Synthesis and biological evaluation of 2,3'-diindolylmethanes as agonists of aryl hydrocarbon receptor

Bioorg Med Chem Lett. 2014 Aug 15;24(16):4023-5. doi: 10.1016/j.bmcl.2014.06.009. Epub 2014 Jun 18.

Abstract

Recent studies suggest that arylhydrocarbon receptor (AhR) may be a target for a number of diseases. Natural product malassezin is a AhR agonist with an interesting 2,3'-diindolylmethane skeleton. We have prepared a series of analogues of natural product malassezin using our recently developed method and tested the activity of these analogues against AhR in a cell-based assay. We found that a methyl substituent at 1'-N can significantly increase the activity and the 2-formyl group is not critical for some diindolylmethanes.

Keywords: Agonist; AhR; Diindolylmethane; Indole; Transcription factor.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dose-Response Relationship, Drug
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Molecular Structure
  • Receptors, Aryl Hydrocarbon / agonists*
  • Structure-Activity Relationship

Substances

  • Indoles
  • Receptors, Aryl Hydrocarbon