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Axial chirality and affinity at the GABA(A) receptor of pyrimido[1,2-a][1,4]benzodiazepines and related compounds.

Abstract：

:The pyrimido[1,2-a][1,4]benzodiazepines (1a-c) and the 8-membered analogues (diazocines 2a and 2b) were separated into their atropisomers with HPLC on a chiral column. High stereochemical stability was observed in the atropisomer of the 8-membered derivatives (2a and 2b), and the 1,4-benzodiazepine (1c) with 2'-chloro at the pendant phenyl showed a lower energy barrier for the conversion between the atropisomers compared with that with the unsubstituted pendant phenyl (1a). The aR isomer of 1a-c was revealed to be the eutomer in GABA(A) receptor binding, and the eutomer 1c-R showed extremely potent activity with an IC(50) value of 1.5 nM.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Lee S,Kamide T,Tabata H,Takahashi H,Shiro M,Natsugari H

doi

10.1016/j.bmc.2008.09.037

subject

Has Abstract

pub_date

2008-11-01 00:00:00

pages

9519-23

issue

21

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00875-4

journal_volume

16

pub_type

杂志文章

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