Stereoselective synthesis of 3,3-diarylacrylonitriles as tubulin polymerization inhibitors.
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.
Fang
Zhenglai
Z
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and Purdue Cancer Center, Purdue University, West Lafayette, IN 47907, USA.
Song
Yunlong
Y
Sarkar
Taradas
T
Hamel
Ernest
E
Fogler
William E
WE
Agoston
Gregory E
GE
Fanwick
Phillip E
PE
Cushman
Mark
M
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*
D001704:Biopolymers; D009570:Nitriles; D014404:Tubulin