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Issue 12, 2019
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Introducing nitrogen atoms to amidoalkylindoles: potent and selective cannabinoid type 2 receptor agonists with improved aqueous solubility

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Abstract

Previously we identified a series of amidoalkylindoles as potent and selective CB2 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 (EC50,CB1 = NA, EC50,CB2 = 0.067 μM) and azaindole 24 (EC50,CB1 = NA, EC50,CB2 = 0.048 μM) were found to be potent and selective CB2 receptor partial agonists, both with improved aqueous solubility.

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

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Supplementary files

Article information


Submitted
23 Aug 2019
Accepted
25 Oct 2019
First published
18 Nov 2019

Med. Chem. Commun., 2019,10, 2131-2139
Article type
Research Article

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

Y. Ji, Z. Wang, F. Pei, J. Shi, J. Li, H. Gunosewoyo, F. Yang, J. Tang, X. Xie and L. Yu, Med. Chem. Commun., 2019, 10, 2131
DOI: 10.1039/C9MD00411D

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