Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities

Bioorg Chem. 2014 Feb:52:77-82. doi: 10.1016/j.bioorg.2013.11.008. Epub 2013 Dec 7.

Abstract

Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)2/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50=0.52-1.11 μM) compared with BHT (IC50=9.67 μM). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 μg/mL. Structures of newly synthesized compounds were confirmed by IR, (1)H NMR, (13)C NMR data and high-resolution mass spectrometry.

Keywords: 3,4-Dihydromollugin; Antibacterial activity; Antioxidant activity; Mollugin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Drug Evaluation, Preclinical
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrans / chemistry*
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Pyrans
  • rubimaillin