A regio- and stereo-controlled approach to triazoloquinoxalinyl C-nucleosides

Carbohydr Res. 2010 Nov 22;345(17):2474-84. doi: 10.1016/j.carres.2010.08.010. Epub 2010 Oct 9.

Abstract

The synthesis of a new series of acyclic triazoloquinoxalinyl C-nucleosides and their transformation to their cyclic analogs are described following protection, activation, and deprotection with subsequent intramolecular nucleophilic substitution protocol. The antibacterial potency of the new compounds was determined using an inhibition zone diameter test. The results show that 3a and 2b exhibit good activity against Escherichiacoli and Candidaalbicans. On the other hand, the cyclic mesylated C-nucleoside 13 showed activity against the Gram-positive bacteria (Staphylococcusaureus) and antifungal activity against C. albicans.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Bacteria / drug effects
  • Carbohydrate Conformation
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Nucleosides / pharmacology
  • Quantum Theory
  • Quinoxalines / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Anti-Infective Agents
  • Nucleosides
  • Quinoxalines