Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones

Bioorg Med Chem Lett. 2016 Jan 15;26(2):580-583. doi: 10.1016/j.bmcl.2015.11.070. Epub 2015 Nov 24.

Abstract

An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (μg·mL(-)(1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (μg·mL(-)(1)) against Staphylococcus aureus.

Keywords: 3-N-alkylation; 3-N-benzylation; Antibacterial; Canthin-6-one; Staphylococcus aureus; Structure–activity relationship; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Carbolines / chemical synthesis
  • Carbolines / chemistry*
  • Carbolines / pharmacology*
  • Humans
  • Indole Alkaloids / chemical synthesis
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / pharmacology*
  • Microbial Sensitivity Tests
  • Staphylococcal Infections / drug therapy
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Carbolines
  • Indole Alkaloids
  • canthin-6-one