Synthesis of new pyrazolone and pyrazole-based adamantyl chalcones and antimicrobial activity

Biosci Rep. 2020 Sep 30;40(9):BSR20201950. doi: 10.1042/BSR20201950.

Abstract

Chalcones and their derivatives are becoming increasingly popular due to their various pharmacological effects. Chalcone molecules may be extracted from natural resources, entirely synthesised, or biosynthesised by modifying the natural ones. In the present study, five pyrazole-based adamantyl heterocyclic compounds were synthesised by condensation of 1-adamantyl chalcone with substituted phenylhydrazine. The products were characterised by using ¹H NMR, ¹³C NMR and FT-IR spectroscopy. The microbiological activity of these compounds was investigated against bacteria and fungi. The new compounds showed good to moderate activity against the microbial species used for screening. All developed molecules showed antibacterial activity against Gram-negative and Gram-positive. These molecules showed antifungal activities against Fusarium oxysporum fungus and in a dose-dependent manner, apart from RS-1 molecules which showed compromised antifungal activity and even at a high dose.

Keywords: Adamantyl Chalcones; Chalcone; Pyrazole; Pyrazolone; antibacterial activity.

MeSH terms

  • Adamantane / analogs & derivatives
  • Adamantane / chemical synthesis
  • Adamantane / pharmacology*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Chalcones / chemical synthesis
  • Chalcones / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrazoles / chemistry
  • Pyrazolones / chemistry
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Chalcones
  • Pyrazoles
  • Pyrazolones
  • Adamantane