Issue 12, 2013
From the journal:

Organic & Biomolecular Chemistry

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,‡a   Muralidhar R. Mallireddigari,‡a   Stephen C. Cosenza,b   Balaiah Akula,a   D. R. C. Venkata Subbaiah,b   E. Premkumar Reddyb  and  M. V. Ramana Reddy*b  

* Corresponding authors

a Department of Medicinal Chemistry, Onconova Therapeutics Inc., 375 Pheasant Run, Newtown, PA 18940-3423, USA

b Department of Oncological Sciences, Mount Sinai School of Medicine, Icahn Medical Institute, 1425 Madison Ave., New York, NY 10029-6514, USA
E-mail: r.reddy@mssm.edu
Fax: +1 215 893 6989
Tel: +1 212 659 6875

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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Article information

DOI
https://doi.org/10.1039/C3OB27220F
Article type
Paper
Submitted
14 Nov 2012
Accepted
18 Jan 2013
First published
22 Jan 2013

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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