title: Synthesis and anti-HIV activity of new C2 symmetric derivatives designed as HIV-1 protease inhibitors.
abstract: The synthesis of several new anti-HIV-1 compounds is described. The new compounds contain a C(2) symmetry axis and a dihidroxyethylene moiety based on the D-tartaric acid back bone. The synthesis of these compounds was achieved in 36-69% overall yields from D-tartaric acid. The protocol included: acetylation of hydroxyl groups, followed by diamide formation and deacetylation or reduction with LiAlH(4). The anti-HIV 1 activities of these substances were evaluated in PM-1 cells, using Indinavir as standard (IC(50) = 0.2 microM). Two amino alcohol derivatives showed good inhibitory activity against the virus, with IC(50) = 2.0 and 4 microM.
authors.affiliation: Laboratorio 641, Ilha do Fundao, Instituto de Química, Universidade do Brasil, Cidade Universitária, CT Bloco A, Rio de Janeiro, RJ 21945-970, Brazil.
authors.forename: Emerson P
authors.initials: EP
authors.lastname: Peçanha
authors.forename: Luciana J O
authors.initials: LJ
authors.lastname: Figueiredo
authors.forename: Rodrigo M
authors.initials: RM
authors.lastname: Brindeiro
authors.forename: Amilcar
authors.initials: A
authors.lastname: Tanuri
authors.forename: Alexandre R
authors.initials: AR
authors.lastname: Calazans
authors.forename: O A C
authors.initials: OA
authors.lastname: Antunes
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002244:Carbon; D002460:Cell Line; D016333:HIV Protease / Q000378:metabolism; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans
chemical_list: D019380:Anti-HIV Agents; D017320:HIV Protease Inhibitors; D002244:Carbon; D016333:HIV Protease