Synthesis of new N-analogous corollosporine derivatives with antibacterial activity by laccase-catalyzed amination

Chem Pharm Bull (Tokyo). 2008 Jun;56(6):781-6. doi: 10.1248/cpb.56.781.

Abstract

Corollosporine isolated from the marine fungus Corollospora maritima and N-analogous corollosporines are antimicrobial substances. Owing to the basic structure of the N-analogous corollosporines, they have become an attractive target for laccase-catalyzed derivatisation. In this regard we report on the straightforward laccase-catalyzed amination of dihydroxylated arenes with N-analogous corollosporines. In biological assays the obtained amination products are more active than the parent compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology
  • Bacteria / drug effects
  • Candida / drug effects
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Laccase / metabolism*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Phthalic Anhydrides / chemical synthesis*
  • Phthalic Anhydrides / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Phthalic Anhydrides
  • corollosporine
  • Laccase