Microwave-assisted synthesis of dinucleoside analogues containing a thiazolidin-4-one linkage via one-pot tandem Staudinger/aza-Wittig/cyclization

Org Biomol Chem. 2011 Aug 21;9(16):5766-72. doi: 10.1039/c1ob05675a. Epub 2011 Jun 29.

Abstract

Dinucleosides containing a thiazolidin-4-one linkage were prepared by one-pot tandem Staudinger/aza-Wittig/intermolecular cyclization under microwave irradiation and their structures were confirmed. Preliminary examination of HIV-RT inhibition showed that the dinucleosides containing (R)-thiazolidin-4-one linkage are significantly more active than those containing (S)-thiazolidin-4-one linkage.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • HIV Infections / drug therapy
  • HIV Reverse Transcriptase / antagonists & inhibitors*
  • HIV Reverse Transcriptase / metabolism
  • HIV-1 / enzymology*
  • Microwaves
  • Models, Molecular
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Nucleosides / pharmacology
  • Thiazolidines / chemical synthesis
  • Thiazolidines / chemistry*
  • Thiazolidines / pharmacology

Substances

  • Enzyme Inhibitors
  • Nucleosides
  • Thiazolidines
  • HIV Reverse Transcriptase