Do, H.; Dutoi, A. D.; Edgar, R. G.; Fatehi, S.; Fusti-Molnar, L.; Ghysels, A.; Golubeva-Zadorozhnaya, A.; Gomes, J.; Hanson-Heine, M. W. D.; Harbach, P. H. P.; Hauser, A. W.; Hohenstein, E. G.; Holden, Z. C.; Jagau, T.-C.; Ji, H.; Kaduk, B.; Khistyaev, K.; Kim, J.; Kim, J.; King, R. A.; Klunzinger, P.; Kosenkov, D.; Kowalczyk, T.; Krauter, C. M.; Lao, K. U.; Laurent, A. D.; Lawler, K. V.; Levchenko, S. V.; Lin, C. Y.; Liu, F.; Livshits, E.; Lochan, R. C.; Luenser, A.; Manohar, P.; Manzer, S. F.; Mao, S.-P.; Mardirossian, N.; Marenich, A. V.; Maurer, S. A.; Mayhall, N. J.; Neuscamman, E.; Oana, C. M.; Olivares-Amaya, R.; O'Neill, D. P.; Parkhill, J. A.; Perrine, T. M.; Peverati, R.; Prociuk, A.; Rehn, D. R.; Rosta, E.; Russ, N. J.; Sharada, S. M.; Sharma, S.; Small, D. W.; Sodt, A.; Stein, T.; Stück, D.; Su, Y.-C.; Thom, A. J. W.; Tsuchimochi, T.; Vanovschi, V.; Vogt, L.; Vydrov, O.; Wang, T.; Watson, M. A.; Wenzel, J.; White, A.; Williams, C. F.; Yang, J.; Yeganeh, S.; Yost, S. R.; You, Z.-Q.; Zhang, I. Y.; Zhang, X.; Zhao, Y.; Brooks, B. R.; Chan, G. K. L.; Chipman, D. M.; Cramer, C. J.; Goddard, W. A.; Gordon, M. S.; Hehre, W. J.; Klamt, A.; Schaefer, H. F.; Schmidt, M. W.; Sherrill, C. D.; Truhlar, D. G.; Warshel, A.; Xu, X.; Aspuru-Guzik, A.; Baer, R.; Bell, A. T.; Besley, N. A.; Chai, J.-D.; Dreuw, A.; Dunietz, B. D.; Furlani, T. R.; Gwaltney, S. R.; Hsu, C.-P.; Jung, Y.; Kong, J.; Lambrecht, D. S.; Liang, W.; Ochsenfeld, C.; Rassolov, V. A.; Slipchenko, L. V.; Subotnik, J. E.; Van Voorhis, T.; Herbert, J. M.; Krylov, A. I.; Gill, P. M. W.; Head-Gordon, M. Advances in molecular quantum chemistry contained in the Q-Chem 4 program package Mol. Phys. 2015, 113, 184-215 10.1080/00268976.2014.952696
27. MacroModel, Version 10.5; Schrödinger, LLC: New York, NY, 2014
28. Watts, K. S.; Dalal, P.; Tebben, A. J.; Cheney, D. L.; Shelley, J. C. Macrocycle conformational sampling with MacroModel J. Chem. Inf. Model. 2014, 54, 2680-2696 10.1021/ci5001696
29. Maestro, Version 9.9; Schrödinger, LLC: New York, NY, 2014.
30. ACD/NMR, v. 10; Advanced Chemistry Development, Inc.: Toronto, ON, Canada, 2006; www.acdlabs.com.
31. States, D. J.; Haberkorn, R. A.; Ruben, D. J. A two-dimensional nuclear Overhauser experiment with pure absorption phase in four quadrants J. Magn. Reson. 1982, 48, 286-292 10.1016/0022-2364(82)90279-7
32. Ernst, R. R.; Bodenhausen, G.; Wokaun, A. Principles of Nuclear Magnetic Resonance in One and Two Dimensions; Clarendon Press: Oxford, 1987; Vol. 14.
33. Neuhaus, D.; Sheppard, R. N.; Bick, I. R. C. Structural and conformational study of repanduline using long-range nuclear Overhauser effect difference spectroscopy J. Am. Chem. Soc. 1983, 105, 5996-6002 10.1021/ja00357a006
34. Aue, W. P.; Bartholdi, E.; Ernst, R. R. Two-dimensional spectroscopy. Application to nuclear magnetic resonance J. Chem. Phys. 1976, 64, 2229-2246 10.1063/1.432450
35. Mueller, L. P. E.COSY, a simple alternative to E.COSY J. Magn. Reson. 1987, 72, 191-6 10.1016/0022-2364(87)90188-0
36. Bax, A.; Davis, D. G. MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy J. Magn. Reson. 1985, 65, 355-360 10.1016/0022-2364(85)90018-6
37. Braunschweiler, L.; Ernst, R. R. Coherence transfer by isotropic mixing: application to proton correlation spectroscopy J. Magn. Reson. 1983, 53, 521-528 10.1016/0022-2364(83)90226-3
38. Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. Investigation of exchange processes by two-dimensional NMR spectroscopy J. Chem. Phys. 1979, 71, 4546-4553 10.1063/1.438208
39. Kumar, A.; Ernst, R. R.; Wuthrich, K. A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules Biochem. Biophys. Res. Commun. 1980, 95, 1-6 10.1016/0006-291X(80)90695-6
40. Schmieder, P.; Domket, T.; Norris, D. G.; Kurz, M.; Kessler, H.; Leibfritz, D. Editing of multiplicity in two- and three-dimensional heteronuclear NMR spectroscopy by Fourier transformation of the pulse-angle dependency J. Magn. Reson. 1991, 93, 430-435 10.1016/0022-2364(91)90021-K
41. Cicero, D. O.; Barbato, G.; Bazzo, R. Sensitivity enhancement of a two-dimensional experiment for the measurement of heteronuclear long-range coupling constants, by a new scheme of coherence selection by gradients J. Magn. Reson. 2001, 148, 209-213 10.1006/jmre.2000.2234
42. Sousa da Silva, A. W.; Vranken, W. F. ACPYPE-AnteChamber PYthon Parser interfacE BMC Res. Notes 2012, 5, 367-367 10.1186/1756-0500-5-367