Synthesis, docking and anti-tumor activity of β-L-1,3-thiazolidine pyrimidine nucleoside analogues

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, 13C NMR, Mass, elemental analysis and NOE experiments. Docking and antitumor activity of these nucleoside analogues are also reported. © 2007 Bentham Science Publishers Ltd.