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ID: ALA1145755

Journal: Bioorg Med Chem Lett

Title: Design, synthesis and biological activity of novel dimethyl-[2-[6-substituted-indol-1-yl]-ethyl]-amine as potent, selective, and orally-bioavailable 5-HT(1D) agonists.

Authors: Isaac M, Slassi M, Xin T, Arora J, O'Brien A, Edwards L, MacLean N, Wilson J, Demschyshyn L, Labrie P, Naismith A, Maddaford S, Papac D, Harrison S, Wang H, Draper S, Tehim A.

Abstract: A novel series of highly potent human 5-HT(1D) agonists, dimethyl-[2-[6-substituted-indol-1-yl]-ethyl]-amine, was synthesized. Structure-activity relationship (SAR) investigation revealed 4-[1-(2-dimethylamino-ethyl)-1H-indol-6-yl]-tetrahydro-thiopyran-4-ol, 11b (ALX-2732), as a potent (K(i)=2.4 nM) agonist at the human 5-HT(1D) receptor with good selectivity over the other serotonin receptor subtypes. This compound demonstrated favorable in vitro metabolic stability in human and rat liver microsomes and was found to be orally bioavailable in rats (F(po)=51%).

CiteXplore: 14643336

DOI: 10.1016/j.bmcl.2003.09.025