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Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents
(2010)
The 3-deoxy-3-fluoro-6-S-(2-S-pyridyl)-6-thio-beta-D-glucopyranosyl nucleoside analogs 7 were prepared via two facile synthetic routes. Their precursors, 3-fluoro-6-thio-glucopyranosyl nucleosides 5a-e, were obtained by ...
Efficient synthesis of exomethylene- and keto-exomethylene-D-glucopyranosyl nucleoside analogs as potential cytotoxic agents
(2011)
A novel series of exomethylene- and keto-exomethylene-D-glucopyranonucleosides with thymine, uracil, and 5-fluorouracil as heterocyclic bases have been designed and synthesized. Wittig condensation of the 3-keto glucoside ...
A concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivatives
(2008)
The chemical synthesis of 1,2,4-tri-O-acetyl-3-deoxy-3-fluoro-5-thio-D-xylopyranose, 1,2,4,6-tetra-O-acetyl-3-deoxy-3 -fluoro-5-thio-alpha(-D-glucopyranose and their corresponding nucleosides of thymine is described. ...
Keto-fluorothiopyranosyl nucleosides: a convenient synthesis of 2-and 4-keto-3-fluoro-5-thioxylopyranosyl thymine analogs
(2011)
A novel series of fluorinated keto-beta-D-5-thioxylopyranonucleosides bearing thymine as the heterocyclic base have been designed and synthesized. Deprotection of 3-deoxy-3-fluoro-5-S-acetyl-5-thio-D-xylofuranose (1) and ...
Kinetic and in silico analysis of the slow-binding inhibition of human poly(A)-specific ribonuclease (PARN) by novel nucleoside analogues
(2012)
Poly(A)-specific ribonuclease (PARN) is a 3'-exoribonuclease that efficiently degrades poly(A) tails and regulates, in part, mRNA turnover rates. We have previously reported that adenosine- and cytosine-based glucopyranosyl ...
STEREOCONTROLLED FACILE SYNTHESIS AND BIOLOGICAL EVALUATION OF (3 ' S) AND (3 ' R)-3 '-AMINO (AND AZIDO)-3 '-DEOXY PYRANONUCLEOSIDES
(2012)
This article describes the synthesis of (3'S) and (3'R)-3'-amino-3'-deoxy pyranonucleosides and their precursors (3'S) and (3'R)-3'-azido-3'-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesu ...
Branched-chain sugar nucleosides: stereocontrolled synthesis and bioevaluation of novel 3 '-C-trifluoromethyl and 3 '-C-methyl pyranonucleosides
(2015)
A new series of 3 '-C-trifluoromethyl- and 3 '-C-methyl-beta-D-allopyranonucleosides of 5-fluorouracil and their deoxy derivatives has been designed and synthesized. Treatment of ketosugar 1 with trifluoromethyltrimethylsilane ...
Stereocontrolled synthesis of 4 '-C-cyano and 4 '-C-cyano-4 '-deoxy pyrimidine pyranonucleosides as potential chemotherapeutic agents
(2012)
A new series of 4'-C-cyano and 4'-C-cyano-4'-deoxy pyrimidine pyranonucleosides has been designed and synthesized. Commercially available 1,2,3,4,6-penta-O-acetyl-D-mannopyranose (1) was condensed with silylated 5-fluorouracil, ...
Synthesis of 4,6-dideoxy-3-fluoro-2-keto-beta-D-glucopyranosyl analogues of 5-fluorouracil, N-6-benzoyl adenine, uracil, thymine, N-4-benzoyl cytosine and evaluation of their antitumor activities
(2010)
The synthesis of the unsaturated 4,6-dideoxy-3-fluoro-2-keto-beta-D-glucopyranosyl nucleosides of 5-fluorouracil (6a), N-6-benzoyl adenine (6b), uracil (6c), thymine (6d) and N-4-benzoyl cytosine (6e), is described. ...
Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity
(2015)
We report the synthesis of novel thiopurine pyranonucleosides. Direct coupling of silylated 6-mercaptopurine and 6-thioguanine with the appropriate pyranoses 1a-e via Vorbruggen nucleosidation, gave the N-9 linked ...