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Issue 1, 2017

Synthesis and pharmacological evaluation of novel selective MOR agonist 6β-pyridinyl amidomorphines exhibiting long-lasting antinociception

Author affiliations

Abstract

It was previously reported that 6β-aminomorphinan derivatives show high affinity for opiate receptors. Novel 6β-heteroarylamidomorphinanes were designed based on the MOR selective antagonist NAP. The 6β-aminomorphinanes were prepared by stereoselective Mitsunobu reaction and subsequently acylated with nicotinic acid and isonicotinic acid chloride hydrochlorides. The receptor binding and efficacy were determined in vitro and the analgesic activity was studied in vivo. The in vitro studies revealed moderate selectivity for the MOR. At least two compounds in this series exhibited a long-lasting analgesic response when administered subcutaneously and intracerebroventricularly. When the substances were given intracerebroventricularly to mice, they showed analgesic potency comparable to morphine.

Graphical abstract: Synthesis and pharmacological evaluation of novel selective MOR agonist 6β-pyridinyl amidomorphines exhibiting long-lasting antinociception

Supplementary files

Article information


Submitted
03 Aug 2016
Accepted
04 Oct 2016
First published
18 Oct 2016

This article is Open Access

Med. Chem. Commun., 2017,8, 152-157
Article type
Research Article

Synthesis and pharmacological evaluation of novel selective MOR agonist 6β-pyridinyl amidomorphines exhibiting long-lasting antinociception

Á. Urai, A. Váradi, L. Szőcs, B. Komjáti, V. Le Rouzic, A. Hunkele, G. W. Pasternak, S. Majumdar and S. Hosztafi, Med. Chem. Commun., 2017, 8, 152 DOI: 10.1039/C6MD00450D

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