Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids

Bioorg Med Chem Lett. 2016 Feb 1;26(3):809-813. doi: 10.1016/j.bmcl.2015.12.089. Epub 2015 Dec 28.

Abstract

The purpose of this study was to synthesize hydrophilic cinnamaldehyde Schiff base compounds and investigate those bioactivity. A total of 24 Schiff base compounds were synthesized using a simple approach with 3 cinnamaldehyde derivates and 8 amino acids as raw materials. The structures of synthesized compounds were confirmed using FTIR, (1)HNMR, HRMS purity and melting point. The antimicrobial activities of new compounds were evaluated with fluconazole and ciprofloxacin as the control against Aspergillus niger, Penicillium citrinum, Escherichia coli and Staphylococcus aureus. Findings show that major compounds exhibited significant bioactivity. Results from the structure-activity relationship suggest that both -p-Cl on benzene ring of cinnamaldehyde and the number of -COOK of amino acid salts significantly contributed to antimicrobial activity.

Keywords: Amino acids; Antibacterial activity; Antimold activity; Cinnamaldehyde; Schiff base.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrolein / analogs & derivatives*
  • Acrolein / chemistry
  • Amino Acids / chemistry*
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Aspergillus niger / drug effects
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Penicillium / drug effects
  • Schiff Bases / chemical synthesis
  • Schiff Bases / chemistry*
  • Schiff Bases / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Anti-Infective Agents
  • Schiff Bases
  • Acrolein
  • cinnamaldehyde