Synthesis of Tetracyclic Pyrido[2,3-b]azepine Derivatives as Analogues of Mirtazapine via N-Acyliminium Ion Cyclization

Tetracyclic pyrido[2,3-b]azepine derivatives 4a-d and 4f as analogues of mirtazapine were synthesized via N-acyliminium ion cyclization by using aromatic rings such as benzene and thiophene ring as a ${\pi}-nucleophile$, and evaluated for the binding affinity for ${\alpha}2-adrenoceptor$. Among test...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2002, Vol.23 (11), p.1623-1628
Main Authors: Lee, Jae-Yeol, Bang, Sung-Hun, Lee, Sook-Ja, Song, Yun-Seon, Jin, Chang-Bae, Park, Ho-Koon, Lee, Yong-Sup
Format: Article
Language:Korean
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Summary:Tetracyclic pyrido[2,3-b]azepine derivatives 4a-d and 4f as analogues of mirtazapine were synthesized via N-acyliminium ion cyclization by using aromatic rings such as benzene and thiophene ring as a ${\pi}-nucleophile$, and evaluated for the binding affinity for ${\alpha}2-adrenoceptor$. Among tested compounds, 2,3,9,13b-tetrahydro-1H-benzo[f]pyrrolo[2,1-a]pyrido[2,3-c]azepine (4a) was the most potent (Ki = 0.26 ${\mu}M)$ but showed about 3-fold less binding affinity than mirtazapine (Ki = 0.08 ${\mu}M)$ for a2-adrenoceptor.
ISSN:0253-2964
1229-5949