Design, synthesis, and structure-activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists

Takao Kiyoi, Mark York, Stuart Francis, Darren Edwards, Glenn Walker, Andrea K Houghton, Jean E Cottney, James Baker, Julia M Adam

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


Novel tricyclic indole-3-carboxamides were synthesized as structurally restricted analogs of bicyclic indoles, and found to be potent CB1 cannabinoid receptor agonists. The CB1 agonist activity depended on the absolute configuration of the chiral center of the tricyclic ring. The preferred enantiomer was more potent than the structurally unconstrained lead compound. Structure-activity relationships in the amide side chain of the indole C-3 position were also investigated.

Original languageEnglish
Pages (from-to)4918-4921
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number16
Publication statusPublished - 15 Aug 2010


  • amides
  • animals
  • drug design
  • humans
  • indoles
  • mice
  • microsomes
  • receptor, Cannabinoid, CB1
  • structure-activity relationships

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