Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities

J Nat Prod. 2005 Nov;68(11):1581-7. doi: 10.1021/np050250z.

Abstract

Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities.

MeSH terms

  • Alkaloids / chemistry*
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Aspergillus fumigatus / drug effects
  • Candida albicans / drug effects
  • Carbolines
  • Cryptococcus neoformans / drug effects
  • Drug Evaluation, Preclinical
  • Indole Alkaloids
  • Indoles* / chemical synthesis
  • Indoles* / chemistry
  • Indoles* / isolation & purification
  • Indoles* / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Naphthyridines* / chemical synthesis
  • Naphthyridines* / chemistry
  • Naphthyridines* / isolation & purification
  • Naphthyridines* / pharmacology
  • Plants, Medicinal / chemistry*
  • Saccharomyces cerevisiae / drug effects
  • Structure-Activity Relationship
  • Trichophyton / drug effects
  • Zanthoxylum / chemistry*

Substances

  • Alkaloids
  • Antifungal Agents
  • Carbolines
  • Indole Alkaloids
  • Indoles
  • Naphthyridines
  • canthin-6-one