Diarylsulfones, a novel class of human immunodeficiency virus type 1 integrase inhibitors

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 2, 1997, Pages 385-393

  Neamati, Nouri ^a   Mazumder, Abhijit ^a   Zhao, He ^a   Sunder, Sanjay ^a   Burke Jr , Terrence R ^a   Schultz, Robert J ^a   Pommier, Yves ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CURCUMIN; DAPSONE; ENZYME INHIBITOR; INTEGRASE; NSC 107159; NSC 122653; NSC 155173; NSC 156750; NSC 176305; NSC 186265; NSC 291628; NSC 291629; NSC 30176; NSC 374413; NSC 38049; NSC 39859; NSC 633001; NSC 646122; NSC 689416; NSC 689437; NSC 85650; NSC 85651; QUERCETAGETIN; SALAZOSULFAPYRIDINE; SULFANILAMIDE DERIVATIVE; SULFONE DERIVATIVE; TYRPHOSTIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ASSAY; HELPER CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PRIORITY JOURNAL; VIRUS REPLICATION;

EID: 0031046693     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.2.385     Document Type: Article

References (30)

1. Artico, M., R. Silvestri, S. Massa, A. G. Loi, S. Corrias, P. Giovanna, and P. L. Colla. 1996. 2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones. J. Med. Chem. 39:522-530.
2. Burke, Jr., T. R., M. R. Fesen, A. Mazumder, J. Wang, A. M. Carothers, G. Grunberger, J. Driscoll, K. W. Kohn, and Y. Pommier. 1995. Hydroxylated aromatic inhibitors of HIV-1 integrase. J. Med. Chem. 38:4171-4178.
3. Carteau, S., J. F. Mouscadet, H. Goulanuic, F. Subra, and C. Auclair. 1993. Inhibitory effect of the polyanionic drug suramin on the in vitro HIV DNA integration reaction. Arch. Biochem. Biophys. 305:606-610.
4. Chow, S. A., K. A. Vincent, V. Ellison, and P. O. Brown. 1992. Reversal of integration and DNA splicing mediated by integrase of human immunodeficiency virus. Science 255:723-726.
5. Cushman, M., W. M. Golebiewski, Y. Pommier, A. Mazumder, D. Reymen, E. De Clerq, L. Graham, and W. G. Rice. 1995. Cosalane analogs with enhanced potencies as inhibitors of HIV-1 protease and integrase. J. Med. Chem. 38:443-452.
6. De Benedetti, P. G. 1991. Molecular modeling and quantitative structure-activity analysis of antibacterial sulfanilamides and sulfones. Prog. Drug Res. 36:361-417.
7. De Benedetti, P. G. 1987. Structure-activity relationships and mechanism of action of antibacterial sulphanilamides and sulfones. Adv. Drug Res. 16:227-279.
8. De Clercq, E. 1995. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38:2491-2517.
9. Fesen, M., Y. Pommier, F. Leteurtre, S. Hiroguchi, J. Yung, and K. W. Kohn. 1994. Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem. Pharmacol. 48:595-608.
10. Hong, Y.-L., P. A. Hossler, D. H. Calhoun, and S. T. Meshnick. 1995. Inhibition of recombinant pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob. Agents Chemother. 39:1756-1763.
11. Katz, R. A., and A. M. Skalka. 1994. The retroviral enzymes. Annu. Rev. Biochem. 63:133-173.
12. LaFemina, R. L., P. L. Graham, K. LeGrow, J. C. Hastings, A. Wolfe, S. D. Young, E. A. Emini, and D. J. Hazuda. 1995. Inhibition of human immunodeficiency virus integrase by bis-catechols. Antimicrob. Agents Chemother. 39:320-324.
13. Liehr, J. G., and D. Roy. 1990. Free radical generation by redox cycling of estrogens. Free Radical Biol. Med. 8:415-423.
14. Lopez de Compadre, R. L., R. A. Pearlstein, A. J. Hopfinger, and J. K. Seydel. 1987. A quantitative structure-activity relationship analysis of some 4-aminodiphenyl sulfone antibacterial agents using linear free energy and molecular modeling methods. J. Med. Chem. 30:900-906.
15. Matsukawa, T., B. Ohta, and T. Imada. 1950. Syntheses of sulfide and sulfone compounds. III. Syntheses of diphenyl sulfone compounds. J. Pharm. Soc. Jpn. 70:77-80.
16. Mazumder, A., K. Raghavan, J. Weinstein, K. W. Kohn, and Y. Pommier. 1995. Inhibition of human immunodeficiency virus type-1 integrase by curcamin. Biochem. Pharmacol. 49:1165-1170.
17. Mazumder, A., A. Gazit, A. Levitzki, M. Nicklaus, J. Yung, G. Kohlhagen, and Y. Pommier. 1995. Effects of tyrphostins, protein kinase inhibitors, on human immunodeficiency virus type 1 integrase. Biochemistry 34:15111-15122.
18. Mazumder, A., N. Neamati, J.-P. Sommadossi, G. Gosselin, R. F. Schinazi, J.-L. Imbach, and Y. Pommier. 1996. Effects of nucleotide analogs on human immunodeficiency virus integrase. Mol. Pharmacol. 49:621-628.
19. Mazumder, A., S. Wang, N. Neamati, M. Nicklaus, S. Sunder, J. Chen, G. W. A. Milne, W. G. Rice, T. R. Burke, Jr., and Y. Pommier. 1996. Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease. J. Med. Chem. 39:2472-2481.
20. McMahon, J. B., R. J. Gulakowski, O. S. Weislow, R. J. Schultz, V. L. Narayanan, D. J. Clanton, R. Pedemonte, F. W. Wassmundt, R. W. Buckheit, Jr., W. D. Decker, E. L. White, J. P. Bader, and M. R. Boyd. 1993. Diarylsulfones, a new chemical class of nonnucleoside antiviral inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 37:754-760.
21. Mironov, G. S., V. V. Vetrova, and M. I. Farberov. 1969. Synthesis of diaryl sulfones and polycarboxylic acids based on them. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 12:1588-1593.
22. Mouscadet, J. F., S. Carteau, H. Goulaouic, F. Subra, and C. Auclair. 1994. Triplex-mediated inhibition of HIV DNA integration in vitro. J. Biol. Chem. 269:21635-21638.
23. Neamati, N., P. Sunthankar, A. Mazumder, N. King, S. D. Hume, Y. Pommier, and R. R. Drake. Proteolytic mapping identification of the azidothymidine monophosphate binding site of human immunodeficiency virus type-1 integrase. Submitted for publication.
24. Pommier, Y., G. Kohlhagen, K. W. Kohn, F. Leteurtre, M. C. Wani, and M. E. Wall. 1995. Interaction of an alkylating camptothecin derivative with a DNA base at topoisomerase I-DNA cleavage sites. Proc. Natl. Acad. Sci. USA 92:8861-8865.
25. Prajapati, S. P., J. H. Pardanani, and S. Sethna. 1977. Studies on 4,4′-dihydroxydiphenyl sulfone and 4,4′-dihydroxydiphenyl ether. J. Indian Chem. Soc. 54:971-974.
26. Rice, P., R. Craigie, and D. R. Davies. 1996. Retroviral integrases and their cousins. Curr. Opin. Struct. Biol. 6:76-83.
27. Rice, W. G., and J. P. Bader. 1995. Discovery and in vitro development of AIDS antiviral drugs as biopharmaceuticals. Adv. Pharmacol. 33:389-138.
28. Stanwell, C., B. Ye, S. H. Yuspa, and T. R. Burke, Jr. 1996. Cell protein cross-linking by erbstatin and related compounds. Biochem. Pharmacol. 52: 475-480.
29. Weislow, O. W., R. Kiser, D. Fine, J. Bader, R. H. Shoemaker, and M. R. Boyd. 1989. New soluble-formazan assay for HIV-1 cytopathic effects: application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Inst. 81:577-586.
30. Zhao. H., N. Neamati, A. Mazumder, S. Sunder, Y. Pommier, and T. R. Burke, Jr. Arylamide inhibitors of HIV-1 integrase. J. Med. Chem. Submitted for publication.