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Preparation of Disubstituted Phenyl Propargyl Alcohols, their Use in Oxathiolene Oxide Synthesis, and Evaluation of the Oxathiolene Oxide Products as Anticarcinogenic Enzyme Inducers

[ Vol. 6 , Issue. 3 ]

Author(s):

Maben Ying, Matthew G. Smentek, Rong Ma, Cynthia S. Day, Suzy V. Torti and Mark E. Welker   Pages 242 - 251 ( 10 )

Abstract:


A number of alkynols have been prepared by Sonogoshira coupling of propargyl alcohol to disubstituted aromatic halides. Chelation controlled addition of organometallic nucleophiles to these alkynols was then affected followed by the addition of sulfur dioxide. This methodology was used to prepare a number of oxathiolene oxides which have been screened as NQO1 (quinone oxidoreductase) inducers.

Keywords:

Alkynol synthesis, cancer chemoprevention, sulfur heterocycle synthesis, NQO1

Affiliation:

Department of Chemistry, Wake Forest University, P.O. Box 7486, Winston-Salem, NC 27109, USA.



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