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A new class of HIV-1 protease inhibitors containing a tertiary alcohol in the transition-state mimicking scaffold
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
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2005 (English)In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 48, no 25, 8098-8102 p.Article in journal (Refereed) Published
Abstract [en]

Novel HIV-1 protease inhibitors encompassing a tertiary alcohol as part of the transition-state mimicking unit have been synthesized. Variation of the P1‘−P3‘ residues and alteration of the tertiary alcohol absolute stereochemistry afforded 10 inhibitors. High potencies for the compounds with (S)-configuration at the carbon carrying the tertiary hydroxyl group were achieved with Ki values down to 2.4 nM. X-ray crystallographic data for a representative compound in complex with HIV-1 protease are presented.

Place, publisher, year, edition, pages
2005. Vol. 48, no 25, 8098-8102 p.
Keyword [en]
Alcohols/*chemistry, Cell Line, Cell Membrane Permeability, Crystallography; X-Ray, Drug Resistance; Viral, HIV Protease/*chemistry/genetics/*metabolism, HIV Protease Inhibitors/*chemical synthesis/chemistry/pharmacology, HIV-1/drug effects/isolation & purification, Humans, Molecular Conformation, Molecular Mimicry, Mutation, Research Support; Non-U.S. Gov't, Stereoisomerism
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-75610DOI: 10.1021/jm050790tPubMedID: 16335934OAI: oai:DiVA.org:uu-75610DiVA: diva2:103521
Available from: 2008-01-29 Created: 2008-01-29 Last updated: 2017-12-14Bibliographically approved

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Hallberg, Anders

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