Nucleic acid components and their analogs: Design and synthesis of novel cytosine thioglycoside analogs

ABSTRACT

The synthesis of a new category of novel cytosine 4-thioglycoside analogs has been first accomplished. The main step of this strategy is the synthesis of sodium pyrimidine-4-thiolate through the condensation of 2-cyano-N-arylacetamides with sodium cyanocarbonimidodithioate, followed by coupling with α-bromo-sugars to afford the corresponding cytosine 4-thioglycoside analogs. The free thioglycosides were also prepared. Subsequent studies on the application of this strategy for the preparation of other potent pyrimidine thioglycosides are reported.

KEYWORDS:

• Pyrimidine thioglycosides
• antimetabolites
• 2-cyano-N-arylacetamides
• sodium cyanocarbonimidodithioate