Design, synthesis and antibacterial activity of novel 1,3-thiazolidine pyrimidine nucleoside analogues

The synthesis of a new class of 1,3-thiazolidine nucleoside analogues in which furanose oxygen atom was replaced with nitrogen atom and 2′-carbon atom with sulfur atom is described. N-tert-butoxycarbonyl-2-acyloxy-4-trityloxymethyl-1,3-thiazolidine was coupled with the pyrimidine bases like uracil, thymine, etc. in the presence of lewis acids stannic chloride or trimethyl silyl triflate following Vorbruggen procedure. The antibacterial activity of the novel 1,3-thiazolidine pyrimidine nucleoside analogues is highlighted. All compounds (7a–e) with free NH group in the pyrimidine moiety showed significant biological activity against all the standard strains used and in that compounds 7d and 7e showed significant activity against 14 human pathogens tested.

The new class of 1-(4-hydroxymethyl-1,3-thiazolidine-2-yl) pyrimidine nucleoside analogues were synthesized following Vorbruggen procedure. The characterization of the compounds was accomplished by IR, NMR, mass, elemental analysis and NOE experiments. The antibacterial activity of these compounds against 14 human pathogens is highlighted.Figure optionsDownload as PowerPoint slide