Flustramine inspired synthesis and biological evaluation of pyrroloindoline triazole amides as novel inhibitors of bacterial biofilms

Org Biomol Chem. 2011 Aug 7;9(15):5476-81. doi: 10.1039/c1ob05605k. Epub 2011 Jun 15.

Abstract

Anti-biofilm agents have been developed based upon the flustramine family of alkaloids isolated from Flustra foliacea. A Garg interrupted Fischer indolization reaction was employed to access a core pyrroloindoline scaffold that was subsequently employed to create a pyrroloindoline triazole amide library. Screening for the ability to modulate biofilm formation against strains of Gram-positive and Gram-negative bacteria identified several compounds with low micromolar, non-toxic IC(50) values.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bacteria / drug effects*
  • Biofilms / drug effects*
  • Indole Alkaloids / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology
  • Inhibitory Concentration 50
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Quantitative Structure-Activity Relationship
  • Small Molecule Libraries / chemical synthesis
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology

Substances

  • Amides
  • Anti-Bacterial Agents
  • Indole Alkaloids
  • Indoles
  • Pyrroles
  • Small Molecule Libraries
  • flustramine C
  • indoline