Stereoselective Synthesis of 3,3-Diarylacrylonitriles as Tubulin Polymerization Inhibitors

Zhenglai Fang†, Yunlong Song†, Taradas Sarkar‡, Ernest Hamel‡, William E. Fogler§, Gregory E. Agoston§, Phillip E. Fanwick# and Mark Cushman†
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and the Purdue Cancer Center, Purdue University, West Lafayette, Indiana 47907, Toxicology and Pharmacology Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute at Frederick, National Institutes of Health, Frederick, Maryland 21702, EntreMed, Inc., Rockville, Maryland 20850, and Department of Chemistry, Purdue University, West Lafayette, Indiana 47907
J. Org. Chem., 2008, 73 (11), pp 4241–4244
DOI: 10.1021/jo800428b
Publication Date (Web): May 1, 2008
Copyright © 2008 American Chemical Society
†

Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and the Purdue Cancer Center, Purdue University.

,
‡

National Institutes of Health.

,
§

EntreMed, Inc.

,
#

Department of Chemistry, Purdue University.

,
cushman@pharmacy.purdue.edu

Abstract

Abstract Image

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.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Tools

Accession Codes

History

  • Published In Issue June 06, 2008
  • Article ASAPMay 01, 2008
  • Received: February 21, 2008

Recommend & Share

Related Content

Other ACS content by these authors: