Synthesis and antimicrobial activity of novel 5-amino-4-cyano-1H-pyrazole and quinazolin-4(3H)-one derivatives

Arch Pharm Res. 2010 Dec;33(12):1891-900. doi: 10.1007/s12272-010-1202-5. Epub 2010 Dec 30.

Abstract

New substituted aroylhydrazones (4a-f) were synthesized from the acid hydrazide (3) and the corresponding aldehyde or aldose. 5-Amino-4-cyano-1H-pyrazole derivatives (6a-f) were prepared by the reaction of the aroylhydrazones (4a-f) with malononitrile. The synthesized compounds were tested for antimicrobial activity against various bacteria and fungi and showed moderate to high inhibition activities. Compounds incorporating a sugar moiety as well as a pyrazolyl ring in their structure displayed the highest antimicrobial activity.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Aspergillus / drug effects
  • Candida albicans / drug effects
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Hydrazones / chemical synthesis*
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Quinazolinones / chemical synthesis*
  • Quinazolinones / chemistry
  • Quinazolinones / pharmacology*

Substances

  • 5-amino-4-cyano-1H-pyrazole
  • Anti-Infective Agents
  • Hydrazones
  • Pyrazoles
  • Quinazolinones