Anticancer and antiviral sulfonamides

Current Medicinal Chemistry

Volumn 10, Issue 11, 2003, Pages 925-953

  Scozzafava, Andrea ^a   Owa, Takashi ^b   Mastrolorenzo, Antonio ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b EISAI CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 CHLOROSULFAQUINOXALINE; ACETAZOLAMIDE; ALKYLATING AGENT; AMPRENAVIR; ANTIDIABETIC AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; COLCHICINE; DIURETIC AGENT; ETHOXZOLAMIDE; FUROSEMIDE; GLIBENCLAMIDE; INDISULAM; INTEGRASE INHIBITOR; MATRIX METALLOPROTEINASE; METHAZOLAMIDE; N [2 [(4 HYDROXYPHENYL)AMINO] 3 PYRIDINYL] 4 METHOXYBENZENESULFONAMIDE; NUCLEOSIDE DERIVATIVE; PROTEINASE INHIBITOR; RNA DIRECTED DNA POLYMERASE INHIBITOR; SULFATHIAZOLE; SULFONAMIDE; SULFONE DERIVATIVE; SULOFENUR; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE; VINCRISTINE;

ANGIOGENESIS; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CANCER; CANCER INHIBITION; CELL CYCLE G1 PHASE; CLINICAL TRIAL; COMPUTER AIDED DESIGN; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG MECHANISM; DRUG RESISTANCE; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IN VITRO STUDY; IN VIVO STUDY; MICROTUBULE ASSEMBLY; NONHUMAN; NUCLEOTIDE SEQUENCE; PHENOTYPE; PROTEIN MOTIF; RETROVIRUS; REVIEW; SIDE EFFECT; STRUCTURE ACTIVITY RELATION; TUMOR GROWTH; UNINDEXED SEQUENCE; VIRUS INHIBITION; VIRUS MUTATION; VIRUS REPLICATION;

ANIMALS; ANTI-HIV AGENTS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CLINICAL TRIALS; DRUG DESIGN; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 0013209248     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033457647     Document Type: Review

References (165)

1. Buolamwini, J.K. Curr. Opin. Chem. Biol. 1999, 3, 500-509.
2. Lehnert, M. Eur. J. Cancer 1996, 6, 912-920.
3. Loo, T.W.; Clarke, D.M. J. Natl. Cancer Inst. 2000, 92, 898-902.
4. Condra, J.H.; Miller, M.D.; Hazuda, D.J.; Emini, E.A. Annu. Rev. Med. 2002, 53, 541-555.
5. Drew, J. Science 2000, 287, 1960-1964.
6. Owa, T.; Nagasu, T. Exp. Opin. Ther. Patents 2000, 10, 1725-1740.
7. Supuran, C.T.; Scozzafava, A. Exp. Opin. Ther. Patents 2000, 10, 575-600.
8. Supuran, C.T.; Scozzafava, A. Exp. Opin. Ther. Patents 2002, 12, 217-242.
9. Supuran, C.T.; Scozzafava, A. Med. Res. Rev. 2003, 23, 146-189.
10. Boyd, A.E. Diabetes 1988, 37, 847-850.
11. Thornber, C.W. Chem. Soc. Rev. 1979, 8, 563-580.
12. Ogden, R.C.; Flexner, C.W., Eds. Protease Inhibitors in AIDS Therapy. Marcel Dekker: New York, Basel, 2001.
13. Supuran, C.T.; Scozzafava, A.; Mastrolorenzo, A. Exp. Opin. Ther. Patents 2001, 11, 221-259;
14. Supuran, C.T.; Scozzafava, A.; Clare, B.W. Med. Res. Rev. 2002, 22, 329-372.
15. Scozzafava, A.; Supuran, C.T. J. Med. Chem. 2000, 43, 3677-3687.
16. Wouters, J.; Michaux, C.; Durant, F.; Dogné, J.M.; Delarge, J.; Masereel, B. Eur. J. Med. Chem. 2000, 35, 923-929.
17. Chegwidden, W.R.; Spencer, I.M.; Supuran, C.T. The roles of carbonic anhydrase isozymes in cancer. In Gene Families: Studies of DNA, RNA, Enzymes and Proteins, Xue, G.; Xue, Y.; Xu, Z.; Hammond, G.L.; Lim, H.A. Eds., World Scientific, Singapore, 2001, pp. 157-169.
18. Kaluz, S.; Kaluzova, M.; Opavsky, R.; Pastorekova, S.; Gibadulinova, A.; Dequiedt, F.; Kettmann, R.; Pastorek, J. J. Biol. Chem. 1999, 274, 32588-32595.
19. Pastorek, J.; Pastorekova, S.; Callebaut, I.; Mornon, J.P.; Zelnik, V.; Opavsky, R.; Zatovicova, M.; Liao, S.; Portetelle, D.; Stanbridge, E.J.; Zavada, J.; Burny, A.; Kettmann, R. Oncogene 1994, 9, 2877-2888.
20. Pastorekova, S.; Parkkila, S.; Parkkila, A.K.; Opavsky, R.; Zelnik, V.; Saarnio, J.; Pastorek, J. Gastroenterology 1997, 112, 398-408.
21. Tureci, O.; Sahin, U.; Vollmar, E.; Siemer, S.; Gottert, E.; Seitz, G.; Parkkila, A.K.; Shah, G.N.; Grubb, J.H.; Pfreundschuh, M.; Sly, W.S. Proc. Natl. Acad. Sci. USA 1998, 95, 7608-7613.
22. Karhumaa, P.; Parkkila, S.; Tureci, O.; Waheed, A.; Grubb, J.H.; Shah, G.; Parkkila, A.; Kaunisto, K.; Tapanainen, J.; Sly, W.S.; Rajaniemi, H. Mol. Hum. Reprod. 2000, 6, 68-74.
23. Mori, K.; Ogawa, Y.; Ebihara, K.; Tamura, N.; Tashiro, K.; Kuwahara, T.; Mukoyama, M.; Sugawara, A.; Ozaki, S.; Tanaka, I.; Nakao, K. J. Biol. Chem. 1999, 274, 15701-15705.
24. Ivanov, S.V.; Kuzmin, I.; Wei, M.H.; Pack, S.; Geil, L.; Johnson, B.E.; Stanbridge, E.J.; Lerman, M.I. Proc. Natl. Acad. Sci. USA 1998, 95, 12596-12601.
25. Kaneta, S.; Ishizuki, S,; Kasahara, M.; Nagao, S.; Takahashi, H. Exp. Anim., 1999, 48, 161-169;
26. Nishimori, I.; Fujikawa-Adachi, K.; Onishi, S.; Hollingsworth, M.A. Ann. N. Y.Acad. Sci. 1999, 880, 5-16.
27. Saarnio, J.; Parkkila, S., Parkkila, A.K., Pastorekova, S., Haukipuro, K., Pastorek, J., Juvonen, T., Karttunen, T.J. J. Hepatol. 2001, 35, 643-649;
28. Giatromanolaki, A., Koukourakis, M.I., Sivridis, E., Pastorek, J., Wykoff, C.C., Gatter, K.C., Harris, A.L. Cancer Res. 2001, 61, 7992-7998;
29. Chia, S.K., Wykoff, C.C., Watson, P.H., Han, C., Leek, R.D., Pastorek, J., Gatter, K.C., Ratcliffe, P., Harris, A.L. J. Clin. Oncol. 2001, 19, 3660-3668.
30. Teicher, B.A.; Liu, S.D.; Liu, J.T.; Holden, S.A.; Herman, T.S. Anticancer Res. 1993, 13, 1549-1556.
31. Chegwidden, W.R.; Spencer, I.M. Inflammopharmacol. 1995, 3, 231-239.
32. Parkkila, S.; Rajaniemi, H.; Parkkila, A.K.; Kivela, J.; Waheed, A.; Pastorekova, S.; Pastorek, J.; Sly, W.S. Proc. Natl. Acad. Sci. USA 2000, 97, 2220-2224.
33. Supuran, C.T.; Scozzafava A. Eur. J. Med. Chem. 2000, 35, 867-874.
34. Supuran, C.T.; Scozzafava, A. J. Enzyme Inhib. 2000, 15, 597-610.
35. Scozzafava, A.; Supuran, C.T. Bioorg. Med. Chem. Lett. 2000, 10, 1117-1120.
36. Supuran, C.T.; Briganti, F.; Tilli, S.; Chegwidden, W.R.; Scozzafava, A. Bioorg. Med. Chem. 2001, 9, 703-714.
37. Branda R.F.; McCormack J.J.; Perlmutter, C.A. Biochem. Pharmacol. 1988, 37, 4557-4564.
38. Fisherman, J.S.; Osborn, B.L.; Chun, H.G. Invest. New Drugs 1993, 11, 1-9.
39. Rigas J.R.; Francis, P.A.; Miller, V.A.; Tong W.P.; Roistacher, N.; Kris M.G.; Orazem J.P.; Young C.W.; Warrell R.P. Jr. Cancer Chemother. Pharmacol. 1995, 35, 483-488.
40. Miller, V.A.; Rigas, J.R.; Tong, W.P.; Reid, J.R.; Pisters,.K.M.; Grant, S.C.; Heelan, R.T.; Kris, M.G. Cancer Chemother. Pharmacol. 1997, 40, 415-418.
41. Yoshino H.; Ueda N., Niijima J., Sugumi H., Kotake Y., Koyanagi N.; Yoshimatsu K., Asada M., Watanabe T., Nagasu T., Tsukahara K., Iijima A., Kitoh K. J. Med. Chem. 1992, 35, 2496-2497.
42. Yoshimatsu, K.; Yamaguchi, A.; Yoshino H.; Koyanagi N.; Kitoh K. Cancer Res. 1997, 57, 3208-3213.
43. Koyanagi, N.; Nagasu, T.; Fujita, F.; Watanabe, T.; Tsukahara, K.; Funahashi, Y.; Fujita, M.; Taguchi, T.; Yoshino, H.; Kitoh, K. Cancer Res. 1994, 54, 1702-1706.
44. Yamamoto, K.; Noda, K.; Yoshimura, A.; Fukuoka, M.; Furuse, K.; Niitani, H. Cancer Chemother. Pharmacol. 1998, 42, 127-134.
45. Gwaltney, S.L. II, Imade, H.M.; Li, Q.; Gehrke, L.; Credo, R.B.; Warner, R.B.; Le, J.Y.; Kovar, P.; Frost, D.; Ng, S.C.; Sham, H.L. Bioorg. Med. Chem. Lett. 2001, 11, 1671-1673;
46. Tanaka, H.; Ohshima, N.; Hidaka, H. Proc. Am. Assoc. Cancer Res. New Orleans, USA 1998, 39, Abstract 2180.
47. Ueda, N.; Tsukahara, N.; Watanabe, T.; Haneda, T.; Kotake, Y.; Niijima, J.; Nagasu, T.; Yoshimatsu, K.; Yoshino, H.; Koyanagi, N.; Kitoh, K. Proc. Am. Assoc. Cancer Res. Toronto, Canada 1995, 36, Abstract 2290.
48. Owa T.; Okauchi, T.; Yoshimatsu, K.; Hata Sugi, N.; Ozawa, Y.; Nagasu, T.; Koyanagi N., Okabe, T.; Kitoh K.; Yoshino, H. Bioorg. Med. Chem. Lett. 2000, 10, 1223-1226;
49. Owa T.; Yoshino, H.; Okauchi, T.; Okabe, T.; Ozawa, Y.; Hata Sugi, N.; Yoshimatsu, K.; Nagasu, T.; Koyanagi N.; Kitoh K. Bioorg. Med. Chem. Lett. 2002, 12, 2097-2100.
50. Owa T.; Yoshino H., Okauchi T., Yoshimatsu K., Ozawa Y., Sugi N.H., Nagasu T., Koyanagi N., Kitoh K. J. Med. Chem. 1999, 42, 3789-3799.
51. Ozawa, Y.; Funahashi, Y.; Senba, T.; Sonoda, J.; Yoshimatsu, K. Proc. Am. Assoc. Cancer Res. San Diego, USA 1997, 38, Abstract 3163;
52. Ozawa, Y.; Sugi, N.H.; Nagasu, T.; Owa, T.; Watanabe, T.; Koyanagi, N.; Yoshino, H.; Kitoh, K.; Yoshimatsu, K. Eur. J. Cancer 2001, 37, 2275-2282.
53. Fukuoka, K.; Usuda, J.; Iwamoto, Y.; Fukumoto, H.; Nakamura, T.; Yoneda, T.; Narita, N.; Saijo, N.; Nishio, K. Invest. New Drugs 2001, 19, 219-227;
54. Owa, T.; Yokoi, A.; Yoshimatsu, K.; Nagasu, T.; Miller, L.; Ravic, M. Proc. AACR-NCI-EORTC International Conference, Molecular Targets and Cancer Therapeutics: Discovery, Biology, and Clinical Applications. Miami Beach, USA 2001, Abstract 697;
55. Yokoi, A.; Kuromitsu, J.; Kawai, T.; Nagasu, T.; Sugi, N.H.; Yoshimatsu, K.; Yoshino, H.; Owa, T. Mol. Cancer Ther. 2002, 1, 275-286;
56. Owa, T.; Yokoi, A.; Yamazaki, K.; Yoshimatsu, K.; Yamori, T.; Nagasu, T. J. Med. Chem. 2002, 45, 4913-4922.
57. Dittrich, C.; Dumez, H.; Calvert, H.; Hanauske, A.R.; Ravic, M.; Faber, M.; van Houten, T.; Wanders, J.; Fumoleau, P. Proc. Am. Assoc. Cancer Res. San Francisco, USA 2000, 41, Abstract 3875;
58. Droz, J.P.; Roche, H.; Zanetta, S.; Terret, C.; Blay, J.Y.; Dumortier, A.; Kroon, K.; Wanders, J.; Ravic, M.; Fumoleau, P. Proc. Am. Assoc. Cancer Res. San Francisco, USA 2000, 41, Abstract 3876;
59. Punt, C.J.A.; Fumoleau, P.; Walle, B.V.D.; Deporte-Fety, R.; Bourcier, C.; Faber, M.; Ravic, M.; Wagener, D.J.T. Proc. Am. Assoc. Cancer Res. San Francisco, USA 2000, 41, Abstract 3877;
60. Punt, C.J.; Fumoleau, P.; van de Walle, B.; Faber, M.N.; Ravic, M.; Campone, M. Ann. Oncol. 2001, 12, 1289-1293;
61. Raymond, E.; Huinink, W.T.B.; Taieb, J.; Beijnen, J.H.; Mekhaldi, S.; Kroon, K.; Wanders, J.; Ravic, M.; Fumoleau, P.; Ducreux, M.; Escudier, B.; Armand, J.P. Proc. Am. Assoc. Cancer Res. San Francisco, USA 2000, 41, Abstract 3889.
62. Howbert, J.J., Grossman, C.S., Crowell, T.A., Rieder, B.J., Harper, R.W., Kramer, K.E., Tao, E.V., Aikins, J., Poore, G.A., Rinzel, S.M.; Grindey, G.B.; Shaw, W.N.; Todd, G. J. Med. Chem. 1990, 33, 2393-2407.
63. Mohamadi, F., Specs, M.M., Grindey, G.B. J. Med. Chem. 1992, 35, 3012-3016.
64. Toth, J.E., Grindey, G.B., Ehlhardt, W.J., Ray, J.E., Boder, G.B., Bewley, J.R., Klingerman, K.K., Gates, S.B., Rinzel, S.M., Schultz, R.M., Weir, L.C., Worzalla, J.F. J. Med. Chem. 1997, 40, 1018-1025.
65. Chern, J.W.; Leu, Y.L.; Wang, S.S.; Jou, R.; Lee, C.F.; Tsou, P.C.; Hsu, S.C.; Liaw, Y.C.; Lin, H.M. J. Med. Chem. 1997, 40, 2276-2286.
66. Rush, G.F., Rinzel, S.M., Boder, G., Heim, R.A., Toth, J.E., Ponsler, G.D. Biochem. Pharmacol. 1992, 44, 2387-2394.
67. Sosinski, J., Thakar, J.H., Germain, G.S., Dias, P., Harwood, F.C., Kuttesch, J.F., Houghton, P.J. Mol. Pharmacol. 1994, 45, 962-970.
68. Houghton, P.J., Houghton, J.A. Invest. New Drugs 1996, 14, 271-280.
69. Ehlhardt, W.J. Drug Metab. Dispos. 1991, 19, 370-375.
70. Phelps, P.C.; Jain, P.T.; Berezeski, I.K.; Boder, G.B.; Trump, B.F. Cancer Lett. 1995, 88, 27-35.
71. Mooré D.J.; Reust, T. J. Bioenerg. Biomembr. 1997, 29, 281-289.
72. Houghton, P.J.; Sosinski, J.; Thakar, J.H.; Boder, G.B.; Grindey, G.B. Biochem. Pharmacol. 1995, 49, 661-668.
73. Houghton, P.J.; Cheshire, P.J.; Myers, L. Anti-Cancer Drugs 1995, 6, 317-323.
74. Houghton, P.J.; Houghton, J.A.; Myers, L.; Cheshire, P.J.; Howbert, J.J.; Grindey, G.B. Cancer Chemother. Pharmacol. 1989, 25, 84-88.
75. Taylor, C.W.; Alberts, D.S.; Ketcham, M.A. J. Clin. Oncol. 1989, 7, 1733-1740.
76. Armand, J.P.; Recondo, G.; Gouyette, A. Invest. New Drugs 1989, 7, 423-428.
77. Diab, S.G.; Hilsenbeck, S.G.; Izbicka, E.; Weitman, S.D.; Von Hoff, D.D. Anti-Cancer Drugs 1999, 10, 303-307.
78. Park Choo, H.Y.; Lim, J.S.; Kam, Y.; Yeon Kim, S.; Lee,.J. Eur. J. Med. Chem. 2001, 36, 829-836.
79. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Exp. Opin. Ther. Patents, 2001, 11, 765-787;
80. Scozzafava, A.; Casini, A.; Supuran, C.T. Curr. Med. Chem., 2002, 9, 1167-1185.
81. Medina, J.C.; Shan, B.; Beckmann, H.; Farrell, R.P.; Clark, D.L.; Learned, R.M.; Roche, D.; Li, A.; Baichwal, V.; Case, C.; Baeuerle, P.A.; Rosen, T.; Jaen, J.C. Bioorg. Med. Chem. Lett. 1998, 8, 2653-2656.
82. Medina, J.C.; Roche, D.; Shan, B.; Learned, R.M.; Frankmoelle, W.P.; Clark, D.L.; Rosen, T.; Jaen, J.C. Bioorg. Med. Chem. Lett. 1999, 9, 1843-1846.
83. Shan, B.; Medina, J.C.; Santha, E.; Frankmoelle, W.P.; Chou, T.C.; Learned, R.M.; Narbut, M.R.; Scott, D.; Wu, P.; Jaen, J.C.; Rosen, T.; Timmermans, P.B.M.; Beckmann, H. Proc. Natl. Acad. Sci. USA 1999, 96, 5686-5691.
84. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Bioorg. Med. Chem. Lett. 2000, 10, 1887-1891.
85. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. J. Enzyme Inhib. 2001, 16, 55-64.
86. Flygare, J.; Medina, J.C.; Shan, B.; Clark, D.L.; Rosen, T. WO Patent 1998, 05315.
87. Woessner, J.F.; Nagase, H. Matrix metalloproteinases and TIMPs. Oxford Univ. Press, Oxford, 2000, pp. 1-223.
88. Supuran, C.T.; Scozzafava, A. Matrix metalloproteinases (MMPs). In Proteinase and Peptidase Inhibition: Recent Potential Targets for Drug Development. Smith, H.J.; Simons, C. Eds., Taylor & Francis Publishing House, London and new York, 2002, pp. 35-61.
89. MacPherson, L.J.; Bayburt, E.K.; Capparelli, M.P.; Carroll, B.J.; Goldstein, R.; Justice, M.R.; Zhu, L.; Hu, S.; Melton, R.A.; Fryer, L.; Goldberg, R.L.; Doughty, J.R.; Spirito, S.; Blancuzzi, V.; Wilson, D.; O'Byrne, E.M.; Ganu, V.; Parker, D.T. J. Med. Chem. 1997, 40, 2525-2532
90. Whittaker, M., Floyd, C.D., Brown, P. Gearing, A.J.H. Chem. Rev. 1999, 99, 2735-2776.
91. Scozzafava, A.; Supuran, C.T. Protease inhibitors. J. Med. Chem. 2000, 43, 1858-1865
92. Clare, B.W., Scozzafava, A.; Supuran, C.T. J. Med. Chem. 2001, 44, 2253-2258.
93. Smith, H.J.; Nicholls, P.J.; Simons, C.; Le Lain, R. Exp. Opin. Ther. Patents 2001, 11, 789-824.
94. Pasqualini, J.R.; Chetrite, G.; Nestour, E.L. J. Endocrinol. 1996, 150, S99-S105.
95. Li, P.K.; Chugh, G.H.; Guo, J.P.; Peters, A.; Selcer, K.W. Steroids 1998, 63, 425-432.
96. Briganti, F.; Scozzafava, A.; Supuran, C.T. Eur. J. Med. Chem. 1997, 32, 901-910.
97. Woo, L.W.; Howarth, N.M.; Purohit, A.; Hejaz, H.A.; Reed, M.J.; Potter, B.V. J. Med. Chem. 1998, 41, 1068-1083.
98. Li, P.K.; Selcer, K.W. WO Patent 2000, 18397.
99. Meinke, P.T.; Liberator, P Curr. Med. Chem. 2001, 8, 211-235.
100. Gray, S.G.; Ekstrom, T.J. Exp. Cell Res. 2001, 262, 75-83;
101. Mahlknecht, U.; Hoelzer, D.; Mol. Med. 2000, 6, 623-644.
102. Owa, T.; Yoshino, H.; Yoshimatsu, K.; Nagasu, T. Curr. Med. Chem. 2001, 8, 1487-1503.
103. Lavoie, R.; Bouchain, G.; Frechette, S.; Woo, S.H.; Khalil, E.A.; Leit, S.; Fournel, M.; Yan, P.T.; Trachy-Bourget, M.C.; Beaulieu, C.; Li, Z.; Besterman, J.; Delorme, D. Bioorg. Med. Chem. Lett. 2001, 11, 2847-2850.
104. Pomarnacka, E.; Kornicka, A. Farmaco 2001, 56, 571-577.
105. Brzozowski, Z.; Saczewski, F. J. Med. Chem. 2002, 45, 430-437.
106. Bramson, H.N.; Corona, J.; Davis, S.T.; Dickerson, S.H.; Edelstein, M.; Frye, S.V.; Gampe, R.T.; Harris, P.A.; Hassel, A.; Holmes, W.D.; Hunter, R.N.; Lackey, K.E.; Lovejoy, B.; Luzzio, M.J.; Montana, V.; Rocque, W.J.; Rusnak, D.; Shewchuk, L.; Veal, J.M.; Walker, D.H.; Kuyper, L.F. J. Med. Chem. 2001, 44, 4339-4358.
107. Supuran, C.T.; Scozzafava, A.; Casini, A. Med. Res. Rev. 2003, 23, 146-189.
108. Abadoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morère, A.; Montero, J.L. Bioorg. Med. Chem. 1996, 4, 1227-1235;
109. Huang, Z.; Lin, Z.; Huang, J. Eur. J. Med. Chem. 2001, 36, 863-872.
110. Chibale, K.; Ojima, I.; Haupt, H.; Geng, X.; Pera, P.; Bernacki, R.J. Bioorg. Med. Chem. Lett. 2000, 10, 2457-2460.
111. de Clercq, E. Curr. Med. Chem. 2001, 8, 1543-1572.
112. Erickson, J.W. HIV-1 protease as a target for AIDS therapy. In Protease inhibitors in AIDS therapy, Ogden, R.C.; Flexner, C.W. Eds., Marcel Dekker, New York, 2001, pp. 1-25.
113. Tung, R.D.; Livingston, D.J.; Rao, B.G.; Kim, E.E.; Baker, C.T., Boger, J.S.; Chambers, S.P.; Deininger, D.D.; Dwyer, M.; Elsayed, L.; Fulghum, J.; Li, M.; Murcko, M.A.; Navia, M.A.; Novak, P.; Pazhanisamy, S.; Stuver, C.; Thomson, J.A. Design and synthesis of amprenavir, a novel HIV protease inhibitor. In Protease inhibitors in AIDS therapy, Ogden, R.C.; Flexner, C.W. Eds., Marcel Dekker, New York, 2001, pp. 101-118.
114. Gatell, J.M. J. HIV Ther. 2001, 6, 95-99.
115. Casini, A.; Scozzafava, A.; Supuran, C.T. Exp. Opin. Ther. Patents 2002, 12, 1307-1327.
116. Rusconi, S.; La Seta Catamancio, S. Expert Opin. Investig. Drugs 2002, 11, 387-395.
117. Ghosh, A.K.; Shin, D.; Swanson L. Farmaco 2001, 56, 29-32.
118. De Meyer, S.; Azijn, H.; van Ginderen, M.; de Baere, I.; Pauwels, S.; De Bethune, M.P. Antiviral Ther. 2002, 7, S5.
119. Chrusciel, R.A.; Thaisrivongs, S.; Nicholas, J.A. HIV protease inhibitors in early development. Protease inhibitors in AIDS therapy, Ogden, R.C.; Flexner, C.W. Eds., Marcel Dekker, New York, 2001, pp. 119-137.
120. Wlodawer, A.; Gustchina, A. Biochim. Biophys. Acta 2000, 1477, 16-34.
121. Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157-162.
122. Turner, S.R.; Strohbach, J.W.; Tommasi, R.A.; Aristoff, P.A.; Johnson, P.D.; Skulnick, H.I.; Dolak, L.A.; Seest, E.P.; Tomich, P.K.; Bohanon, M.J.; Horng, M.M.; Lynn, J.C.; Chong, K.T.; Hinshaw, R.R.; Watenpaugh, K.D.; Janakiraman, M.N.; Thaisrivongs, S. J. Med. Chem. 1998, 41, 3467-3476.
123. Skulnick, H.I.; Johnson, P.D.; Aristoff, P.A.; Morris, J.K.; Lovasz, K.D.; Howe, W.J.; Watenpaugh, K.D.; Janakiraman, M.N.; Anderson, D.J.; Reischer, R.J.; Schwartz, T.M., Banitt, L.S.; Tomich, P.K.; Lynn, J.C.; Horng, M.M.; Chong, K.T.; Hinshaw, R.R.; Dolak, L.A.; Seest, E.P.; Schwende, F.J.; Rush, B.D.; Howard, G.M.; Toth, L.N.; Wilkinson, K.R.; Kakuk, T.J.; Johnson, C.W.; Cole, S.L.; Zaya, R.M.; Zipp, G.L.; Possert, P.L.; Dalga, R.J.; Zhong, W.Z.; Williams, M.G.; Romines, K.R. J. Med. Chem. 1997, 40, 1149-1164.
124. Lee, Y.S.; Lee, Y.S.; Lee, J.Y.; Kim, S.N.; Lee, C.K.; Park, H. Bioorg. Med. Chem. Lett. 2000, 10, 2625-2627.
125. Dorsey, B.D.; Vacca, J.P. Discovery and early development of indinavir. In Protease inhibitors in AIDS therapy, Ogden, R.C.; Flexner, C.W. Eds., Marcel Dekker, New York, 2001, pp. 65-83.
126. Hulten, J.; Bonham, N.M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Aqvist, J.; Classon, B.; Danielson, U.H.; Karlen, A.; Kvarnstrom, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885-897.
127. Backbro, K.; Lowgren, S.; Osterlund, K.; Atepo, J.; Unge, T.; Hulten, J.; Bonham, N.M.; Schaal, W.; Karlen, A.; Hallberg, A. J. Med. Chem. 1997, 40, 898-902.
128. Hulten, J.; Andersson, H.O.; Schaal, W.; Danielson, U.H.; Classon, B.; Kvarnstrom, L; Karlen, A.; Unge, T.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1999, 42, 4054-4061.
129. Choy, N.; Choi, H.; Jung, W.H.; Kim, C.R.; Yoon, H.; Kim, S.C.; Lee, T.G.; Koh, J.S. Bioorg. Med. Chem. Lett. 1997, 7, 2635-2638.
130. Borthwick, A.D.; Crame, A.J.; Ertl, P.F.; Exall, A.M.; Haley, T.M.; Hart, G.J.; Mason, A.M.; Pennell, A.M.K.; Singh, O.M.P.; Weingarten, G.G.; Woolven, J.M. J. Med. Chem. 2002, 45, 1-18.
131. Ilies, M.A.; Scozzafava, A.; Supuran, C.T. Exp. Opin. Ther. Patents 2002, 12, 1181-1214.
132. Shieh, H.S.; Kurumbail, R.G.; Stevens, A.M.; Stegeman, R.A.; Sturman, E.J.; Pak, J.Y.; Witwer, A.J.; Palmier, M.O.; Wiegand, R.C.; Holwerda, B.C.; Stallings, W.C. Nature 1996, 383, 279-282.
133. De Clercq, E. J. Pharmacol. Exptl. Ther. 2001, 297, 1-10.
134. De Clercq, E. Nature Drug Discov. 2002, 1, 13-25.
135. Andrews, C.W.; Chan, J.H.; Freeman, G.A.; Romines, K.R.; Tidwell, J.H. WO Patent 2001, 17982.
136. Selvam, P.; Chandramohan, M.; De Clercq, E.; Witvrouw, M.; Pannecouque, C. Eur. J. Pharm. Sci. 2001, 14, 313-316.
137. Arranz, E.; Dìaz, J.A.; Ingate, S.T.; Witvrouw, M.; Pannecouque, C.; Balzarini, J.; De Clercq, E.; Vega, S. Bioorg. Med. Chem. 1999, 7, 2811-2822.
138. Corbett, J.W.; Gearhart, L.A.; Ko, S.S.; Rodgers, J.D.; Cordova, B.C.; Klabe, R.M.; Erickson-Viitanen, S.K. Bioorg. Med. Chem. Lett. 2000, 10, 193-195.
139. Pommier, Y.; Neamati, N. Adv. Virus Res. 1999, 52, 427-458.
140. Neamati, N. Exp. Opin. Invest. Drugs 2001, 10, 281-296.
141. Neamati, N.; Mazumder, A.; Zhao, H.; Sunder, S.; Burke, T.R.; Schultz, R.J.; Pommier, Y. Antivir. Chem. Chemother. 1997, 8, 385-393.
142. Chen, I.J.; Neamati, N.; Nicklaus, M.C.; Orr, A.; Anderson, L.; Barchi, J.J.; Kelley, J.A.; Pommier, Y.; MacKerell, A.D. Bioorg. Med. Chem. 2000, 8, 2385-2398.
143. Goldkur, Y.; Craigie, R.; Cohen, G.H.; Fujiwara, T.; Yoshinaga, T.; Fujishita, T.; Sugimoto, H.; Endo, T.; Murai, H.; Davies, D.R. Proc. Natl. Acad. Sci. USA 1999, 96, 13040-13043.
144. Neamati, N.; Mazumder, A.; Sunder, S.; Owen, J.M.; Schultz, R.J.; Pommier, Y. 2- Antivir. Chem. Chemother. 1997, 8, 485-495.
145. Rice, W.G.; Schaeffer, C.A.; Harten, B.; Villinger, F.; South, T.L.; Summers, M.F.; Henderson, L.E.; Bess, J.W. Jr; Arthur, L.O.; McDougal, J.S. Nature 1993, 361, 473-475.
146. Rice, W.G.; Supko, J.G.; Malspeis, L.; Buckheit, R.W. Jr; Clanton, D.; Bu, M.; Graham, L.; Schaeffer, C.A.; Turpin, J.A.; Domagala, J. Science 1995, 270, 1194-1197.
147. Mely, Y.; Cornille, F.; Fournie-Zaluski, M.C.; Darlix, J.L.; Roques, B.P.; Gerard, D. Biopolymers 1991, 31, 899-906.
148. Ramboarina, S.; Moreller, N.; Fournie-Zaluski, M.C.; Roques, B.P. Biochemistry 1999, 38, 9600-9607.
149. Loo, J.A.; Holler, T.P.; Sanchez, J.; Gogliotti, R.; Maloney, L.; Reily, M.D. J. Med. Chem. 1996, 39, 4313-4320.
150. Domagala, J.M.; Bader, J.P.; Gogliotti, R.D.; Sanchez, J.P.; Stier, M.A.; Song, Y.; Prasad, J.V.; Tummino, P.J.; Scholten, J.; Harvey, P.; Holler, T.; Gracheck, S.; Hupe, D.; Rice, W.G.; Schultz, R. Bioorg. Med. Chem. 1997, 5, 569-579.
151. Huang, M.; Maynard, A.; Turpin, J.A.; Graham, L.; Janini, G.M.; Covell, D.G.; Rice, W.G. J. Med. Chem. 1998, 41, 1371-1381.
152. Turpin, J.A.; Song, Y.; Inman, J.K.; Huang, M.; Wallqvist, A.; Maynard, A.; Covell, D.G.; Rice, W.G.; Appella, E. J. Med. Chem. 1999, 42, 67-86.
153. Basrur, V.; Song, Y.; Mazur, S.J.; Higashimoto, Y.; Turpin, J.A.; Rice, W.G.; Inman, J.K.; Appella, E. J. Biol. Chem. 2000, 275, 14890-14897.
154. Tomaras, G.D.; Greenberg, M.L. Curr. Infect. Dis. Rep. 2001, 3, 93-99.
155. Blair, W.S.; Lin, P.F.; Meanwell, N.A.; Wallace, O.B. Drug. Dev. Today 2000, 5, 183-194.
156. Mastrolorenzo, A.; Scozzafava, A.; Supuran, C.T. Exp. Opin. Ther. Patents, 2001, 11, 1245-1252;
157. Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. J. Enz. Inhib. Med. Chem. 2002, 17, 69-76.
158. Kwong, P.D.; Wyatt, R.; Robinson, J.; Sweets, R.W.; Sodroski, J.; Hendrickson W.A. Nature 1998, 393, 648-659.
159. Stantchev, T.S.; Broder, C.C. Cytokine Growth Factors Rev. 2001, 12, 219-243;
160. fernandez, E.J.; Lolis, E. Annu. Rev. Pharmacol. Toxicol. 2002, 42, 469-499.
161. Root, M.J.; Kay, M.S.; Kim, P.S. Science 2001, 291, 884-888.
162. Dorn, C.; Finke, P.E.; Oates, B.; Budhu, R.J.; Mills, S.G.; MacCoss, M.; Malkowitz, L.; Springer, M.S.; Daugherty, B.L.; Gould, S.L.; DeMartino, J.A.; Siciliano, S.J.; Carella, A.; Carver, G.; Holmes, K.; Danzeisen, R.; Hazuda, D.; Kessler, J.; Lineberger, J.; Miller, M.; Schleif, W.A.; Emini, E.A. Bioorg. Med. Chem. Lett. 2001, 11, 259-264.
163. Finke, P.E.; Meurer, L.C.; Oates, B.; Mills, S.G.; MacCoss, M.; Malkowitz, L.; Springer, M.S.; Daugherty, B.L.; Gould, S.L.; DeMartino, J.A.; Siciliano, S.J.; Carella, A.; Carver, G.; Holmes, K.; Danzeisen, R.; Hazuda, D.; Kessler, J.; Lineberger, J.; Miller, M.; Schleif, W.A.; Emini, E.A. Bioorg. Med. Chem. Lett. 2001, 11, 265-270.
164. Kim, D.; Wang, L.; Caldwell, C.G.; Chen, P.; Finke, P.E.; Oates, B.; MacCoss, M.; Mills, S.G.; Malkowitz, L.; Gould, S.L.; DeMartino, J.A.; Springer, M.S.; Hazuda, D.; Miller, M.; Kessler, J.; Danzeisen, R.; Carver, G.; Carella, A.; Holmes, K.; Lineberger, J.; Schleif, W.A.; Emini, E.A. Bioorg. Med. Chem. Lett. 2001, 11, 3103-3106.
165. Willoughby, C.A.; Berk, S.C.; Rosauer, K.G.; Degrado, S.; Chapman, K.T.; Gould, S.L.; Springer, M.S.; Malkowitz, L.; Schleif, W.A.; Hazuda, D.; Miller, M.; Kessler, J.; Danzeisen, R.; Holmes, K.; Lineberger, J.; Carella, A.; Carver, G.; Emini, E.A. Bioorg. Med. Chem. Lett. 2001, 11, 3137-3141.