Synthesis of biscoumarin and dihydropyran derivatives with promising antitumor and antibacterial activities

Bioorg Med Chem Lett. 2015 Dec 1;25(23):5520-3. doi: 10.1016/j.bmcl.2015.10.063. Epub 2015 Oct 23.

Abstract

Two series of biscoumarin (1-3) and dihydropyran (4-12) derivatives were successfully synthesized as new antitumor and antibacterial agents. The molecular structures of four representative compounds 2, 4, 7 and 10 were confirmed by single crystal X-ray diffraction study. The synthesized compounds (1-12) were evaluated for their antitumor activities against human intestinal epithelial adenocarcinoma cell line (HuTu80), mammary adenocarcinoma cell line (4T1) and pancreatic cancer cell line (PANC1) and antibacterial activities against one drug-sensitive Staphylococcus aureus (S. aureus ATCC 29213) strain and three MRSA strains (MRSA XJ 75302, Mu50, USA 300 LAC). The further mechanism study demonstrated that the most potent compound 1 could obviously inhibit the proliferation of cancer cells via the mechanism to induce apoptosis.

Keywords: Antibacterial; Antitumor; Biscoumarin; Dihydropyran.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects*
  • Carboplatin / chemical synthesis
  • Carboplatin / chemistry
  • Carboplatin / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Crystallography, X-Ray
  • Humans
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Pyrans / pharmacology*
  • Staphylococcus aureus / drug effects*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Coumarins
  • Pyrans
  • 3,4-dihydropyran
  • Carboplatin