Cytotoxic and Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives

Chem Biodivers. 2017 Aug;14(8). doi: 10.1002/cbdv.201700077. Epub 2017 Jul 1.

Abstract

A small series of 1-acetyl-2-(4-alkoxy-3-methoxyphenyl)cyclopropanes was prepared, starting from dehydrozingerone (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one) and its O-alkyl derivatives. Their microbiological activities toward some strains of bacteria and fungi were tested, as well as their in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174 and A549). All synthesized compounds showed significant antimicrobial activity and expressed cytotoxic activity against tested carcinoma cell lines, but they showed no significant influence on normal cell line (MRC5). Butyl derivative is the most active on HeLa cells (IC50 = 8.63 μm), while benzyl one is active against LS174 and A549 cell lines (IC50 = 10.17 and 12.15 μm, respectively).

Keywords: Antimicrobial activities; Crystal structure elucidation; Cyclopropyl moiety; Cytotoxic activities; Dehydrozingerone.

MeSH terms

  • A549 Cells
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Cyclopropanes / chemistry
  • Drug Screening Assays, Antitumor
  • Fungi / drug effects
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Structure-Activity Relationship
  • Styrenes / chemistry*
  • Styrenes / toxicity

Substances

  • Anti-Infective Agents
  • Cyclopropanes
  • Styrenes
  • cyclopropene
  • methyl-3-methoxy-4-hydroxystyryl ketone