title: Stereoselective synthesis of 3,3-diarylacrylonitriles as tubulin polymerization inhibitors.
abstract: A series of 3,3-diarylacrylonitriles were synthesized stereoselectively as tubulin polymerization inhibitors for potential use in cancer chemotherapy. This synthetic route features stannylcupration and palladium-catalyzed Stille cross-coupling chemistry, allowing both E and Z isomers of 3,3-diarylacrylonitriles to be prepared in a very short sequence of reactions.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and Purdue Cancer Center, Purdue University, West Lafayette, IN 47907, USA.
authors.forename: Zhenglai
authors.initials: Z
authors.lastname: Fang
authors.forename: Yunlong
authors.initials: Y
authors.lastname: Song
authors.forename: Taradas
authors.initials: T
authors.lastname: Sarkar
authors.forename: Ernest
authors.initials: E
authors.lastname: Hamel
authors.forename: William E
authors.initials: WE
authors.lastname: Fogler
authors.forename: Gregory E
authors.initials: GE
authors.lastname: Agoston
authors.forename: Phillip E
authors.initials: PE
authors.lastname: Fanwick
authors.forename: Mark
authors.initials: M
authors.lastname: Cushman
mesh_terms: D001704:Biopolymers / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D014404:Tubulin / Q000737:chemistry*
chemical_list: D001704:Biopolymers; D009570:Nitriles; D014404:Tubulin