Synthesis and Antiviral Activity of New Anti-HIV Amprenavir Bioisosteres

Starting from the chemical structure of the recent FDA-approved anti-HIV drug Amprenavir (Agenerase), a potent HIV-protease inhibitor, we have designed new series of Amprenavir bioisoteres in which the methylene group of the benzyl group was replaced by a sulfur atom. This structural modification ha...

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Veröffentlicht in:Journal of medicinal chemistry 2002-07, Vol.45 (15), p.3321-3324
Hauptverfasser: Rocheblave, Luc, Bihel, Frédéric, De Michelis, Céline, Priem, Ghislaine, Courcambeck, Jérôme, Bonnet, Brice, Chermann, Jean-Claude, Kraus, Jean-Louis
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Sprache:eng
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Zusammenfassung:Starting from the chemical structure of the recent FDA-approved anti-HIV drug Amprenavir (Agenerase), a potent HIV-protease inhibitor, we have designed new series of Amprenavir bioisoteres in which the methylene group of the benzyl group was replaced by a sulfur atom. This structural modification has required an original multistep synthesis. Unfortunately, introduction of the sulfur atom abolished or drastically decreased both inhibitory activity on recombinant HIV protease and HIV infection protection on MT4 cell cultures.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm0208323