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

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, a...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2023-06, Vol.28 (12), p.4734
Hauptverfasser: Chiba, Arisa, Tanaka, Ryoko, Hotta, Mayuno, Nakamura, Kayo, Makino, Kosho, Tabata, Hidetsugu, Oshitari, Tetsuta, Natsugari, Hideaki, Takahashi, Hideyo
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Sprache:eng
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Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28124734