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Synthesis and D2-like binding affinity of new derivatives of N-(1-ethyl-2-pyrrolidinylmethyl)-4,5-dihydro-1H-benzo[g]indole-3-carboxamide and related 4H-[1]benzothiopyrano[4,3-b]pyrrole and 5,6-dihydro-4H-benzo[6,7]cyclohepta[b]pyrrole-3-carboxamide analogues

Pinna, Gérard Aimé and Pirisi, Maria Antonietta and Chelucci, Giorgio Adolfo and Mussinu, Jean-Mario and Murineddu, Gabriele and Loriga, Giovanni and D'Aquila, Paolo Stefano and Serra, Gino (2002) Synthesis and D2-like binding affinity of new derivatives of N-(1-ethyl-2-pyrrolidinylmethyl)-4,5-dihydro-1H-benzo[g]indole-3-carboxamide and related 4H-[1]benzothiopyrano[4,3-b]pyrrole and 5,6-dihydro-4H-benzo[6,7]cyclohepta[b]pyrrole-3-carboxamide analogues. Bioorganic & Medicinal Chemistry, Vol. 10 (8), p. 2485-2496. ISSN 0968-0896. Article.

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DOI: 10.1016/S0968-0896(02)00118-9

Abstract

Various new derivatives and structural analogues of N-(1-ethyl-2-pyrrolidinylmethyl)-4,5-dihydro-1H-benzo[g]indole-3-carboxamide (2a), a representative term of a series of 2-aminomethylpyrrolidinyl derived 4,5-dihydrobenzo[g]indolcarboxamides with good D2-like affinity, were synthesized and evaluated for their ability to bind to dopamine D2-like receptors in vitro. The structural contribution to D2-like receptor binding of the 4,5-dihydrobenzo[g]indole portion of the molecule was examined. From these studies, compound 2k, 2-chloro-N-(1-ethyl-2-pyrrolidinylmethyl)-5,6-dihydro-4H-benzo[6,7]cyclohepta[b]pyrrole-3-carboxamide, was found to possess a potent affinity for D2-like receptors. Behavioural tests in rats have shown that this compound reduces the hyperactivity induced by amphetamine, a property shared by all antipsychotic drugs, at a dose which failed to induce catalepsy, an effect which is predictive of extrapyramidal side effects in humans. The other compounds demonstrated moderate (2c, 2h, and 2j) or no affinity for D2-like receptors.

Item Type:Article
ID Code:385
Status:Published
Refereed:Yes
Uncontrolled Keywords:Benzene derivatives, nitrogen heterocycle, carboxamide, chemical synthesis, biological fixation, D2 receptors
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Area 03 - Scienze chimiche > CHIM/08 Chimica farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Pergamon-Elsevier Science
ISSN:0968-0896
Copyright Holders:© 2002 Elsevier Science
Deposited On:18 Aug 2009 10:02

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