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

Kiyoi, Takao and York, Mark and Francis, Stuart and Edwards, Darren and Walker, Glenn and Houghton, Andrea K and Cottney, Jean E and Baker, James and Adam, Julia M (2010) Design, synthesis, and structure-activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists. Bioorganic and Medicinal Chemistry Letters, 20 (16). pp. 4918-4921. ISSN 0960-894X

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Abstract

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.