Synthesis and antimicrobial evaluation of novel pyrazolones and pyrazolone nucleosides

Nucleosides Nucleotides Nucleic Acids. 2012;31(11):783-800. doi: 10.1080/15257770.2012.732250.

Abstract

The synthesis of a novel series of 4-arylhydrazono-5-methyl-1,2-dihydropyrazol-3-ones 4a-h, and their N (2)-alkyl and acyclo, glucopyranosyl, and ribofuranosyl derivatives is described. K(2)CO(3) catalyzed alkylation of 4a-h with allyl bromide, propargyl bromide, 4-bromobutyl acetate, 2-acetoxyethoxymethyl bromide, and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide proceeded selectively at the N (2)-position of the pyrazolinone ring. Glycosylation of 4a with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose under Vorbruggen glycosylation conditions gave the corresponding N (2)-4-arylhydrazonopyrazolone ribofuranoside 9a in good yield. Conventional deprotection of the acetyl protected nucleosides furnished the corresponding 4-arylhydrazonopyrazolone nucleosides in good yields. Selected numbers of the newly synthesized compounds were screened for antimicrobial activity. Compounds 4b, 12a, and 14 d showed moderate activities against Aspergillus flavus, Penicillium sp., and Escherichia coli.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Aspergillus flavus / drug effects*
  • Escherichia coli / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry
  • Nucleosides / pharmacology*
  • Penicillium / drug effects*
  • Pyrazolones / chemical synthesis
  • Pyrazolones / chemistry
  • Pyrazolones / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Nucleosides
  • Pyrazolones