Erratum to: Improving Solubility via Structural Modification (Topics in Medicinal Chemistry, (69), 10.1007/7355_2013_32);Improving solubility via structural modification

Topics in Medicinal Chemistry

Volumn 9, Issue , 2014, Pages 69-106

  Walker, Michael A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Crystal lattice stability; Enthalpy of solvation; Entropy of solvation; Fluorine; General solubility equation; Hydrogen bonding; Hydrophobicity; Matched molecular pairs; Melting point; Molecular planarity; Molecular symmetry; Packing efficiency; Solubilizing appendage; Solvation; X Ray crystallography

Indexed keywords

ANTIBIOTIC AGENT; FLUORINE; LEFLUNOMIDE; ORGANIC COMPOUND; PHOSPHODIESTERASE IV INHIBITOR; PROTEIN KINASE B INHIBITOR; THALIDOMIDE; TUBERCULOSTATIC AGENT; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DRUG SOLUBILITY; DRUG STRUCTURE; GENERAL SOLUBILITY EQUATION; HYDROGEN BOND; HYDROPHOBICITY; MATHEMATICAL PARAMETERS; MELTING POINT; MOLECULAR INTERACTION; MOLECULAR SIZE; SOLID STATE; SOLUTE; SOLVATION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 84916212125     PISSN: 18622461     EISSN: 1862247X     Source Type: Book Series    
DOI: 10.1007/7355_2014_71     Document Type: Erratum

References (96)

1. Amidon GL, Lennernäs HL, Shah VP, Crison JR (1995) A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 12:413–420
2. Lipinski CA (2000) Drug-like properties and the causes of poor solubility and poor permeability. J Pharm Tox Meth 44:235–249
3. Lovering F, Bikker J, Humblet C (2009) Escape from flatland: increasing saturation as an approach to improving clinical success. J Med Chem 52:6752–6756
4. Ritchie TJ, Macdonald SJF (2009) The impact of aromatic ring count on compound developability – are too many aromatic rings a liability in drug design? Drug Disc Today 14:1011–1020
5. Hill AP, Young RJ (2010) Getting physical in drug discovery: a contemporary perspective on solubility and hydrophobicity. Drug Disc Today 15:649–655
6. Yang Y, Engkvist O, Llinàs A, Chen H (2012) Beyond size, ionization state, and lipophilicity: influence of molecular topology on absorption, distribution, metabolism, excretion, and toxicity for drug like compounds. J Med Chem 55:3667–3677
7. Hann MM (2011) Molecular obesity, potency and other addictions in drug discovery. Med Chem Comm 2:349–355
8. Faller B, Ottaviani G, Ertl P et al (2011) Evolution of the physicochemical properties of marketed drugs: can history foretell the future? Drug Discov Today 16:976–984
9. Di L, Fish PV, Mano T (2012) Bridging solubility between drug discovery and development. Drug Discov Today 17:486–495
10. Meanwell NA (2011) Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem Res Toxicol 24: 1420–1456
11. Ran Y, Yalkowsky SH (2001) Prediction of drug solubility by the general solubility equation (GSE). J Chem Inf Comput Sci 41:354–357
12. Ran Y, Jain N, Yalkowsky SH (2001) Prediction of aqueous solubility of organic compounds by the general solubility equation (GSE). J Chem Inf Comput Sci 41:1208–1217
13. Ben-Naim A (2001) On the evolution of the concept of solvation thermodynamics. J Sol Chem 30:475–487
14. Frank HS, Evans MW (1945) Free volume and entropy in condensed systems. III. Entropy in binary liquid mixtures; partial molal entropy in dilute solutions; structure and thermodynamics in aqueous electrolytes. J Chem Phys 13:507–532
15. Ben-Naim A, Tenne R (1977) Application of the scaled particle theory to the problem of hydrophobic interaction. J Chem Phys 67:627–635
16. Lee B, Graziano G (1996) A two-state model of hydrophobic hydration that produces compensating enthalpy and entropy changes. J Am Chem Soc 118:5163–5168
17. Reiss H, Frisch HL, Lebowitz JL (1959) Statistical mechanics of rigid spheres. J Chem Phys 31:369–380
18. Tolls J, van Dijk J, Verbruggen EJM et al (2002) Aqueous solubility-molecular size relationships: a mechanistic case study using C10- to C19-alkanes. J Phys Chem A 106:2760–2765
19. Khadikar RV, Mandloi D, Bajaj AV, Joshi S (2003) QSAR Study on solubility of alkanes in water and their partition coefficients in different solvent systems using PI index. Bioorg Med Chem Lett 13:419–422
20. Ferguson AL, Debenedetti PG, Panagiotopoulos AZ (2009) Solubility and molecular conformations of n-alkane chains in water. J Phys Chem B 113:6405–6414
21. Abraham MH, Ibrahim A, Zissimos AM et al (2002) Application of hydrogen bonding calculations in property based drug design. Drug Discov Today 7:1056–1063
22. Raevsky O (2008) H-Bonding parameterization in quantitative structure–activity relationships and drug design. In: Mannhold R (ed) Molecular drug properties. Wiley-VCH, Weinheim
23. Gurka D, Taft RW (1969) Studies of hydrogen-bonded complex formation with p-fluorophenol. IV. Fluorine nuclear magnetic resonance method. J Am Chem Soc 91:4794–4801
24. Arnett EM, Joris L, Mitchell E et al (1970) Hydrogen-bonded complex formation. III. Thermodynamics of complexing by infrared spectroscopy and calorimetry. J Am Chem Soc 92:2365–2377
25. Berthelot M, Laurence C, Safar M, Besseau F (1998) Hydrogen-bond basicity pKHB scale of six-membered aromatic N-heterocycles. J Chem Soc Perkin Trans 2:283–290
26. Laurence C, Brameld KA, Graton J et al (2009) The pK(BHX) database: toward a better understanding of hydrogen-bond basicity for medicinal chemists. J Med Chem 52:4073–4086
27. Yalkowsky SH, Valvani SC (1980) Solubility and partitioning I: solubility of nonelectrolytes in water. J Pharm Sci 69:912–922
28. Dannenfelser RM, Yalkowsky SH (1996) Estimation of entropy of melting from molecular structure: a non-group contribution method. Ind Eng Chem Res 35:1483–1486
29. Chickos JS, Braton CM, Hesse DG, Liebman JF (1991) Estimating entropies and enthalpies of fusion of organic compounds. J Org Chem 56:927–938
30. Dunitz JD, Filippini G, Gavezzotti A (2000) Molecular shape and crystal packing: a study of C12H12 isomers, real and imaginary. Helv Chim Acta 83:2317–2335
31. Du Y, Creighton CJ, Tounge BA, Reitz AP (2004) Noncovalent self-assembly of bicyclo [4.2.2]diketopiperazines: influence of saturation in the bridging carbacyclic ring. Org Lett 6: 306–312
32. Dunitz JD, Gavezzotti A (2009) How molecules stick together in organic crystals: weak intermolecular interactions. Chem Soc Rev 38:2622–2633
33. Zhang J, Wang Y, Wang Q, Xu L (2012) 6,7-Dichloro-3-(2,4-dichlorobenzyl)- quinoxalin-2 (1H)-one. Acta Crystallogr Sect E 68:2481
34. Zhou Y, Ren L, Lu Y, Zhang F, Chen G (2012) N-[4-Chloro-3-(trifluoromethyl)phenyl]- 2,2-dimethylpropanamide. Acta Cryst Sect E 68:2534
35. Gavezzotti A, Filippini G (1994) Geometry of the intermolecular X-H-Y (X, Y = N, O) hydrogen-bond and the calibration of empirical hydrogen-bond potentials. J Phys Chem 98: 4831–4837
36. Mei X, Wolf C (2004) Formation of new polymorphs of acridine using dicarboxylic acids as crystallization templates in solution. Cryst Growth Des 4:1099–1103
37. Metrangolo P, Resnati G (2012) Halogen bonding: where we are and where we are going. Cryst Growth Des 12:5835–5838
38. Pathak S, Kundu A, Pramanik A (2012) Regioselective synthesis of two types of highly substituted 2-pyridones through similar multicomponent reactions. Tet Lett 53:3030–3034
39. Cortez-Maya S, Cortes EC, Hernández-Ortega S et al (2012) Synthesis of 2-aminobenzophenone derivatives and their anticancer activity. Syn Comm 42:46–54
40. Allen FH (2002) The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Cryst B 58:380–388
41. Gavezzotto A (1989) On the preferred mutual orientation of aromatic groups in organic condensed media. Chem Phys Lett 161:67–72
42. Główka ML, Martynowski D, Kozłowska K (1999) Stacking of six-membered aromatic rings in crystals. J Mol Struct 474:81–89
43. Martinez CR, Iverson BL (2012) Rethinking the term “pi-stacking”. Chem Sci 3:2191–2201
44. Wheeler SE, Houk KN (2008) Substituent effects in the benzene dimer are due to direct interactions of the substituents with the unsubstituted benzene. J Am Chem Soc 130: 10854–10855
45. Pinal R (2004) Effect of molecular symmetry on melting temperature and solubility. Org Biomol Chem 2:2692–2699
46. Wei J (1999) Molecular symmetry, rotational entropy and elevated melting points. Ind Eng Chem Res 38:5019–5027
47. Brown RJC, Brown RFC (2000) Melting point and molecular symmetry. J Chem Edu 77: 724–731
48. Holler AC (1948) An observation on the relationship between the melting points of the disubstituted isomers of benzene and their chemical constitution. J Org Chem 13:70–74
49. Gavezzotti A (1995) Molecular symmetry, melting temperatures and melting enthalpies of substituted benzenes and naphthalenes. J Chem Soc Perkin Trans 2:1399–1404
50. Thalladi VR, Nüssem, Boese R (2000) The melting point alternation in α, ω-alkanedicarboxylic acids. J Am Chem Soc 122:9227–9236
51. Gopalan RS, Kumaradhas P, Kulkami GU, Rao CNR (2000) An experimental charge density study of aliphatic dicarboxylic acids. J Mol Struct 521:97–106
52. Troshina OA, Troshin PA, Peregudov AS et al (2006) Photoaddition of N-substituted piperazines to C60: an efficient approach to the synthesis of water-soluble fullerene derivatives. Chemistry 12:5569–5577
53. Fischer H, Atzpodien EA, Csato M et al (2011) In silico assay for assessing phospholipidosis potential of small druglike molecules: training, validation, and refinement using several data sets. J Med Chem 55:126–139
54. Hennequin LF, Stokes ES, Thomas AP et al (2002) Novel 4-anilinoquinazolines with C-7 basic side chains: design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J Med Chem 45:1300–1312
55. Yu T, Tagat JR, Kerekes AD et al (2010) Discovery of a potent, injectable inhibitor of aurora kinases based on the imidazo-[1,2-a]-pyrazine core. ACS Med Chem Lett 1:214–218
56. Govek SP, Oshiro G, Anzola JV et al (2010) Water-soluble PDE4 inhibitors for the treatment of dry eye. Bioorg Med Chem Lett 20:2928–2932
57. Addie M, Ballard P, Buttar D et al (2013) Discovery of 4-amino-N-[(1S)-1-(4-chlorophenyl)-3- hydroxypropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (AZD5363), an orally bioavailable, potent inhibitor of Akt kinases. J Med Chem 56:2059–2073
58. Greenwald RB, Choe YH, McGuire J, Conover CD (2003) Effective drug delivery by PEGylated drug conjugates. Adv Drug Del Rev 55:217–250
59. Zalipsky S, Gilon C, Zilkha A (1983) Attachment of drugs to polyethylene glycols. Eur Polym J 19:1177–1183
60. Smith JL, Rossiter KI, Semko CM et al (2013) PEG conjugates of potent α4 integrin inhibitors, maintaining sustained levels and bioactivity in vivo, following subcutaneous administration. Bioorg Med Chem Lett 23:4117–4119
61. Zhu GD, Arendsen DL, Gunawardana IW et al (2001) Selective inhibition of ICAM-1 and E-selectin expression in human endothelial cells. 2. Aryl modifications of 4-(aryloxy)thieno [2,3-c]pyridines with fine-tuning at C-2 carbamides. J Med Chem 44:3469–3487
62. Dossetter AG, Griffen EJ, Leach AG (2013) Matched molecular pair analysis in drug discovery. Drug Discov Today 18:724–731
63. Leach AG, Jones HD, Cosgrove DA et al (2006) Matched molecular pairs as a guide in the optimization of pharmaceutical properties; a study of aqueous solubility, plasma protein binding and oral exposure. J Med Chem 49:6672–6682
64. Zhang L, Zhu H, Mathiowetz A, Gao H et al (2011) Deep understanding of structure–solubility relationship for a diverse set of organic compounds using matched molecular pairs. Bioorg Med Chem Lett 19:5763–5770
65. Gleeson P, Bravi G, Modi S, Lowe D et al (2009) ADMET rules of thumb II: a comparison of the effects of common substituents on a range of ADMET parameters. Bioorg Med Chem 17:5906–5919
66. Hagmann WK (2008) The many roles for fluorine in medicinal chemistry. J Med Chem 51:4359–4369
67. Fujita T, Iwasa J, Hansch C (1964) A new substituent constant, π, derived from partition coefficients. J Am Chem Soc 86:5175–5180
68. Hansch C, Anderson SM (1967) The effect of intramolecular hydrophobic bonding on partition coefficients. J Org Chem 32:2583–2586
69. Bo¨hm HJ, Banner D, Bendels S et al (2004) Fluorine in medicinal chemistry. ChemBioChem 5:637–643
70. Atarashi S, Imamura M, Kimura Y (1993) Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents. J Med Chem 22:3444–3448
71. Goldberg FW, Birch AM, Leach AG et al (2013) Discovery and optimization of efficacious neutral 4-amino-6-biphenyl-7,8-dihydropyrimido[5,4-f][1, 4] oxazepin-5-one diacylglycerol acyl transferase-1 (DGAT1) inhibitors. Med Chem Comm 4:165–174
72. Jasys VJ, Lombardo F, Appleton TA et al (2000) Preparation of fluoroadamantane acids and amines: Impact of bridgehead fluorine substitution on the solution- and solid-state properties of functionalized adamantanes. J Am Chem Soc 122:466–473
73. Wenlock MC, Barton P, Luker T (2011) Lipophilicity of acidic compounds: impact of ion pair partitioning on drug design. Bioorg Med Chem Lett 21:3550–3556
74. Yokoawa F, Wang G, Chan WL et al (2013) Discovery of tetrahydropyrazolopyrimidine carboxamide derivatives as potent and orally active antitubercular agents. ACS Med Chem Lett 4:451–455
75. Scully SC, Tang AJ, Lundh M et al (2013) Small-molecule inhibitors of cytokine-mediated STAT1 signal transduction in β-cells with improved aqueous solubility. J Med Chem 56: 4125–4129
76. Cantin LD, Bayrakdarian M, Buon C et al (2012) Discovery of P2X3 selective antagonists for the treatment of chronic pain. Bioorg Med Chem Lett 22:2656–2671
77. Sheng XC, Appleby T, Butler T et al (2012) Discovery of GS-9451: an acid inhibitor of the hepatitis C virus NS3/4A protease. Bioorg Med Chem Lett 22:2629–2634
78. Kuhn B, Mohr P, Stahl M (2010) Intramolecular hydrogen-bonding in medicinal chemistry. J Med Chem 53:2601–2611
79. Sugane T, Tobe T, Hamaguchi W et al (2013) Atropisomeric 4-phenyl-4H-1,2,4-triazoles as selective glycine transporter 1 inhibitors. J Med Chem 56:5744–5756
80. Ritchie TJ, Macdonal SJF, Peace S et al (2012) The developability of heteroaromatic and heteroaliphatic rings – do some have a better pedigree as potential drug molecules than others? Med Chem Comm 3:1062–1069
81. Goldberg K, Groombridge S, Hudson J et al (2012) Oxadiazole isomers: all bioisosteres are not created equal. Med Chem Commun 3:600–604
82. Abraham MH, Duce PD, Prior DV et al (1989) Hydrogen bonding. Part 9. Solute proton donor and proton acceptor scales for use in drug design. J Chem Soc Perkin Trans II 1355–1375
83. Toulmin A, Wood JM, Kenny PW (2008) Toward prediction of alkane/water partition coefficients. J Med Chem 51:3720–3730
84. Ren F, Deng G, Wang H (2012) Discovery of novel 1,2,4-thiadiazole derivatives as potent, orally active agonists of sphingosine 1-phosphate receptor subtype 1 (S1P(1)). J Med Chem 55:4286–4296
85. Bradbury RH, Acton DG, Broadbent NL et al (2013) Discovery of AZD3514, a smallmolecule androgen receptor downregulator for treatment of advanced prostate cancer. Bioorg Med Chem Lett 23:1945–1948
86. Stepan AF, Subramanyam C, Efremov IV et al (2012) Application of the bicyclo[1.1.1]pentane motif as a nonclassical phenyl ring bioisostere in the design of a potent and orally active γ-secretase inhibitor. J Med Chem 55:3414–3424
87. Wassvik CM, Holmén AG, Draheim RI et al (2008) Molecular characteristics for solid-state limited solubility. J Med Chem 51:3035–3039
88. Etter MC (1990) Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 23:120–126
89. Abraham MH (2004) Hydrogen bond and other descriptors for thalidomide and its N-alkyl analogs; prediction of physicochemical and biological properties. Eur J Pharm Sci 21:465–469
90. Goosen C, Laing TJ, du PJ, Goosen TC, Flynn GL (2002) Physicochemical characterization and solubility analysis of thalidomide and its N-alkyl analogs. Pharm Res 19:13–19
91. Li JJ, Sutton JC, Nirschl A et al (2007) Discovery of potent and muscle selective androgen receptor modulators through scaffold modifications. J Med Chem 50:3015–3025
92. Venkatachalam TK, Zheng Y, Ghosh S, Uckun FM (2005) Structural influence on the intermolecular/intramolecular hydrogen bonding in solid state of substituted leflunomides: evidence by X-ray crystal structure. J Mol Struct 753:103–115
93. Wenglowsky S, Moreno D, Rudolph J et al (2012) Pyrazolopyridine inhibitors of B-RafV600E. Part 3: An increase in aqueous solubility via the disruption of crystal packing. Bioorg Med Chem Lett 22:912–915
94. Ishikawa M, Hashimoto Y (2011) Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry. J Med Chem 54:1539–1554
95. Paasivirta J, Sinkkonen SI (2009) Environmentally relevant properties of all 209 polychlorinated biphenyl congeners for modeling their fate in different natural and climatic conditions. J Chem Eng Data 54:1189–1213
96. Foote KM, Blades K, Cronin A et al (2013) Discovery of 4-{4-[(3R)-3-methylmorpholin-4-yl]- 6-[1-(methylsulfonyl)cyclopropyl]pyrimidin-2-yl}-1H-indole (AZ20): a potent and selective inhibitor of ATR protein kinase with monotherapy in vivo antitumor activity. J Med Chem 56:2125–2138