Enaminonitrile in heterocyclic synthesis: synthesis and antimicrobial evaluation of some new pyrazole, isoxazole and pyrimidine derivatives incorporating a benzothiazole moiety

Eur J Med Chem. 2009 Dec;44(12):4813-8. doi: 10.1016/j.ejmech.2009.07.024. Epub 2009 Jul 30.

Abstract

Enaminonitrile 2 was used as key intermediate for the synthesis of polyfunctionally substituted heterocycles (e.g. pyrazoles, isoxazole, pyrimidines, thiazolo[3,2-a]pyrimidine, tetrazolo[1,5-a]pyrimidine, pyrido[1,2-a]pyrimidine, 1,5-benzodiazepine, and pyrazolo[1,5-a]pyrimidine) incorporating benzothiazole moiety via its reactions with some N-nucleophiles. The newly synthesized compounds were characterized by IR, (1)H NMR and mass spectral studies. Representative compounds of the synthesized products were tested and evaluated as antimicrobial agents.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Antifungal Agents* / chemical synthesis
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Bacteria / drug effects*
  • Benzothiazoles / chemical synthesis
  • Benzothiazoles / chemistry
  • Botrytis / drug effects*
  • Drug Design
  • Fusarium / drug effects*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / pharmacology
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / pharmacology
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Benzothiazoles
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 2-Ring
  • Isoxazoles
  • Nitriles
  • Pyrazoles
  • Pyrimidines
  • enaminonitrile
  • benzothiazole