Synthesis and antimicrobial activity of some S-beta-D-glucosides of 4-mercaptopyrimidine

Nucleosides Nucleotides Nucleic Acids. 2009 Sep;28(9):835-45. doi: 10.1080/15257770903172639.

Abstract

5-Acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylmercapto)pyramidines 3a-c were obtained by the reaction of 5-acetyl-2-aryl-6-methyl-pyrimidine thiol 1a-c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (2) in aq. KOH/acetone. The reaction of 1a-c with peracetylated galactose 5 and peracetylated ribose 8 under MW irradiation gave 5-acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylmercapto)pyrimidine 6a-c and 5-acetyl-2-aryl-6-methyl-4-(2,3,5-tri-O-acetyl-beta-D-ribofuranosylmercapto)pyrimidines 9a-c. The deprotection of 3a-c, 6a-c, and 9a-c in the presence of methanol and TEA/H(2)O yielded the deprotected products 4a-c, 7a-c, and 10a-c. The structures of the compounds were confirmed by using IR, (1)H, (13)C spectra and microanalysis. Selected members of these compounds were screened for antimicrobial activity.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Molecular Structure
  • Pyrimidine Nucleosides / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Anti-Infective Agents
  • Glucosides
  • Pyrimidine Nucleosides
  • Sulfhydryl Compounds