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.
Sriharsha
Shimoga Nagaraj
SN
Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysore 570 006, India.
Satish
Sridharamurthy
S
Shashikanth
Sheena
S
Raveesha
Koteshwara Anandarao
KA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D006092:Gram-Negative Facultatively Anaerobic Rods / Q000187:drug effects; D006095:Gram-Positive Cocci / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D011741:Pyrimidine Nucleosides; D053778:Thiazolidines