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Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

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

Author(s): Shimoga Nagaraj Sriharsha, Karkala Sreedhara Ranganath Pai, Suhas, Sheena Shashikanth, Nagasuma Chandra and Kandigere Ramaiah Prabhu

Volume 3, Issue 5, 2007

Page: [425 - 432] Pages: 8

DOI: 10.2174/157340607781745500

Price: $65

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 β-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.

Keywords: β-L-1,3-thiazolidine nucleoside analogues, docking, EAC model, anti-tumor activity


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