%0 Journal Article
%T Stereochemical properties of quazepam and its affinity for the GABAA receptor.
%A Takano R
%A Tanaka R
%A Nakamura K
%A Tabata H
%A Oshitari T
%A Natsugari H
%A Takahashi H
%J Bioorg Med Chem Lett
%V 110
%N 0
%D 2024 Sep 15
%M 38914347
%F 2.94
%R 10.1016/j.bmcl.2024.129854
%X C9-methylated quazepam 1 was prepared, and its physicochemical properties were investigated. The atropisomers of 1 were isolated as (a1R, a2S) and (a1S, a2R) isomers. Their absolute configurations were determined based on ECD spectra in comparison with those calculated using the time-dependent density functional theory. Preliminary examination of affinity for the GABAA receptor revealed that the (a1R, a2S) isomer of 1 possessed higher activity than its antipode (a1S, a2R) isomer. The active configuration of C9-methylated quazepam 1 is the same as that of 1,4-benzodiazepin-2-ones.