Synthesis and antibacterial activities of cadiolides A, B and C and analogues

Bioorg Med Chem. 2015 Jul 1;23(13):3618-28. doi: 10.1016/j.bmc.2015.04.010. Epub 2015 Apr 10.

Abstract

The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.

Keywords: Antibacterial; Butenolides; Cadiolides; Multicomponent; Natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / pharmacology
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Cell Survival / drug effects
  • Gram-Negative Bacteria / drug effects
  • Gram-Negative Bacteria / growth & development
  • Gram-Positive Bacteria / drug effects
  • Gram-Positive Bacteria / growth & development
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Neutrophils / cytology
  • Neutrophils / drug effects
  • Primary Cell Culture
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • cadiolide A
  • cadiolide B
  • cadiolide C
  • 4-Butyrolactone