Synthesis of Biscoumarin and Dihydropyran Derivatives and Evaluation of Their Antibacterial Activity

Molecules. 2015 Sep 18;20(9):17469-82. doi: 10.3390/molecules200917469.

Abstract

In an attempt to find a new class antibacterial agents, a series of biscoumarins (1-4) and dihydropyrans (5-13) were successfully prepared. The molecular structures of four representative compounds, that is, 4, 5, 8 and 12 were confirmed by single crystal X-ray diffraction study. These synthesized compounds were screened for their antibacterial activity in vitro against Staphylococcus aureus (S. aureus ATCC 29213), methicillin-resistant S. aureus (MRSA XJ 75302), vancomycin-intermediate S. aureus (Mu50 ATCC 700699), USA 300 (Los Angeles County clone, LAC), Staphylococcus epidermidis (S. epidermidis ATCC 14990), methicillin-resistant S. epidermidis (MRSE XJ 75284) and Escherichia coli (E. coli ATCC 25922). Additionally, there are two classical intramolecular O-H···O hydrogen bonds (HBs) in biscoumarins 1-4 and the corresponding HB energies were further performed with the density functional theory (DFT) [B3LYP/6-31G*] method.

Keywords: S. aureus; S. epidermidis; biscoumarins; dihydropyran.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Coumarins / chemical synthesis
  • Coumarins / pharmacology*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Molecular Structure
  • Pyrans / chemical synthesis
  • Pyrans / pharmacology*
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects

Substances

  • Anti-Bacterial Agents
  • Coumarins
  • Pyrans