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Synthesis, Docking and Anti-Tumor Activity of \beta-L-1,3-Thiazolidine Pyrimidine Nucleoside Analogues

Sriharsha, Shimoga Nagaraj and Pai, Karkala Sreedhara Ranganath and Shashikanth, Sheena and Chandra, Nagasuma and Prabhu, Kandigere Ramaiah (2007) Synthesis, Docking and Anti-Tumor Activity of \beta-L-1,3-Thiazolidine Pyrimidine Nucleoside Analogues. In: Medicinal Chemistry, 3 (5). pp. 425-432.

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In the search for effective, selective, and nontoxic antiviral and antitumor agents, a variety of strategies have been devised to design nucleoside analogues. Here we have described the versatile synthesis of β-L-1,3-thiazolidine nucleoside analogues. These analogues are all derived from the key stereochemically defined intermediate N-tert-butoxy-carbonyl-4-hydroxymethyl-1,3-thiazolidine-2-ol which was accessible in 57% yield starting from L-Cysteine methylester hydrochloride. N-tert-butoxycarbonyl-2-acyloxy-4-trityloxymethyl-1,3-thiazolidine was coupled with the pyrimidine bases in the presence of Lewis acids stannic chloride or trimethyl silyl triflate following Vorbruggen procedure. Proof of the structure and configuration was obtained through $^1H$ NMR, $^{13}C$ NMR, Mass, elemental analysis and NOE experiments. Docking and antitumor activity of these nucleoside analogues are also reported.

Item Type: Journal Article
Publication: Medicinal Chemistry
Publisher: Bentham Science Publishers Ltd
Additional Information: Copyright of this article belongs to Bentham Science Publishers Ltd.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 01 Aug 2008
Last Modified: 27 Aug 2008 13:40
URI: http://eprints.iisc.ac.in/id/eprint/15409

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