Lysine sulfonamides as novel HIV-Protease inhibitors: Optimization of the Nε-acyl-phenyl spacer

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 24, 2003, Pages 4289-4292

  Stranix, Brent R ^a,b   Sauvé, Gilles ^a,c   Bouzide, Abderrahim ^a   Coté, Alexandre ^a   Sévigny, Guy ^a,b   Yelle, Jocelyn ^a,b  

^a Pharmacor Inc   (Canada)

^b INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

^c INRS INSTITUT ARMAND FRAPPIER   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; FUNCTIONAL GROUP; LYSINE DERIVATIVE; PHENYL GROUP; PROTEINASE INHIBITOR; SULFONAMIDE;

ACYLATION; ARTICLE; DRUG MECHANISM; DRUG SYNTHESIS; NONHUMAN; VIRUS INHIBITION;

EID: 0345358532     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.09.058     Document Type: Article

References (17)

1. Tomasselli A.G., Heinrikson R.L. Biochim. Biophys. Acta. 1477:2000;189.
2. Vella S. Handb. Exp. Pharmacol. 140:2000;23.
3. Eron J.J. Jr. Clin. Infect. Dis. 30:2000;S160.
4. Babine R., Bender S.L. Chem. Rev. 97:1997;1359.
5. Swanstrom R., Erona J. Pharmacol. Ther. 86:2000;145.
6. Marastoni M., Bortolotti F., Salvadori S., Tomatis R. Arzneim.-Forsch. 48:1998;709.
7. Marastoni M., Bazzaro M., Bortolotti F., Tomatis R. Arzneim.-Forsch. 50:2000;564.
8. Rutenber E.E., De Voss J.J., Hoffman L., Stroud R.M., Lee K.H., Alvarez J., McPhee F., Craik C., Ortiz de Montellano P.R. Bioorg. Med. Chem. 5:1997;1311.
9. Stranix, B. R.; Sauvé, G.; Bouzide, A.; Côté, A.; Bérubé, G.; Soucy, P.; Zhao, Y.; Yelle, J. US Patent No. 6,506,786; Pharmacor Inc: US, 2002.
10. Bouzide, A.; Sauvé, G.; Stranix, B. R.; Sévigny, G.; Yelle, J. US Patent No. 6,455,587; Pharmacor Inc.: US, 2002.
11. Sauve, G.; Bouzide, A. unpublished results.
12. Hiebert C.K., Kopp W.C., Richerson H.B., Barfknecht C.F. J. Med. Chem. 31:1988;2022.
13. 1H NMR showed a diastereomeric purity of greater than 95%.
14. Matayoshi E.D., Wang G.T., Krafft G.A., Erickson J. Science. 247:1990;954.
15. Japour A.J., Mayers D.L., Johnson V.A., Kuritzkes D.R., Beckett L.A., Arduino J.M., Lane J., Black R.J.P.S.R., D'Aquila R.T. Antimicrob. Agents Chemother. 37:1993;1095.
16. Pauwels R., Balzarini J., Baba M., Snoeck R., Schols D., Herdewijn P., Desmyter J., Clercq E.D. J. Virol. Methods. 20:1988;309.
17. 3 and showed an enantiomeric purity of >95%.