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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| Published in: | Journal of medicinal chemistry Vol. 45; no. 15; pp. 3321 - 3324 |
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| Main Authors: | , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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American Chemical Society
18-07-2002
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | De Michelis, Céline Rocheblave, Luc Bonnet, Brice Bihel, Frédéric Chermann, Jean-Claude Courcambeck, Jérôme Kraus, Jean-Louis Priem, Ghislaine |
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| Cites_doi | 10.1016/0960-894X(96)00035-2 10.1016/S0163-7258(00)00037-1 10.1016/0165-022X(93)90003-7 10.1126/science.3006247 10.1128/CMR.8.2.200 10.1021/ja00351a071 10.1038/329351a0 10.1016/S0166-3542(98)00011-4 10.1073/pnas.90.2.562 10.1038/313284a0 10.1038/313450a0 10.1021/jm9903848 10.2174/1381612802666220921175941 10.1126/science.2420008 10.1016/0092-8674(85)90303-4 10.1016/0042-6822(91)90474-P 10.1021/cr950066q 10.1016/S0040-4039(00)79283-5 |
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| Keywords | Sulfonamide HIV-1 virus Enzyme Benzene derivatives Furan derivatives Retroviridae Enzyme inhibitor Virus replication cycle Oxygen heterocycle Lentivirus In vitro Virus Peptidases Structure activity relation Hydrolases Antiviral Human immunodeficiency virus Inhibition Secondary alcohol Chemical synthesis Diastereomer Aromatic amine |
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| SubjectTerms | Anti-HIV Agents - chemical synthesis Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Carbamates Cell Line Chemical Sciences HIV Protease - metabolism HIV Protease Inhibitors - chemical synthesis HIV Protease Inhibitors - chemistry HIV Protease Inhibitors - pharmacology HIV-1 - drug effects Humans Medical sciences Medicinal Chemistry Pharmacology. Drug treatments Stereoisomerism Structure-Activity Relationship Sulfonamides - chemistry Virus Replication |
| Title | Synthesis and Antiviral Activity of New Anti-HIV Amprenavir Bioisosteres |
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