Stereochemistry of N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones.

Content Provider	Europe PMC
Author	Chiba, Arisa Tanaka, Ryoko Hotta, Mayuno Nakamura, Kayo Makino, Kosho Tabata, Hidetsugu Oshitari, Tetsuta Natsugari, Hideaki Takahashi, Hideyo
Editor	Cera, Gianpiero Qin, Wenling
Copyright Year	2023
Abstract	The stereochemical properties of N-acyl-5H-dibenzo[b,d]azepin-7(6H)-ones (2a-c), which inhibit potassium channels in T cells, were examined by freezing their conformational change due to 4-methyl substitution. N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones exist as pairs of enantiomers [(a1R, a2R), (a1S, a2S)], and each atropisomer is separable at room temperature. An alternate procedure for preparing 5H-dibenzo[b,d]azepin-7(6H)-ones involves the intramolecular Friedel-Crafts cyclization of N-benzyloxycarbonylated biaryl amino acids. Consequently, the N-benzyloxy group was removed during the cyclization reaction to produce 5H-dibenzo[b,d]azepin-7(6H)-ones suitable for the subsequent N-acylation reaction.
Journal	Molecules
Volume Number	28
DOI	10.3390/molecules28124734
PubMed Central reference number	PMC10303827
Issue Number	12
PubMed reference number	37375290
e-ISSN	14203049
Language	English
Publisher	Molecular Diversity Preservation International (MDPI)
Publisher Date	2023-06-13
Access Restriction	Open
Subject Keyword	axial chirality atropisomer dibenzoazepinone Kv1.3
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Medicine Chemistry Drug Discovery Pharmaceutical Science Analytical Chemistry Molecular Medicine Organic Chemistry