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Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands.

Abstract：

:We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5'-, 6'-, 7'- or 8'-position of the quinoline ring and revealed that many derivatives with 5'- or 8'-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8'-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ida Y,Matsubara A,Nemoto T,Saito M,Hirayama S,Fujii H,Nagase H

doi

10.1016/j.bmc.2012.08.004

subject

Has Abstract

pub_date

2012-10-01 00:00:00

pages

5810-31

issue

19

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(12)00626-8

journal_volume

20

pub_type

杂志文章

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