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Synthesis of novel 5H-Pyrimido[5,4-b]mdole-(1H,3H)2,4-diones as potential ligands for the cloned α1-adrenoceptor subtypes

✍ Scribed by G. Romeo; F. Russo; A. De Blasi

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
47 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new series of 3‐[ω‐[4‐(4‐substituted phenyl)piperazin‐1‐yl]alkyl]‐5__H__‐pyrimido[5,4‐b]indole‐(1__H__,3__H__)‐2,4‐diones (3–10 and 12–13) were synthesized from the N‐(2‐chloroethyl)‐N'‐[3‐(2‐ethoxycarbonyl)indolyl] urea (1) or the N‐(3‐chloropropyl)‐N'‐[3‐(2‐ethoxycarbonyl)indolyl] urea (2) and a number of 1‐(4‐substi‐tuted‐phenyl)piperazines. 3‐[2‐[4‐(4‐Aminophenyl)piperazin‐1‐yl]ethyl]‐5__H__‐pyrimido[5,4‐b]indole‐(1__H__,3__H__)2,4‐dione (14) was obtained by reduction of the parent nitro compound 8. The obtained 5__H__‐pyrimido[5,4‐b]indole‐(1__H__,3__H__)2,4‐dione derivatives were tested towards cloned α~1A~, α~1B~ and α~1D~ adrenergic receptors subtypes in binding assays. Some compounds showed good affinity and selectivity for the α~1D~‐adrenoceptor subtype.

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