New Adamantyl Chalcones: Synthesis, Antimicrobial and Anticancer Activities

Curr Top Med Chem. 2017;17(4):498-506. doi: 10.2174/1568026616666160824121935.

Abstract

Background: A new variety of adamantyl chalcones (2, 3a-o) were efficiently prepared by Claisen-Schmidt reaction of 4-adamantyl acetophenone 2 with a serie of aromatic aldehydes in good yields. Their structures were confirmed by spectroscopic data, and the relative configuration of 3d was confirmed by X-ray crystallography. All synthesized chalcones were tested against a panel of Grampositive and Gram-negative bacteria and pathogenic fungus and displayed strong antibacterial activity against Enterococcus faecali 29212, Pseudomonas aeruginosa ATCC27853, Escherichia coli and interesting antifungal activity against Candida glabrata ATCC 90030.

Result: The effect of these compounds was also tested in vitro as antitumor on Miapaca2 cells. Compounds also showed anticancer activity against human pancreas cancer cell MiaPaca2.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chalcones / chemical synthesis*
  • Chalcones / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Chalcones