Introducing nitrogen atoms to amidoalkylindoles: potent and selective cannabinoid type 2 receptor agonists with improved aqueous solubility

在酰胺烷基吲哚中引入氮原子:高效且选择性强的2型大麻素受体激动剂,具有更高的水溶性

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Abstract

Previously we identified a series of amidoalkylindoles as potent and selective CB(2) partial agonists. In the present study, we report our continuous effort to improve the aqueous solubility by introducing N atoms to the amidoalkylindole framework. Synthesis, characterization, and pharmacology evaluations were described. Bioisosteric replacements of the indole nucleus with an indazole, azaindole and benzimidazole were explored. Benzimidazole 43 (EC(50,CB(1)) = NA, EC(50,CB(2)) = 0.067 μM) and azaindole 24 (EC(50,CB(1)) = NA, EC(50,CB(2)) = 0.048 μM) were found to be potent and selective CB(2) receptor partial agonists, both with improved aqueous solubility.

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