Prediction of Physicochemical Properties

Virtual Screening for Bioactive Molecules

Volumn 10, Issue , 2008, Pages 33-58

  Morris, Jeff J ^a   Bruneau, Pierre P ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Coefficient; Drugs; High throughput screening (HTS); Physical properties

Indexed keywords

COEFFICIENT; DRUGS; HIGH-THROUGHPUT SCREENING; PHYSICOCHEMICAL PROPERTY;

PHYSICAL PROPERTIES;

EID: 84956748673     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527613083.ch3     Document Type: Chapter

References (113)

1. D. E. Leahy. J. Lynch, D.C. Taylor, in Novel Drug Delivery and its Therapeutic Implications, Prestcott, Nimmo (Eds.), John Wiley, Chichester 1989, pp. 33-44.
2. W. M. Pardridge, D. Triguero, J. Yang, P. Cancilla J. Pharmacol. Exp. Ther. 1990, 253. 884-891.
3. D. A. Smith, in Computer Assisted Lead Finding and Optimisation. Wiley-VCH, 1997, pp. 265-277.
4. D. E. Leahy, J. J. Morris, P.J. Taylor, A.R. Wait, J. Chem. Soc. Perk. Trans. 2 1992, 723-731.
5. C. Hansch, A. Leo, in Exploring QSAR Fundamentals and Applications in Chemistry and Biology, A.C.S. Washington, D.C. 1995. Pomona or MedChem logP Database; available from Daylight CIS or BioByte.
6. Pomona or MedChem logP Database; available from Daylight CIS or BioByte.
7. A. J. Leo, Chem. Rev. 1993, 93, 1281-1306.
8. G. L. Biagi, M. Recanatini, A. M. Barbara, P. A. Borea, Process Control and Quality 1997, 10,129-149.
9. A. J. Leo, Methods and Principles in Medicinal Chemistry Vol 4. (Lipophilicity in Drug Action and Toxicology), V. Pliska, B. Testa, H. Van de Waterbeemd (Eds.), VCH Weinheim, Cambridge 1996, pp 157-172.
10. R. Mannhold, R. Rekker, The Calculation of Drug Lipophilicity, VCH, Weinheim 1992.
11. P.-A. Carrupt, B. Testa, Rev. Compul. Chem. 1997, 241-315.
12. CLOGP v 4.61. DAYLIGHT CIS, 27401 Los Altos Suite 360 Mission Viego, CA 92691.
13. A. J. Leo, 217th ACS Meeting Anaheim Ca Book of Abstracts 1999, 105.
14. A. K. Ghose, A. Pritchett, G. M. Crippen, J. Comp. Chem. 1988, 9, 80-90.
15. P. Broto, G. Moreau, C. Vandyke, Eur. J. Med. Chem. 1984,19,71-78.
16. PrologP Compudrug Chemistry Ltd, 1362 Budapest, POB 405, Hungary.
17. Advanced Chemical Development Inc., 133 Richmond Street West, Suite 605, Toronto, Ontario, Canada M5H 2L3.
18. G. O Spessard, J. Chem. Inf. Compul. Sci. 1998,38, 1250-1253.
19. A. K. Ghose, V. Viswananadhan, J. Wendoloski, J. Phys. Chem. B 1998,102, 3762-3772.
20. S. A. Wildman, G. M. Crippen, J. Chem. Inf. Compul. Sci. 1999,39, 868-873.
21. SMARTS Toolkit v. 4.6 DAYLIGHT CIS, 27401 Los Altos Suite 360 Mission Viego, CA 92691.
22. R. Wang, Y. Fu, L. Lai, J. Chem. Inf. Compul. Sci. 1997,37,615-621.
23. J. Devillers, D. Domine, C. Guillon, W. Karcher, J. Pharm. Sci. 1998,87,1086-1090.
24. J. Devillers, Analusis 1999,27,23-29.
25. L. B. Kier, L. W Hall, Molecular Structure Description. The Electrotopological State, Academic Press, San Diego 1999.
26. J. J. Huuskonen, A. E. P Villa, I. V. Tetko, J. Pharm. Sci. 1999,88, 229-233.
27. K.-J. Schaper, M. Samitier, Quant. Struct. Act. Relat. 1997,16, 224-230.
28. M. H. Abraham, Chem. Soc. Rev. 1993,22, 73-83.
29. M. H. Abraham, H. Chadha, in Lipophilicity in Drug Action and Toxicology, V. Pliska, B.Testa (Eds.),VCH, Weinheim 1996.
30. P. Politzer, J. S. Murray, Theoretical and Computational Chemistry 1994,1 (Quantitative Treatment of Solute/Solvent Interactions), JA'i-lW.
31. J. S. Murray, P. Politzer, G. R. Famini, J. Mol. Struct. (Theochem.) 1998,454,299-306.
32. J. Platts, D. Butina, M. H. Abraham, A. Hersey, J. Chem. Inf. Compul. Sci. 1999,39,835-845.
33. G. Klopman, J.-Y. Li, M.Dimayuga, J. Chem. Inf. Comput. Sci. 1994,34,752-781.
34. Breindle, B. Beck, T. Clark, R.C. Glen, J. Mol. Model. 1997,3,142-145.
35. G. D. Hawkins, D. A. Liotard, C. J. Cramer, D. G. Truhlar, J. Org. Chem., 1998, 63, 4305-4313.
36. C. J. Cramer, D. G. Truhlar, Chem. Rev. 1999, 99, 2161-2200.
37. H. van de Waterbeemd, R. Mannhold, Methods and Principles in Medicinal Chemistry Vol4, (Lipophilicity in Drug Action and Toxicology), V. Pliska, B. Testa, H. Van de Waterbeemd (Eds), VCH Weinheim, Cambridge 1996, pp 401-108.
38. R. Mannhold, R. Rekker, C. Sonntag, A. M. TerLaak, K. Dross, E. Polymeropoulis, J. Pharm. Sci. 1995,84, 1410-1419.
39. J. Devillers, D. Domine, SAR QSAR Env. Res. 1997, 7,195-232.
40. J. J. Morris, A. R. Wait, unpublished observations.
41. I. Moriguchi, S. Hirono, I. Nakagome, H. Hirano, Chem. Pharm. Bull. 1994,42, 976-978.
42. A. Leo, Chem. Pharm. Bull. 1995, 43,512-513.
43. C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997,23,3-25.
44. P. Gaillard, P. A. Carrupt, B. Testa, A. J. Boudon, J. Comput.-Aided Mol. Design 1994, 8, 83-96.
45. R. C. Young, R. C. Mitchell, T. H Brown, C. R. Ganellin, R. Griffiths, M. Jones, K. R. Rana, D. Saunders, I. R. Smith, N. R. Sore. T. J. Wilks, J. Med. Chem. 1988,31,656-671.
46. R. H. Davies, R. D. Bagnall, W. G. M. Jones, Int. J. Quantum Chem. Quantum Biol. Symp. 1974, 7,201-212.
47. M. H. Abraham, J. Platts, A. Hersey, A. J. Leo, R. W. Taft, J. Pharm. Sci., in press.
48. F. Csizmadia, A. Tsantili-Kakoulidou, I. Panderi, F. Darvas, J. Pharm. Sci. 1997,86, 865-870.
49. A. Tsantili-Kakoulidou, I. Panderi, F. Csizmadia, F. Darvas, J. Pharm Sci. 1997,86,1173-1179.
50. S. H. Yalkowsky, S. Bannerjee, Aqueous Solubility, Methods of Estimation for Organic Com-pounds, Marcel Dekker, New York 1992.
51. M. H. Abraham, J. Le, J. Pharm. Sci. 1999, 88, 868-880.
52. F. Irmann, Chem. Ing. Tech. 1965,37, 789-798.
53. K. Wakita, M. Yoshimoto, S. Miyamoto, H. Watanabe, Chem. Pharm. Bull. 1986,34, 4663-681.
54. T. Suzuky, J. Comput. Aided Mol. Design 1991, 5,149-166.
55. D. Tiegs, J. Gmehling, P. Ramussen, A. Fredenslund, Ind. Eng. Chem. Res. 1987,26,159-161.
56. A. Kan, M. B. Tomson, Environ. Sci. Technol. 1996,30, 1369-1376.
57. P. B. Myrdal, A. M. Manka, S. H. Yalkowsky, Chemosphere 1995,30, 1619-1637.
58. Y. C. Lee, P. B. Myrdal, S. H. Yalkowsky, Chemosphere 1996,33, 2129-2144.
59. Y. C. Lee, S. Pinssuwan, S. H. Yalkowsky, Chemosphere 1997,35, 775-782.
60. G. Klopman, S. Wang, D. M. Balthasar, J. Chem. Inf. Comput. Sci. 1992,32,474-482.
61. C. Hansch, J. E. Quinlan, G. L. Lawrence, J. Org. Chem. 1968,33, 347-350.
62. J. Hilderbrand, R. Scott, Regular Solutions, Prentice Hall, Englewood Cliffs, N.J. 1962.
63. W. M. Meylan, P. H. Howard, R. S. Boethling, Env. Toxicol. Chem. 1996,15,100-106.
64. J. Nouwen, B.Hansen, Quant. Struct. Act. Relat. 1996,15, 17-30.
65. P. Bruneau, unpublished observations.
66. J. J. Morris, A. R. Wait, unpublished observations.
67. A. R. Katritzky, U. Maran, M. Karelson, V. S. Lobanov, J. Chem. Inf. Comput. Sci. 1997, 31, 913-919.
68. R-M. Dannenfelser, S. H. Yalkowsky, J. Pharm. Sci. 1999,88,722-724.
69. P. Ruelle, U. W. Kesselring, J. Pharm. Sci. 1998,87, 987-997.
70. P. Ruelle, U. W. Kesselring, J. Pharm. Sci. 1998,87, 998-1014.
71. E. Silla, I. Tunon, F. Villar, J. L Pascual-Ahuir, J. Mol. Struct. (Theochem.) 1992, 254, 369-377.
72. N. Bodor, A. Harget, M.-J. Huang, J. Am. Chem. Soc. 1991,113,9480-9483.
73. N. Bodor, M.-J. Huang, A. Harget, Int. J. Quantum Chem. Quantum Chem. Symp. 1992, 26, 853-867.
74. N. Bodor, M.-J., Huang, J. Pharm. Sci. 1992, 81, 954-960.
75. J. M. Sutter, P. C. Jurs, J. Chem. Inf. Comput. Sci. 1996,36,100-107.
76. B. E. Mitchell, P.C. Jurs, J. Chem. Inf. Comput. Sci. 1998,38,489-496.
77. A. R. Katritzky, Y. Wang, S. Sild, T. Tamm, M. Karelson, J. Chem. Inf. Comput. Sci. 1998, 38, 720-725.
78. J. Huuskonen, M. Salo, J. Taskinen, J. Pharm. Sci. 1997,86,450-454.
79. J. Huuskonnen, M. Salo, J. Taskinen, J. Chem. Inf. Comput. Sci. 1998,38,450-456.
80. B. Lucie, N. Trinajstic, S. Sild, M. Karlson, A. R. Katritzky, J. Chem. Inf. Comput. Sci. 1999, 39, 610-621.
81. G. Klopman, Quant. Struct. Act. Relat. 1992,11,176-184.
82. G. Klopman, D. Fercu, J. Comp. Chem. 1994,15,1041-1050.
83. L. P. Hammett, Physical Organic Chemistry, McGraw-Hill, N.Y., 1970.
84. M. Charton, Prog. Phys. Org. Chem. 1980,13,119-251.
85. C.Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91,165-195.
86. D.D. Perrin, B. Dempsey, E. P. Serjeant, pA'a Prediction for Organic Acids and Bases, Chapman and Hall, London 1981.
87. P. J. Taylor, A. R. Wait, J. Chem. Soc. Perk Trans 2,1986,1765-1770.
88. E.P. Serjeant, B. Dempsey, lonisation constants of Organic Acids in Aqueous Solution, Pergamon, London 1979.
89. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London 1965.
90. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution Supplement, Butter-worths, London 1972.
91. C.Hansch, A. Leo, D. Hoekman, Exploring QSAR Hydrophobic Electronic and Steric Constants, ACS Washington, 1995.
92. F.Csizmadia, J. Szegezdi, F. Darvas, Proc. 9"' European Symposium on Structure-Activity Relationships: QSAR and Molecular Modelling, C. G Wermuth (Ed.), ESCOM, Leiden 1993, pp 507-510.
93. S. H. Hilal, L. A. Carreira, S. W. Karrickhoff, in Theoretical and Computational Chemistry, P. Politzer, J. S. Murray (Eds.), Elsevier Science, 1994, pp. 291-353.
94. S. H. Hilal, S. W. Karickhoff, Quant. Struct. Act. Relat. 1995,14, 348-355.
95. S. H. Hilal, Y. El-Shabrawy, L. A. Carreira, S. W. Karickhoff, S. S. Toubar, M. Rizk, Talanta 1996, 43, 607-619.
96. K. H. Kim, Y. C. Martin, J. Med. Chem. 1991,34, 2056-2060.
97. S. L. Dixon, P. Jurs, J. Comput. Chem. 1993,14,1460-1467.
98. F. Herve, S. Urien, E. Albengres, J.-C. Duche, J.-P. Tillement, Clin. Pharmacokinet. 1994, 26, 44-58.
99. R. Kaliszan, A. Nasal, M. Turowski, Biomedical Chromatography 1995, 9, 211-215.
100. R. Olsom, D. Christ, Ann. Rep. Med. Chem. 1996,31, 327-336.
101. S. Sugio, A. Kashima, S. Mochizuki, M. Noda, K. Kobayashi, Protein Engineering 1999, 12, 439-446.
102. S. Curry, H. Mandelkow, P. Brick, N. Franks, Nature Struct. Biol. 1998,5, 827-834.
103. D.C. Carter, J. X. Ho, Adv. Prot. Chem. 1994,45,153-203.
104. J. M. Vandenbelt, C. Hansh, C. Church, J. Med. Chem. 1972,15,787-789.
105. W. Scholtan, Arzneimittelforschung 1968,18,505-517.
106. C. Hansch, A. Leo, in Exploring QSAR Fundamentals and Applications in Chemistry and Biolo-gy, A.C.S. Washington, D.C. 1995, pp. 226-227.
107. F.Desmotes-Mainard, F. Pehourcq, A. Radouane, L. Labat, B. Bannwarth, Pharm. Res. 1995,12, 1535-1538.
108. L. Deschamps-Labat, F. Pehourcq, M. Jagou, B. Bannwarth, J. Pharm. Biomed. Anal. 1997, 76, 223-229.
109. A. Nasal, A. Radwanska, K. Osmialowski, A. Bucinski, R. Kaliszan, G. Barker, P. Sun, R. Hartwick, Biomedical Chromatography 1994, 8, 125-129.
110. R. Kaliszan, A. Nasal, M. Turowski, Biomedical Chromatography 1995, 9,211-215.
111. G.Zlotos, A. Bucker, M. Kinzig-Schippers, F. Sorgel, U. Holzgrabe, J. Pharm. Sci. 1998, 87, 215-220.
112. A. Wait, unpublished results.
113. S. C. Valvani, S. H. Yalkowsky, T. J. Roseman J. Pharm. Sci. 1981, 70, 502-507.