title: Solid-phase synthesis of the alkenyldiarylmethane (ADAM) series of non-nucleoside HIV-1 reverse transcriptase inhibitors.
abstract: The Sonogashira and Stille cross-coupling reactions have been employed in the synthesis of several non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the alkenyldiarylmethane (ADAM) series. The synthesis has been carried out both in solution and on a solid support. In contrast to previous syntheses of NNRTIs in the ADAM series, the present strategy allows the incorporation of differently substituted aromatic rings in a stereochemically defined fashion. The most potent of the new ADAMs inhibited the cytopathic effect of HIV-1RF in CEM-SS cell culture with an EC50 value of 20 nM.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: G
authors.initials: G
authors.lastname: Xu
authors.forename: T L
authors.initials: TL
authors.lastname: Loftus
authors.forename: H
authors.initials: H
authors.lastname: Wargo
authors.forename: J A
authors.initials: JA
authors.lastname: Turpin
authors.forename: R W
authors.initials: RW
authors.lastname: Buckheit
authors.forename: M
authors.initials: M
authors.lastname: Cushman
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002208:Caproates / Q000138:chemical synthesis / Q000494:pharmacology; D002460:Cell Line; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors*; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D019380:Anti-HIV Agents; D002208:Caproates; D018894:Reverse Transcriptase Inhibitors; D054303:HIV Reverse Transcriptase