Novel Nucleoside Analogues: First Synthesis of Pyridine-4-Thioglycosides and Their Cytotoxic Evaluation

Abstract

The reaction of sodium 2,2-dicyanoethene-1,1-bis(thiolate) with 2-cyano-N-arylacetamides afforded sodium pyridine-4-thiolates, coupling of the latters with 2,3,4,6-tetra-O-acetyl-D-gluco- and D-galactopyranosyl bromides, respectively, afforded new pyridine-4-thioglycosides. Ammonolysis of the latter compounds afforded the free thioglycosides. The antitumor activities of the synthesized compounds were tested against human tumor cell lines; lung (A549), colon (HCT116), liver (HEPG2), and prostate (PC3).

Keywords:

• Ketene dithioacetals
• sodium pyridine-4-thiolates
• pyridine-4-thioglycosides
• activated nitriles