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Synthesis and structure-activity relationship of 5-pyridazin-3-one phenoxypiperidines as potent, selective histamine H-3 receptor inverse agonists
Journal article   Open access   Peer reviewed

Synthesis and structure-activity relationship of 5-pyridazin-3-one phenoxypiperidines as potent, selective histamine H-3 receptor inverse agonists

Ming Tao, Lisa D. Aimone, John A. Gruner, Joanne R. Mathiasen, Zeqi Huang, Jacquelyn Lyons, Rita Raddatz and Robert L. Hudkins
Bioorganic & medicinal chemistry letters, v 22(2), pp 1073-1077
15 Jan 2012
PMID: 22197136
url
https://doi.org/10.7270/q2k64jhtView
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Abstract

Chemistry Chemistry, Medicinal Chemistry, Organic Life Sciences & Biomedicine Pharmacology & Pharmacy Physical Sciences Science & Technology
Optimization of the R-2 and R-6 positions of (5-{4-[3-(R)-2-methylpyrrolin-1-yl-propoxylphenyl)-2H-pyridazin-3-one) 2a with constrained phenoxypiperidines led to the identification of 5-[4-(cyclobutyl-piperidin-4-yloxy)-phenyl]-6-methyl-2H-pyridazin-3-one 8b as a potent, selective histamine H-3 receptor antagonist with favorable pharmacokinetic properties. Compound 8b had an excellent safety genotoxocity profile for a CNS-active compound in the Ames and micronucleus tests, also displayed potent H3R antagonist activity in the brain in the rat dipsogenia model and robust wake activity in the rat EEG/EMG model. (C) 2011 Elsevier Ltd. All rights reserved.

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Web of Science research areas
Chemistry, Medicinal
Chemistry, Organic
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