2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents

Palwinder Singh; Anu Mittal; Satwinderjeet Kaur; Wolfgang Holzer; Subodh Kumar

doi:10.1039/B803608J

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2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2inhibitors and cytotoxic agents†

Palwinder Singh,*^a Anu Mittal,^a Satwinderjeet Kaur,^b Wolfgang Holzer^c and Subodh Kumar^a

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* Corresponding authors

^a Department of Chemistry, Guru Nanak Dev University, Amritsar, India
E-mail: palwinder_singh_2000@yahoo.com
Fax: +91-183-2258819
Tel: +91-183-2258802-3495

^b Department of Botanical & Environmental Sciences, Guru Nanak Dev University, Amritsar, India

^c Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse-14, Wein, Austria

Abstract

2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofuran-3-ols were designed and synthesized by the allylations of benzoins followed by iodocyclization and nucleophilic replacement reactions with ethanthiol. These molecules exhibit IC₅₀ for COX-2 at <10 nM concentration and exhibit average GI₅₀ over all the 59 human tumor cell lines at μM concentration.

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Supplementary files

Experimental data for compounds 24–36, Linpinski values of compounds 38–46 and detailed growth inhibitory data for compounds 38, 40 and 41 are given PDF (150K)

Article information

DOI: https://doi.org/10.1039/B803608J
Article type: Paper
Submitted: 03 Mar 2008
Accepted: 16 Apr 2008
First published: 22 May 2008

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Org. Biomol. Chem., 2008,6, 2706-2712

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2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents

P. Singh, A. Mittal, S. Kaur, W. Holzer and S. Kumar, Org. Biomol. Chem., 2008, 6, 2706 DOI: 10.1039/B803608J

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Organic & Biomolecular Chemistry

2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2inhibitors and cytotoxic agents†

Abstract

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2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents

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