Synthesis of Novel 2- And 6-Alkyl/Arylthiopurine Derivatives

GRAPHICAL ABSTRACT

Abstract

Synthetic methodologies toward different types of novel 2- and 6-alkyl/arylthiopurine nucleosides, including those containing 1,2,3-triazolyl moieties, are described. The title compounds were obtained by S_NAr reactions between 2,6-diazido-, 2,6-dichloro- and 2,6-bis-triazolylpurine nucleosides and different S-nucleophiles. The chemical reactivity of the aforementioned variously substituted purine nucleosides toward different S-nucleophiles is discussed. The obtained monoazido purine nucleoside intermediates exist in azide and tetrazole tautomeric forms. These compounds were later used in 1,3-dipolar cycloaddition reactions with different terminal alkynes. The obtained sulfur-containing nucleoside analogs are interesting in terms of medicinal chemistry.

Keywords:

• Purine nucleosides
• alkyl/arylthiopurine derivatives
• 2,6-diazidopurine nucleoside
• 2,6-dichloropurine nucleoside