Stereoisomers of cyclic urea HIV-1 protease inhibitors: synthesis and binding affinities.

Kaltenbach, R F; Nugiel, D A; Lam, P Y; Klabe, R M; Seitz, S P

Kaltenbach, R F; Nugiel, D A; Lam, P Y; Klabe, R M; Seitz, S P.

Afiliación

Kaltenbach RF; DuPont Merck Pharmaceutical Company, P.O. Box 80500, Wilmington, Delaware 19880-0500, USA.

J Med Chem ; 41(25): 5113-7, 1998 Dec 03.

Article en En | MEDLINE | ID: mdl-9836627

RESUMEN

We have synthesized stereoisomers of cyclic urea HIV-1 protease inhibitors to study the effect of varying configurations on binding affinities. Four different synthetic approaches were used to prepare the desired cyclic urea stereoisomers. The original cyclic urea synthesis using amino acid starting materials was used to prepare three isomers. Three additional isomers were prepared by synthetic routes utilizing L-tartaric acid and D-sorbitol as chiral starting materials. A stereoselective hydroxyl inversion of the cyclic urea trans-diol was used to prepare three additional isomers. In all 9 of the 10 possible cyclic urea stereoisomers were prepared, and their binding affinities are described.

Asunto(s)

Fármacos Anti-VIH/síntesis química; Inhibidores de la Proteasa del VIH/síntesis química; Proteasa del VIH/metabolismo; Urea/análogos & derivados; Urea/síntesis química; Fármacos Anti-VIH/química; Fármacos Anti-VIH/metabolismo; Inhibidores de la Proteasa del VIH/química; Inhibidores de la Proteasa del VIH/metabolismo; Unión Proteica; Estereoisomerismo; Relación Estructura-Actividad; Urea/química; Urea/metabolismo

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Urea / Proteasa del VIH / Inhibidores de la Proteasa del VIH / Fármacos Anti-VIH Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 1998 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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