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

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

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Abstract

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 beta-L-1,3- thiazolidine nucleoside analogues. These analogues are all derived from the key stereochemically defined intermediate Ntert- 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, 13C NMR, Mass, elemental analysis and NOE experiments. Docking and antitumor activity of these nucleoside analogues are also reported.

Item Type: Article
Subjects: Pharmacy > MCOPS Manipal > Pharmacology
Depositing User: KMC Manipal
Date Deposited: 23 Jan 2012 06:39
Last Modified: 23 Jan 2012 06:39
URI: http://eprints.manipal.edu/id/eprint/2669

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