Studies of nonnucleoside HIV-1 reverse transcriptase inhibitors. Part 1: Design and synthesis of thiazolidenebenzenesulfonamides

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 23, 2004, Pages 6171-6182

  Masuda, Naoyuki ^a   Yamamoto, Osamu ^a   Fujii, Masahiro ^a   Ohgami, Tetsuro ^a   Fujiyasu, Jiro ^a   Kontani, Toru ^a   Moritomo, Ayako ^a   Orita, Masaya ^a   Kurihara, Hiroyuki ^a   Koga, Hironobu ^a   Nakahara, Hideaki ^a   Kageyama, Shunji ^a   Ohta, Mitsuaki ^a   Inoue, Hiroshi ^a   Hatta, Toshifumi ^a   Suzuki, Hiroshi ^a   Sudo, Kenji ^a   Shimizu, Yasuaki ^a   Kodama, Eiichi ^b   Matsuoka, Masao ^b   Fujiwara, Masatoshi ^c   Yokota, Tomoyuki ^c   Shigeta, Shiro ^d   Baba, Masanori ^e   more..

^a ASTELLAS PHARMA INC   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c Rational Drug Design Laboratories   (Japan)

^d FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

^e Grad Sch Med Dent Sci K   (Japan)

Author keywords

Benzenesulfonamide; Nonnucleoside HIV 1 reverse transcriptase inhibitor; Thiazolidene

Indexed keywords

5 ISOPROPYL 3 METHYL 2 [[(3 NITROPHENYL)SULFONYL]IMINO] 2,3 DIHYDRO 1,3 THIAZOLE 4 CARBOXYLATE; BENZENESULFONAMIDE DERIVATIVE; DELAVIRDINE; EFAVIRENZ; METHYL 5 ISOPROPYL 3 METHYL 2 [[(3 NITROPHENYL)SULFONYL]IMINO] 2,3 DIHYDRO 1,3 THIAZOLE 4 CARBOXYLATE; N (3,4 DIMETHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (3,4 DIMETHYL 5 ISOPROPYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (3,4 DIMETHYL 5 VINYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (3,4,5 TRIMETHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (4 CHLORO 5 ISOPROPYL 3 METHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (4 CYANO 5 ISOPROPYL 3 METHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (4 ISOBUTYL 5 ISOPROPYL 3 METHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (5 ACETYL 3,4 DIMETHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (5 ETHYL 3,4 DIMETHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (5 ISOPROPYL 3 METHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (5 ISOPROPYL 3 METHYL 4 TRIFLUOROMETHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (5 TERT BUTYL 3 ETHYL 4 METHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; N (5 TERT BUTYL 3,4 DIMETHYL 1,3 THIAZOL 2(3H) YLIDENE) 3 NITROBENZENESULFONAMIDE; NEVIRAPINE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

BENZENESULFONATES; BINDING SITES; DRUG RESISTANCE, VIRAL; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; MOLECULAR STRUCTURE; NEVIRAPINE; PROTEIN BINDING; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIAZOLES; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 7444224177     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.08.050     Document Type: Article

References (25)

1. M.S. Gottlieb, R. Schroff, H.M. Schanker, J.D. Weisman, P.T. Fan, R.A. Wolf, and A. Saxon N. Engl. J. Med. 305 1981 1425
2. F. Barre-Sinoussi, J.C. Chermann, F. Rey, M.T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier Science 220 1983 868
3. UNAIDS/WHO AIDS Epidemic Update, December 2003 2003 UNAIDS/WHO Geneva, Switzerland
4. R.F. Schinazi, J.R. Mead, and P.M. Feorino AIDS Res. Hum. Retroviruses 8 1992 963
5. R. Esnouf, J. Ran, C. Ross, Y. Jones, D. Stammers, and D. Stuart Nat. Struct. Biol. 2 1995 303
6. D.V. Havlir, S. Eastmen, A. Garnst, and D.D. Richman J. Virol. 70 1996 7894
7. J.P. Kleim, I. Winkler, M.A. Rosner, R. Kirsch, H. Rubsamen-Waigmann, A. Paessens, and G. Riess Virology 231 1997 112
8. D.D. Richman, D. Havlir, J. Corbeil, D. Looney, C. Ignacio, S.A. Spector, J. Sullivan, S. Cheeseman, K. Barringer, and D. Pauletti J. Virol. 68 1994 1660
9. J. Nunberg, W. Schleif, E. Boots, J. O'Brien, J. Quintero, J. Hoffman, E. Emini, and M. Goldman J. Virol. 65 1991 4887
10. L.T. Bacheler Drug Resist. Updates 2 1999 56
11. F. Bellesia J. Chem. Res. 11 1986 428
12. Wiesenfeldt, M.; Etzbach, K. H. Patent EP 450438, 1991
13. W. Schaefer, W.G. Friebe, H. Leinert, A. Mertens, T. Poll, W. Von der Saal, H. Zilch, B. Nuber, and M.L. Ziegler J. Med. Chem. 36 1993 726
14. R. Silvestri, M. Artico, G. De Martino, R. Ragno, S. Massa, R. Loddo, C. Murgioni, A.G. Loi, P. La Colla, and A. Pani J. Med. Chem. 45 2002 1567
15. V.A. Krasovskii, and S.I. Burmistrov Khim. Geterotsikl. Soedin. 1 1969 56
16. A. Andreni, M. Rambaldi, A. Leoni, R. Morigi, A. Locatelli, G. Giorgi, G. Lenaz, A. Ghelli, and E.M. Degli Eur. J. Med. Chem. 34 1999 883
17. A. Barton, S.P. Breukelman, P.T. Kaye, G.D. Meakins, and D.J. Morgan J. Chem. Soc., Perkin Trans. 1 1982 159
18. S. Harada, Y. Koyanagi, and N. Yamamoto Science 229 1985 563
19. M. Baba, S. Shigeta, S. Yuasa, H. Takashima, K. Sekiya, M. Ubasawa, H. Tanaka, T. Miyasaka, R.T. Walker, and E. De Clercq Antimicrob. Agents Chemother. 38 1994 688
20. R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, and E. De Clercq J. Virol. Methods 20 1988 309
21. A. Saitoh, H. Iwasaki, A. Nakata, A. Adachi, and H. Shinagawa Microbiol. Immunol. 34 1990 509
22. M. Baba, E. De Clercq, H. Tanaka, M. Ubasawa, H. Takashima, K. Sekiya, I. Nitta, K. Umezu, H. Nakashima, S. Mori, S. Shigeta, R.T. Walker, and T. Miyasaka Proc. Natl. Acad. Sci. U.S.A. 88 1991 2356
23. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli J. Appl. Crystallogr. 27 1994 435
24. J. Ding, K. Das, H. Moereels, L. Koymans, K. Andries, P.A. Janssen, S.H. Hughes, and E. Arnold Nat. Struct. Biol. 2 1995 405
25. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727