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The effect of 17-N substituents on the activity of the opioid κ receptor in nalfurafine derivatives.

Abstract：

:We have previously reported the essential structure of the opioid κ receptor agonist nalfurafine hydrochloride (TRK-820) for binding to the κ receptor. In the course of this study, we focused on the effect of the substituent at 17-N in nalfurafine on the binding affinity for the κ receptor. The exchange of the 17-N substituent in nalfurafine from cyclopropylmethyl to fluoro-substituted alkyl groups, which are strong electron withdrawing substituents, almost completely diminished the binding affinities for the μ and δ opioid receptors, but the binding affinity for the κ receptor was still maintained. As a result, nalfurafine derivatives with 17-fluoro-substituted alkyl groups showed higher selectivities for the κ receptor than did nalfurafine itself. With regard to the κ agonistic activities, the conversion of the 17-N substituent in nalfurafine from cyclopropylmethyl to fluoro-substituted alkyl groups led to the gradual decrease of the agonistic activities in the order corresponding to their binding affinities for the κ receptor. In contrast, the derivative with the bulky 17-isobutyl group showed lower affinity and agonistic activity for the κ receptor than the derivatives with the smaller functional groups. This research suggested that both the electronic property and the steric characteristics of the 17-N substituent would have a great influence on the binding property for the κ receptor.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Nemoto T,Yamamoto N,Wada N,Harada Y,Tomatsu M,Ishihara M,Hirayama S,Iwai T,Fujii H,Nagase H

doi

10.1016/j.bmcl.2012.10.100

subject

Has Abstract

pub_date

2013-01-01 00:00:00

pages

268-72

issue

1

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(12)01402-3

journal_volume

23

pub_type

杂志文章

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