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Design and synthesis of quinolinopropellane derivatives with selective δ opioid receptor agonism.

Abstract：

:Indolopropellane 2 was reported to show almost no binding affinity to the δ opioid receptor (DOR) in spite of the fact that 2 has both the propellane fundamental skeleton (message part) with binding ability to the opioid receptors and a possible DOR address structure (indole moiety). We developed the working hypothesis that almost no binding affinity of 2 to the DOR would be derived from its possibly stable bent conformer. To enable the propellane skeleton to adopt an extended conformation which would reasonably interact with the DOR, quinolinopropellanes 3a-d were designed which had an additional pharmacophore, quinoline nitrogen. The calculated binding free energies of ligand-DOR complexes strongly supported our working hypothesis. The synthesized quinolinopropellane 3a was a selective DOR full agonist, confirming our working hypothesis and the results of in silico investigation.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Nagase H,Nakajima R,Yamamoto N,Hirayama S,Iwai T,Nemoto T,Gouda H,Hirono S,Fujii H

doi

10.1016/j.bmcl.2014.04.098

subject

Has Abstract

pub_date

2014-07-01 00:00:00

pages

2851-4

issue

13

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(14)00455-7

journal_volume

24

pub_type

杂志文章

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