Hydrothiolation of benzyl mercaptan to arylacetylene: Application to the synthesis of (E) and (Z)-isomers of on 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent

Venkat R. Pallela, Muralidhar R. Mallireddigari, Stephen C. Cosenza, Balaiah Akula, D. R.C.Venkata Subbaiah, E. Premkumar Reddy, M. V.Ramana Reddy

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16 Scopus citations

Abstract

A stereoselective and efficient method for free radical addition of benzyl thiol to aryl acetylene in the presence of Et3B-hexane has been developed for the synthesis of (Z) and (E)-styryl benzyl sulfides where base catalyzed hydrothiolations have failed. The scope of this reaction was successfully extended for the synthesis of (E)-ON 01910·Na, a phase III clinical stage anti-cancer agent and its inactive geometrical isomer (Z)-ON 01910·Na. It is interesting to note that all the E-isomers synthesized have shown better cytotoxicity profile on cancer cells compared to the Z-isomers.

Original languageEnglish
Pages (from-to)1964-1977
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number12
DOIs
StatePublished - 28 Mar 2013

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