Virtual Darwinian drug design: QSAR inverse problem, virtual combinatorial chemistry, and computational screening

Combinatorial Chemistry and High Throughput Screening

Volumn 4, Issue 3, 2001, Pages 295-310

  De Julian Ortiz J V ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NEW DRUG;

ARTICLE; COMBINATORIAL CHEMISTRY; COMPUTER SIMULATION; DATA BASE; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VIRTUAL REALITY;

DARWINIA;

EID: 0346166647     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207013331129     Document Type: Article

References (200)

1. Balaban, A.T. J. Chem. Inf. Comput. Sci., 1985, 25, 334-343.
2. Brown, D. Mol. Diversity, 1996, 2, 217-222.
3. Apostolakis, J., Caflisch, A. Comb. Chem. High Throughput Screen., 1999, 2, 91-104.
4. a) Glasser, A.C. Methods Find. Exp. Clin. Pharmacol., 1984, 6, 563-569.
5. b) Hansch, C., Leo, A., Hoekman, D. Exploring QSAR, Hydrophobic, Electronic, and Steric Constants, ACS Professional Reference Book, American Chemical Society, Washington, DC, 1995.
6. c) Braban, M., Pop, I., Willard, X., Horvath, D. J. Chem. Inf. Comput. Sci., 2000, 40, 1119-1127.
7. Randic, M. J. Am. Chem. Soc., 1975, 97, 6609-6615.
8. Verloop, A. in Drug Design E. J. Ariëns, ed Vol III, Chapter 2, pp. 133-187. Academic Press. New York, 1972.
9. a) Bruice, T.C., Kharasch, N., Winzler, R.J. Arch. Biochem. Biophys., 1956, 305-317.
10. b) Free, S.M., Wilson, J.W. J. Med. Chem., 1964, 7, 395-402.
11. c) Bocek, K., Kopecky, J., Krivucová, M. Experientia, 1967, 23, 1038.
12. a) Mercier, C., Fabart, V., Sobel, Y., Dubois, J.E. J. Med. Chem., 1991, 34, 934-942.
13. b) Mercier, C., Sobel, Y., Dubois, J.E. Ann. Math. Chem., 1992, 3, 199-257.
14. Gutman, I., Ruscsic, B., Trinajstic, N., Wilcox, C.F. Jr. J. Chem. Phys., 1975, 62, 3399-3405.
15. Chen, J., Yang, Y., Jia, H., Lee, T. J. Math. Chem., 1994, 16, 125-136.
16. a) Randic, M., Jerman-Blazich, B., Trinajstic, N. Computers Chem., 1990, 14, 237-.
17. b) Bognanov, B., Nikolic, S., Trinajstic, N. J. Math. Chem., 1990, 5, 305-306.
18. Balaban, A.T. SAR & QSAR Environ. Res., 1998, 8, 1-21.
19. a) Pogliani, L. J. Chem. Inf. Comput. Sci., 1994, 34, 801-804.
20. b) Estrada, E. J. Chem. Inf. Comput. Sci., 1995, 35, 708-713.
21. c) Schultz, H.P., Schultz, E.B., Schultz, T.P. J. Chem. Inf. Comput. Sci., 1995, 35, 864-870.
22. d) Julián-Ortiz, J.V. de' Gregorio Alapont, C. de., Ríos-Santamarina, I., García-Domenech, R., Gálvez, J. J. Mol. Graphics Model., 1998, 16, 14-18.
23. e) Golbraikh, A., Bonchev, D., Tropsha, A. J. Chem. Inf. Comput. Sci., 2001, 41, 147-158.
24. Wiener, H. J. Am. Chem. Soc. 1947, 69, 17-20.
25. Platt, J.R. J. Chem. Phys., 1947, 15, 419-420.
26. Gordon, M., Scantlebury, G.R. Trans. Faraday Soc., 1964, 60, 605-.
27. Hosoya, H. Bull. Chem. Soc. Jpn. 1971, 44, 2332-2339.
28. Rouvray, D.H. Math. Chem., 1975, 1, 125-.
29. Balaban, A.T. Chem. Phys. Lett. 1982, 89, 399-404.
30. Bonchev, D., Trinajstic, N. J. Chem. Phys. 1977, 67, 4517-4533.
31. Trinajstic, N. Chemical Graph Theory. Vol. I , CRC Press: Boca Raton, FL, 1983.
32. Devillers, J., Balaban, A.T. Topological Indices and Related Descriptors in QSAR and QSPR, Gordon and Breach Science Publishers: Amsterdam, Nederlands. 2000.
33. a) Kier, L.B., Murray, W.J., Randic, M., Hall, L.H. J. Pharm. Sci. 1976, 65, 1226-1230.
34. b) Kier, L. B., Hall, L. H. Molecular Connectivity in Chemistry and Drug Research, Academic Press: New York, 1976.
35. a) Gozalbes, R., Julián-Ortiz, J.V. de; Antón-Fos, G.M., Gálvez, J., García-Domenech, R. Chromatographia, 2000, 51, 331-337.
36. b) Cercós-del-Pozo, R. A., Pérez-Giménez, F., Salabert-Salvador, M. T., García-March, F. J. J. Chem. Inf. Comput. Sci., 2000, 40, 178-184.
37. c) Gregorio Alapont, C. de; Kier, L. B., Hall, L. H. QSAR modeling with the electrotopological state indices: Corticosteroids. J. Comput.-Aided Mol. Design, 1998, 12, 557-561.
38. d) Ivanciuc, O; Ivanciuc, T., Balaban, A.T. J. Chem. Inf. Comput. Sci., 1998, 38, 395-401.
39. e) Pogliani, L. J. Phys. Chem., 1996,. 100, 18065-18077.
40. f) Patra, S.M., Mishra, R.K. Bull. Chem. Soc. Jpn., 1997, 70, 997-1001.
41. a) Kier, L.B., Hall, L.H. Pharm. Res., 1990, 7, 801-807.
42. b) Kier, L.B., Hall, L.H. Molecular Structure Description. The Electrotopological State, Academic Press: San Diego, 1999.
43. Galvez, J., García-Domenech, R., Salabert-Salvador, M.T., Soler, R. J. Chem. Inf. Comput. Sci., 1994, 34, 520-525.
44. a) Estrada, E., Peña, A., García-Domenech, R. J. Comput.-Aided Mol. Design, 1998, 12, 583-595.
45. b) Estrada, E. J. Chem. Inf. Comput. Sci., 1999, 39, 90-95.
46. c) Estrada, E. SAR & QSAR Environ. Res., 2000, 11, 55-73.
47. d) Estrada, E., Uriarte, E., Montero, A., Teijeira, M., Santana, L., De Clercq, E. J. Med. Chem., 2000, 43, 1975-1985.
48. e) Estrada, E., Peña A. Bioorg. Med. Chem., 2000, 8, 2755-2770.
49. Galvez, J., García-Domenech, R., Salabert-Salvador, M.T., Soler, R. J. Chem. Inf. Comput. Sci., 1995, 35, 272-284.
50. Devillers, J. Curr. Opin. Drug Discovery Develop., 2000, 3, 275-279.
51. Sternberg, M.J.E., Lewis, R.A., King, R.D., Muggleton, S. Farady Discuss., 1992, 93, 269-280.
52. a) Kubinyi, H., ed., 3D-QSAR in Drug Design. Theory. Methods. Applications, ESCOM: Leyden, 1993.
53. b) Rappé, A.K., Casewit, C.J. Molecular Mechanics Across Chemistry, University Science Books: Susalito, CA. 1997.
54. c) Veerapandian, P., ed., Structure-based drug design, Marcel Dekker: New York, 1997.
55. a) Green, S.M., Marshall, G.R. Trends Pharmacol. Sci., 1995, 16, 285-291.
56. b) Marrone, T.J., Briggs, J.M., McCammon, J.A. Annu. Rev. Pharmacol. Toxicol., 1997, 37, 71-90.
57. c) Kubinyi, H. Curr. Opin. Drug Discovery Develop., 1998, 1, 16-27.
58. d) Lemmen, C., Lengauer, T.J. Comput. Aided Mol. Des., 2000, 14, 215-232
59. a) Humlet, C., Dunbar, J.B., Jr. Annu. Rep. Med. Chem., 1993, 28, 275-284.
60. b) Doucet, J.P., Panaye, A. SAR & QSAR Environ. Res., 1997, 7, 1-24.
61. c) Lessel, U.F., Briem, H. J. Chem. Inf. Comput. Sci., 2000, 40, 246-253.
62. d) Schuffenhauer, A., Gillet, V.J., Willett, P. J. Chem. Inf. Comput. Sci., 2000, 40, 295-307.
63. a) Gilson, M.K., Given, J.A., Head, M.S. Chem. Biol., 1997, 4, 87-92.
64. b) Kubinyi, H., Folkers, G., Martin, Y.C., eds., 3D-QSAR in Drug Design. Volume 2, Kluwer Academic Publishers: Dordrecht, 1998.
65. a) Ortiz, A.R., Pisabarro, M.T., Gago, F., Wade, R.C. J. Med. Chem., 1995, 38, 2681-2691.
66. b) Pérez, C., Pastor, M., Oritiz, A.R., Gago, F. J. Med. Chem., 1998, 41, 836-852.
67. Böhm, H.-J. J. Comput.-Aided Mol. Design, 1994, 8, 243-256.
68. a) Ajay, Murcko, M.A. J. Med. Chem., 1995, 38, 4953-4967.
69. b) Bamborough, P., Cohen, F.E. Curr. Opin. Drug Struct. Biol., 1996, 6, 236-241.
70. c) Jain, A.N. J. Comput.-Aided Mol. Design, 1996, 10, 427-440.
71. d) Eldridge, M.D., Murray, C.W., Auton, T.R., Paolini, G.V., Mee, R.P. J. Comput.-Aided Mol. Design, 1997, 11, 425-445.
72. Head, R.D., Smythe, M.L., Oprea, T.I., Waller, C.L., Green, S.M., Marshall, G.R. J. Am. Chem. Soc., 1996, 118, 3959-3969.
73. a) Carbó-Dorca, R., Arnau, M., Leyda, L. Int. J. Quant. Chem., 1980, 17, 1185-1189.
74. b) Carbó-Dorca, R., Besalú, E., Amat, L., Fradera, X. J. Math. Chem., 1995, 18, 237-246.
75. c) Amat, L., Carbó-Dorca, R., Ponec, R. J. Med. Chem., 1999, 42, 5169-5180.
76. d) Carbó-Dorca, R., Robert, D., Amat, L., Gironés, X., Besalú, E. Molecular Quantum Similarity in QSAR and Drug Design. Lecture Notes in Chemistry. Vol. 73. Springer Verlag: Berlin, 2000.
77. e) Carbó-Dorca, R., Amat, L., Besalú, E., Gironés, X., Robert, D. THEOCHEM, 2000, 504, 181-228.
78. a) Cramer, R.D. III; Patterson, D.E., Bunce, J.D. J. Am. Chem. Soc., 1988, 110, 5959-5967.
79. b) Cramer, R.D. III; DePriest, S., Patterson, D.E., Hetch, P. in 3D-QSAR in Drug Design. H. Kubinyi, ed., pp. 443-485. ESCOM: Leyden, 1993.
80. Doweyko, A.M. J. Med. Chem., 1988, 31, 1396-1406.
81. Robinson, D.D., Winn, P.J., Lyne, P.D., Richards, W.G. J. Med. Chem., 1999, 42, 573-583.
82. a) Simon, Z. in 3D-QSAR in Drug Design. H. Kubinyi, ed., pp. 307-319. ESCOM: Leyden, 1993.
83. b) Sulea, T., Kurunczi, L., Oprea, T.I., Simon, Z. J. Comput. Aided Mol. Des., 1998, 12, 133-146.
84. Bravi, G., Gancia, E., Mascagni, P., Pegna, M., Todeschini, R., Zaliani, A. J. Comput. Mol. Des., 1997, 11, 79-92.
85. Walters, D.E., Hinds, R.M. J. Med. Chem., 1994, 37, 2527-2536.
86. Sagui, C., Darden, T.A. Annu. Rev. Biophys. Biomol. Struct., 1999, 28, 155-179.
87. a) Hopfinger, A.J., Wang, S., Tokarski, J.S., Jin, B., Albuquerque, M., Madhav, P.J., Duraiswami, C. J. Am. Chem. Soc., 1997, 119, 10509-10524.
88. b) Venkatarangan, P., Hopfinger, A.J. J. Chem. Inf. Comput. Sci., 1999, 39, 1141-1150.
89. Cayley, A. Philos. Mag., 1877, 3, 34.
90. Henze, H.R., Blair, C.M. J. Am. Chem. Soc., 1934, 56, 157.
91. Pólya, G. Acta Math., 1937, 68, 145.
92. Otter, R. Ann. Math., 1948, 49, 583-599.
93. a) Lederberg, J. Proc. Natl. Acad. Sci. U.S.A., 1965, 53, 134.
94. b) Lederberg, J., Sutherland, G. L., Buchanan, B. G., Feigenbaum, E. A., Robertson, A. V., Duffield, A. M., Djerassi, C. J. Am. Chem. Soc., 1969, 91, 2973-2976.
95. Randic, M. J. Chem. Phys., 1974, 60, 3920-3928.
96. a) Masinter, L.M., Sridharan, N.S., Lederberg, J., Smith, D.H. J. Am. Chem. Soc., 1974, 96, 7702-7714.
97. b) Mitrofanov, Ju.P., Raznikov, V.V., Shukurov, V.A. Zh. Anal. Khim., 1982, 37, 1477-1483.
98. c) Trinajstic N., Jericevic Z., Knop, J.V., Müller, W.R., Szymanski, K. Pure Appl. Chem., 1983, 55, 379-390.
99. d) Bangov, I.P. MATCH, 1983, 14, 235-246.
100. e) Christie, B.D., Munk, M.E. J. Chem. Inf. Comput. Sci., 1988, 28, 87-93.
101. f) Kvansnicka, V., Pospíchal, J. J. Chem. Inf. Comput. Sci., 1990, 30, 99-105.
102. g) Bangov, I.P. J. Chem. Inf. Comput. Sci., 1990, 30, 277-289.
103. h) Kerber, A., Laue, R., Moser, D. Anal. Chim. Acta, 1990, 235, 221-228.
104. i) Contreras, M.L., Valdivia, R., Rozas, R. J. Chem. Inf. Comput. Sci., 1992, 32, 323-330.
105. j) Balaban, T.S., Filip, P.A., Ivanciuc, O. J. Math. Chem., 1992, 11, 79-105.
106. k) Bytautas, L., Klein, D. J. J. Chem. Inf. Comput. Sci., 1998, 38, 1063-1078.
107. l) Ouyang, Z., Yuan, S., Brandt, J., Zheng, C. J. Chem. Inf. Comput. Sci., 1999, 39, 299-303.
108. m) Lukovits, I. J. Chem. Inf. Comput. Sci., 2000, 40, 361-366.
109. a) Carhart, R.E., Smith, D.H., Brown, H., Djerassi, C. J. Am. Chem. Soc., 1975, 97, 5755-5762.
110. b) Carhart, R.E., Smith, D.H., Gray, N.A., Nourse, J.G., Djerassi, C. J. Org. Chem., 1981, 46, 1708-1718.
111. c) Dubois, J.-E., Carabedian, M., Dagane, I. Anal. Chim. Acta, 1984, 158, 213-233.
112. d) Bremser, W., Fachinger, W. Magn. Reson. Chem., 1985, 23, 1056-1071.
113. e) Funatsu, K., Miyabayashi, N., Sasaki, S. J. Chem. Inf. Comput. Sci., 1988, 28, 18-28.
114. f) Christie, B.D., Munk, M.E. J. Chem. Inf. Comput. Sci., 1988, 28, 87-93.
115. g) Christie, B.D. Munk, M.E. J. Am. Chem. Soc., 1991, 113, 3750-3757.
116. a) Nourse, J.G. J. Am. Chem. Soc., 1979, 101, 1210-1216.
117. b) Balasubramanian, K. Theor. Chem. Acta, 1979, 51, 37-54.
118. c) Nourse, J.G., Carhart, R.E., Smith, D.H., Djerassi, C. J. Am. Chem. Soc., 1979, 101, 1216-1223.
119. d) Nourse, J.G., Smith, D.H., Carhart, R.E., Djerassi, C. J. Am. Chem. Soc., 1980, 102, 6289-6295.
120. e) Abe, H., Hayasaka, H., Miyashita, Y., Sasaki, S. J. Chem. Inf. Comput. Sci., 1984, 24, 216-219.
121. f) Zlatina, L.A; Elyashberg, M.E. MATCH, 1992, 27, 191-207.
122. g) Razinger, M., Balasubramanian, K., Perdih, M., Munk, M.E. J. Chem. Inf. Comput. Sci., 1993, 33, 812-825.
123. h) Ivanov, J., Karabunarliev, S., Mekenyan, O. J. Chem. Inf. Comput. Sci., 1994, 34, 234-243.
124. i) Contreras, M.L., Trevisiol, G.M., Alvarez, J., Arias, G., Rozas, R. J. Chem. Inf. Comput. Sci., 1999, 39, 475-482.
125. j) Bytautas, L., Klein, D. J. J. Chem. Inf. Comput. Sci., 1999, 39, 803-818.
126. k) El-Basil, S. J. Chem. Inf. Comput. Sci., 2000, 40, 572-.
127. l) Almsick, M. van Dolhaine, H., Hönig, H. J. Chem. Inf. Comput. Sci., 2000, 40, 956-966.
128. a) Bernal, J.M. Desarrollo de un nuevo método de diseño molecular asistido por ordenador. Su aplicación a fármacos betabloqueantes y benzodiazepinas. Doctoral thesis. Universitat de València (Estudi General), Spain, 1988.
129. b) Gálvez, J., García-Domenech, R., Bernal, J. M., García-March, F. J. An. Real Acad. Farm. 1991, 57, 533-546.
130. Gálvez, J., García-Domenech, R., Moliner, R., García-March, F. J. Spanish patent P9101034, 1991.
131. Gálvez, J., García-Domenech, R., Moliner, R. ; García-March, F. J. Spanish patent P9101134, 1991.
132. García-March, F. J., García-Domenech, R., Gálvez, J., Antón-Fos, G.M., Julián-Ortiz, J.V. de, Giner-Pons, R., Recio-Iglesias, C. J. Pharm. Pharmacol., 1997, 49, 10-15.
133. García-Domenech, R., García-March, F.J., Soler, R.M., Gálvez, J., Antón-Fos, G.M., Julián-Ortiz, J.V. de Quant. Struct.-Act. Relat., 1996, 15, 201-207.
134. Baskin, I.I., Gordeeva, E.V., Devdariani, R.O., Zefirov, N.S., Palyulin, V.A., Stankevich, M.I. Doklady Akad. Nauk. SSSR, 1989, 307, 613-617.
135. Faradzhev, I.A. in Algorithmic Investigations in Combinatorics. I.A. Faradzhev, ed., pp. 11-19. Nauka: Moskow, 1978.
136. a) Tratch, S.S., Lomova, O.A., Sukhachev, D.V., Palyulin, V.A., Zefirov, N.S. J. Chem. Inf. Comput. Sci., 1992, 32, 130-139.
137. b) Lomova, O.A., Sukhachev, D.V., Kumskov, M.I., Palyulin, V.A., Tratch, S.S., Zefirov, N.S. MATCH, 1992, 27, 153-174.
138. Skvortsova, M.I., Baskin, I.I., Slovokhotova, O.L., Palyulin, V.A., Zefirov, N.S. J. Chem. Inf. Comput. Sci., 1995, 35, 630-634.
139. Molchanova, M.S., Shcherbukhin, V.V., Zefirov, N.S. , J. Chem. Inf. Comput. Sci., 1996, 36, 888-899.
140. Nilakantan, R., Bauman, N., Venkataraghavan, R. J. Chem. Inf. Comput. Sci., 1991, 31, 527-530.
141. Carhart, R.E., Smith D.H., Venkataraghavan, R. J. Chem. Inf. Comput. Sci., 1985, 25, 64-73.
142. Nilakantan, R., Bauman, N., Dixon, J.S., Venkataraghavan, R. J. Chem. Inf. Comput. Sci., 1987, 27, 82-85.
143. Venkatasubramanian, V., Chan, K., Caruthers, J.M. J. Chem. Inf. Comput. Sci., 1995, 35, 188-195.
144. Milne, G.W.A. J. Chem. Inf. Comput. Sci., 1997, 37, 639-644.
145. Zheng, W., Cho, S. J., Waller, C.L., Tropsha, A. J. Chem. Inf. Comput. Sci., 1999, 39, 738-746.
146. a) Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A., Gordon, E. M. J. Med. Chem., 1994, 37, 1233-1251.
147. b) Zuckermann, R.N., Martin, E.J., Spellmeyer, D.C., Stauber, G.B., Shoemaker, K.R., Kerr J.M., Figliozzi, G.M., Goff, D.A. Siani, M.A., Simon, R.J., Banville, S.C., Brown, E.G., Wang, L., Richter, L.S., Moos, W.H. J. Med. Chem. 1994, 37, 2678-2685.
148. c) Gruber, B. J. Chem. Inf. Comput. Sci., 2000, 40, 580-587.
149. a) Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A., Gallop, M.A. J. Med. Chem. 1994, 37, 1385-1401.
150. b) Bunin, B.A., Ellmam, J.A. J. Am. Chem. Soc., 1992, 114, 10997-10999.
151. c) DeWitt, S. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913.
152. d) Bunin, B.A., Plunkett, M.J., Ellmann, J.A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4708-4712.
153. e) Plunkett, M.J., Ellmann, J.A. J. Am. Chem. Soc., 1995, 117, 3306-3307.
154. f) Murphy, M.M., Schullek, J.R., Gordon, E.M., Gallop, M.A. J. Am. Chem. Soc., 1995, 117, 7029-7030.
155. g) Thompson, L.A., Ellman, J.A. Chem. Rev., 1996, 96, 555-600.
156. h) Kurth, M.J., Randall, L.A.A., Takenouchi, K. J. Org. Chem., 1996, 61, 8755-8761.
157. i) Sim, M.M., Lee, Ch.L., Ganesan, A. J. Org. Chem, 1997, 62, 9358-9360.
158. j) Warr, W.A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140.
159. a) Bures, M.G., Martin, Y.C. Curr. Opin. Chem. Biol., 1998, 2, 376-380.
160. b) Bayada, D.M., Hamersma, H., Geerestein, V.J. van J. Chem. Inf. Comput. Sci., 1999, 39, 1-10.
161. c) Leach, A.R., Bradshaw, J., Green, D.V.S., Hann, M.M., Delany, J.J. III J. Chem. Inf. Comput. Sci., 1999, 39, 1161-1172.
162. d) Matter, H., Pötter, T. J. Chem. Inf. Comput. Sci., 1999, 39, 1211-1225.
163. e) Darvas, F., Dormán, G., Papp, Á. J. Chem. Inf. Comput. Sci., 2000, 40, 314-322.
164. f) Pickett, S.D., McLay, I.M., Clark, D.E. J. Chem. Inf. Comput. Sci., 2000, 40, 263-272.
165. g) Martin, E., Wong, A. J. Chem. Inf. Comput. Sci., 2000, 40, 215-220.
166. h) Stanton, R.V., Mount, J., Miller, J.L. J. Chem. Inf. Comput. Sci., 2000, 40, 701-705.
167. i) Agrafiotis, D.K., Lobanov, V.S. J. Chem. Inf. Comput. Sci., 2000, 40, 1030-1038.
168. j) Gorse, D., Lahana, R. Curr. Opin. Chem. Biol., 2000, 4, 287-294.
169. Martin, E.J., Blaney, J.M., Siani, M.A., Spellmeyer, D.C., Wong, A.K., Moos, W.H. J. Med. Chem., 1995, 38, 1431-1436.
170. Brown, R.D., Martin, Y.C. J. Chem. Inf. Comput. Sci., 1996, 36, 572-584.
171. Hassan, M., Bielawski, J.P., Hempel, J.C., Waldman, M. Mol. Diversity, 1996, 2, 64-74.
172. Wang, J., Ramnarayan, K. J. Comb. Chem., 1999, 1, 524-533.
173. Kirkpatrick, D.L., Watson, S., Ulhaq, S. Comb. Chem. High Throughput Screen., 1999, 2, 211-221.
174. Hopfinger, A.J., Reaka, A., Venkatarangan, P., Duca, J.S., Wang, S. J. Chem. Inf. Comput. Sci., 1999, 39, 1151-1160. Baxter, C.A,; Murray, C.W., Waszkowycz, B., Li, J., Sykes, A., Bone, R.G.A., Perkins, T.D.J., Wylie, W. J. Chem. Inf. Comput. Sci., 2000, 40, 254-262.
175. Hopfinger, A.J., Reaka, A., Venkatarangan, P., Duca, J.S., Wang, S. J. Chem. Inf. Comput. Sci., 1999, 39, 1151-1160. d) Baxter, C.A,; Murray, C.W., Waszkowycz, B., Li, J., Sykes, A., Bone, R.G.A., Perkins, T.D.J., Wylie, W. J. Chem. Inf. Comput. Sci., 2000, 40, 254-262.
176. a) Sheridan, R.P., Kearsley, S.K. J. Chem. Inf. Comput. Sci., 1995, 35, 310-320.
177. b) Zheng, W., Cho, S.J., Tropsha, A. J. Chem. Inf. Comput. Sci., 1998, 38, 251-258.
178. c) Cho, S.J., Zheng, W., Tropsha, A. J. Chem. Inf. Comput. Sci., 1998, 38, 259-268.
179. Li, J., Murray, Ch.W., Waszkowycz, B., Young, S.C. Drug Discovery Today, 1998, 3, 105-112.
180. Grassy, G., Calas, B., Yasri, A., Lahana, R., Woo, J., Iyer, S., Kaczorek, M., Floc'h, R., Buelow, R. Nature Biotechnol., 1998, 16, 748-752.
181. Klopman, G., Raychandhury, C. J. Chem. Inf. Comput. Sci., 1990, 30, 12-19.
182. Kier, L.B., Hall, L.H., Frazer, J.W. J. Chem. Inf. Comput. Sci., 1993, 33, 143-147.
183. Kier, L.B., Hall, L.H., Frazer, J.W. J. Chem. Inf. Comput. Sci., 1993, 33, 148-152.
184. Hall, L.H., Dailey, R.S., Kier, L.B. J. Chem. Inf. Comput. Sci., 1993, 33, 598-603.
185. Kier, L.B., Hall, L.H. Quant. Struct.-Act. Relat., 1993, 12, 383-388.
186. Kvasniecka, V., Pospíchal, J. J. Chem. Inf. Comput. Sci., 1996, 36, 516-526.
187. Metropolis, M., Rosenbluth, A.W., Rosenbluth, M.N., Teller, A.: Teller, E. J. Chem. Phys., 1953, 21, 1087-1092.
188. Kvasnicka, V., Pospíchal, J. J. Math. Chem., 1992, 9, 181-196.
189. Julián-Ortiz, J.V. de,Gálvez, J., Muñoz-Collado, C., García-Domenech, R., Gimeno-Cardona, C. J. Med. Chem., 1999, 42, 3308-3314.
190. a) Mekenyan, O., Bonchev, D., Balaban, A.T. J. Math. Chem., 1988, 2, 347-375.
191. b) Diudea, M. V., Kacsó, I. E. MATCH, 1991, 26, 255-269.
192. a) Kuntz, I.D., Blaney, J.M., Oatley, S.J., Langridge, R., Ferrin, T.E. J. Mol. Biol., 1982, 161, 269-288.
193. b) Moon, J.B., Howe, W.J. Proteins: Struct. Func. Genet., 1991, 11, 314-328.
194. c) Nishibata, Y., Itai, A. Tetrahedron, 1991, 47, 8985-8990.
195. d) Lawrence, M.C., Davis, P.C. Proteins: Struct. Func. Genet., 1992, 12, 31-41.
196. e) Verlinde, C.L.M.J., Rudenko, G., Hol, W.G.J. J. Comput.-Aided Mol. Design, 1992, 6, 131-147.
197. g) Rotstein, S.H., Murcko, M.A. J. Med. Chem., 1993, 36, 1700-1710.
198. Nishibata, Y., Itai, A. J. Med. Chem., 1993, 36, 2921-1928.
199. a) Böhm, H.-J. J. Comput.-Aided Mol. Design, 1992, 6, 61-78.
200. b) Böhm, H.-J. J. Comput.-Aided Mol. Design, 1996, 10, 265-272.