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Issue 12, 2013
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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 14 Nov 2012, accepted on 18 Jan 2013 and first published on 22 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB27220F
Org. Biomol. Chem., 2013,11, 1964-1977

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    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

    V. R. Pallela, M. R. Mallireddigari, S. C. Cosenza, B. Akula, D. R. C. V. Subbaiah, E. P. Reddy and M. V. R. Reddy, Org. Biomol. Chem., 2013, 11, 1964
    DOI: 10.1039/C3OB27220F

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