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

  • Published : 2002.11.20
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Abstract

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.

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References

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  1. Synthesis of Tetracyclic Pyrido[2,3-b]azepine Derivatives as Analogues of Mirtazapine via N-Acyliminium Ion Cyclization. vol.34, pp.17, 2002, https://doi.org/10.1002/chin.200317143
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