Synthesis, docking and anti-tumor activity of beta-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 beta-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 (1)H NMR, (13)C NMR, Mass, elemental analysis and NOE experiments. Docking and antitumor activity of these nucleoside analogues are also reported.
Sriharsha
Shimoga Nagaraj
SN
Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysore, India.
Pai
Karkala Sreedhara Ranganath
KS
Shashikanth
Sheena
S
Chandra
Nagasuma
N
Prabhu
Kandigere Ramaiah
KR
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002853:Chromatography, Liquid; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D053778:Thiazolidines / Q000737:chemistry*
D000970:Antineoplastic Agents; D011741:Pyrimidine Nucleosides; D053778:Thiazolidines