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Exploration of ring size in a series of cyclic vicinal diamines with σ₁ receptor affinity.

Abstract：

:Imidazolidine and 1,4-diazepane analogs of N-(2-benzofuranyl)methyl-N'-(4-alkoxybenzyl)piperazines were prepared to explore the effect of ring contraction and expansion on σ receptor affinity and subtype selectivity within a series of cyclic diamines. In vitro receptor binding assays revealed that all cyclic vicinal diamines possessed affinity and selectivity for σ(1) receptors. The imidazolidines possessed nanomolar σ(1) affinities (K(i)=6.45-53.5 nM), and relatively low levels of subtype selectivity (σ(2)/σ(1)=58-237). However, the piperazines and diazepanes achieved picomolar σ(1) interactions, with K(i) ranges of 0.05-10.28 and 0.10-0.194 nM, respectively. Moreover, the piperazines and diazepanes showed excellent discrimination over the σ(2) receptor, with σ(1) selectivities of 143-16140 and 220-11542, respectively.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Moussa IA,Banister SD,Manoli M,Doddareddy MR,Cui J,Mach RH,Kassiou M

doi

10.1016/j.bmcl.2012.07.026

subject

Has Abstract

pub_date

2012-09-01 00:00:00

pages

5493-7

issue

17

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(12)00893-1

journal_volume

22

pub_type

杂志文章

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