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

Nucleosides Nucleotides Nucleic Acids. 2015;34(10):659-73. doi: 10.1080/15257770.2015.1071843. Epub 2015 Oct 13.

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; activated nitriles; pyridine-4-thioglycosides; sodium pyridine-4-thiolates.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Drug Design
  • Humans
  • Male
  • Pyridines / chemical synthesis*
  • Pyridines / toxicity
  • Thioglycosides / chemical synthesis*
  • Thioglycosides / toxicity
  • Thionucleosides / chemical synthesis*
  • Thionucleosides / toxicity

Substances

  • Antineoplastic Agents
  • Pyridines
  • Thioglycosides
  • Thionucleosides