title: Regio- and stereoselective syntheses of the natural product CCR5 antagonist anibamine and its three olefin isomers.
abstract: The syntheses of the natural product anibamine and its three olefin isomers have been achieved concisely and efficiently via highly regio- and stereoselective reactions. The crucial steps included a regioselective palladium-catalyzed alkynylation by Sonogashira coupling and a stereoselective Suzuki coupling. Further conformation analyses and in vitro calcium mobilization studies were carried out to characterize the compounds' biological properties.
authors.affiliation: Department of Medicinal Chemistry, Virginia Commonwealth University, 800 East Leigh Street, Richmond, Virginia 23298, United States.
authors.forename: Feng
authors.initials: F
authors.lastname: Zhang
authors.forename: Saheem
authors.initials: S
authors.lastname: Zaidi
authors.forename: Kendra M
authors.initials: KM
authors.lastname: Haney
authors.forename: Glen E
authors.initials: GE
authors.lastname: Kellogg
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D065100:CCR5 Receptor Antagonists; D002460:Cell Line; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D001688:Biological Products; D065100:CCR5 Receptor Antagonists; D011725:Pyridines; C488244:anibamine