Synthesis and antimycobacterial activity of calpinactam derivatives

Bioorg Med Chem Lett. 2012 Dec 15;22(24):7739-41. doi: 10.1016/j.bmcl.2012.09.069. Epub 2012 Oct 12.

Abstract

Synthesis of calpinactam 1, a fungal antimycobacterial metabolite, utilizing solid-phase peptide synthesis is described. To explore the structure-activity relationships of 1, its derivatives with different amino acids were also synthesized on the basis of the same synthetic strategy. These derivatives were examined for antimycobacterial activity against Mycobacterium smegmatis. Among them, only peptide 6d having d-Ala in place of d-Glu showed moderate activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Caprolactam / analogs & derivatives*
  • Caprolactam / chemical synthesis
  • Caprolactam / chemistry
  • Caprolactam / pharmacology
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium smegmatis / drug effects*
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Oligopeptides
  • calpinactam
  • Caprolactam