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

Pergamon-Elsevier Science
Publication Date
  • Chim/06 Chimica Organica
  • Chim/08 Chimica Farmaceutica


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.

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