Novel indole-3-sulfonamides as potent HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs)

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 2, 2008, Pages 554-559

  Zhao, Zhijian ^a   Wolkenberg, Scott E ^a   Lu, Meiqing ^a   Munshi, Vandna ^a   Moyer, Gregory ^a   Feng, Meizhen ^a   Carella, Anthony V ^a   Ecto, Linda T ^a   Gabryelski, Lori J ^a   Lai, Ming Tain ^a   Prasad, Sridar G ^a   Yan, Youwei ^a   McGaughey, Georgia B ^a   Miller, Michael D ^a   Lindsley, Craig W ^a   Hartman, George D ^a   Vacca, Joseph P ^a   Williams, Theresa M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Antiviral; HIV; Indole; Sulfonamide

Indexed keywords

INDOLE 3 SULFONAMIDE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; VIRUS INHIBITION; VIRUS MUTANT;

CRYSTALLOGRAPHY, X-RAY; HIV REVERSE TRANSCRIPTASE; INDOLES; MODELS, MOLECULAR; MUTATION; REVERSE TRANSCRIPTASE INHIBITORS; SULFONAMIDES;

EID: 38149000209     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.11.085     Document Type: Article

References (18)

1. Yeni P.G., Hammer S.M., Carpenter C.C.J., Cooper D.A., Fischl M.A., Gatell J.M., Gazzard B.G., Hirsch M.S., Jacobsen D.M., Katzenstein D.A., Montaner J.S.G., Richman D.D., Saag M.S., Schechter M., Schooley R.T., Thompson M.A., Vella S., and Volberding P.A. J. Am. Med. Assoc. 288 (2002) 222
2. Palella F.J., Delaney K.M., Moorman A.C., Loveless M.O., Fuhrer J., Satten G.A., Aschman D.J., and Holmberg S.D. N. Engl. J. Med. 338 (1998) 853
3. Tarby C.M. Curr. Top. Med. Chem. 4 (2004) 1045
4. Fortin C., Joly V., and Yeni P. Expert Opin. Emerging Drugs 11 (2006) 217
5. Richman D., Havlir D., Corbeil J., Lonney D., Ignacio C., Spector S., Sullivan J., Cheeseman S., Barringer K., and Pauletti D. J. Virol. 68 (1994) 1660
6. Wei X., Ghosh S., Taylor M., Johnson V., Emini E., Deutsch P., Lifson J., Bonhoeffer S., Nowak M., Hahn B., Saag M., and Shaw G. Nature 373 (1995) 117
7. Williams T.M., Ciccarone T.M., MacTough S.C., Rooney C.S., Balani S.K., Condra J.H., Emini E.A., Goldman M.E., Greenlee W.J., Kauffman L.R., O'Brien J.A., Sardana V.V., Schleif W.A., Theoharides A.D., and Anderson P.S. J. Med. Chem. 36 (1993) 1291
8. Silvestri R., De Martino G., La Regina G., Artico M., Massa S., Vargiu L., Mura M., Loi A.G., Marceddu T., and La Colla P. J. Med. Chem. 46 (2003) 2482
9. Silvestri R., Artico M., De Martino G., La Regina G., Loddo R., La Colla M., and La Colla P. J. Med. Chem. 47 (2004) 3892
10. Silvestri R., Artico M., Bruno B., Massa S., Novellino E., Greco G., Marongiu M.E., Pani A., De Montis A., and La Colla P. Antiviral Chem. Chemother. 9 (1998) 139
11. Ragno R., Artico M., De Martino G., La Regina G., Coluccia A., Di Pasquali A., and Silvestri R. J. Med. Chem. 48 (2005) 213
12. Ragno R., Coluccia A., La Regina G., De Martino G., Piscitelli F., Lavecchia A., Novellino E., Bergamini A., Ciaprini C., Sinistro A., Maga G., Crespan E., Artico M., and Silvestri R. J. Med. Chem. 49 (2006) 3172
13. 95 is the lowest concentration of compound inhibiting replication by ≥95%.
14. Leister W., Strauss K., Wisnoski D., Zhao Z., and Lindsley C. J. Comb. Chem. 5 (2003) 322
15. Young S.D., Amblard M.C., Britcher S.F., Grey V.E., Tran L.O., Lumma W.C., Huff J.R., Schleif W.A., Emini E.E., O'Brien J.A., and Pettibone D.J. Bioorg. Med. Chem. Lett. 5 (1995) 491
16. Compounds were soaked into a pre-existing crystal of HXB2 RT containing a weakly bound efavirenz analogue. Electron density was mapped at a resolution of 2.4 Å and the structure solved by molecular replacement. PDB deposition number 2RF2.
17. Mager P.P. Drug Design Disc. 14 (1996) 241
18. Himmel D.M., Das K., Clark A.D., Hughes S.H., Benjahad A., Oumouch S., Guillemont J., Coupa S., Poncelet A., Csoka I., Meyer C., Andries K., Nguyen C.H., Grierson D.S., and Arnold E. J. Med. Chem. 48 (2005) 7582