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

2010; Elsevier BV; Volume: 20; Issue: 16 Linguagem: Inglês

10.1016/j.bmcl.2010.06.067

1464-3405

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

Forensic Toxicology and Drug Analysis

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.