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Novel and Selective Partial Agonists of 5-HT3 Receptors. 2. Synthesis and Biological Evaluation of Piperazinopyridopyrrolopyrazines, Piperazinopyrroloquinoxalines, and Piperazinopyridopyrroloquinoxalines

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Centre d'Etudes et de Recherche sur le Médicament de Normandie, Université de Caen, 1, rue Vaubénard, 14032 Caen Cedex, France, ADIR, 1, rue Carle Hébert, 92415 Courbevoie Cedex, France, IRI Servier, 6, place des Pléiades, 92415 Courbevoie Cedex, France, Laboratoire de Psychophysiologie, 7 rue de l'Université, 67000 Strasbourg, France, and INSERM U288, CHU Pitié−Salpétrière, 75634 Paris Cedex 13, France
Cite this: J. Med. Chem. 1997, 40, 12, 1808–1819
Publication Date (Web):June 6, 1997
https://doi.org/10.1021/jm960501o
Copyright © 1997 American Chemical Society
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    Abstract

    In continuation of our previous work on piperazinopyrrolothienopyrazine derivatives, three series of piperazinopyridopyrrolopyrazines, piperazinopyrroloquinoxalines, and piperazinopyridopyrroloquinoxalines were prepared and evaluated as 5-HT3 receptor ligands. The chemical modifications performed within these new series led to structure−activity relationships regarding both high affinity and selectivity for the 5-HT3 receptors that are in agreement with those established previously for the pyrrolothienopyrazine series. The best compound (8a) obtained in these new series is in the picomolar range of affinity for 5-HT3 receptors with a selectivity higher than 106. Four of the high-affinity 5-HT3 ligands (8a, 15a,b, and 16d) were selected in both the pyridopyrrolopyrazine and the pyrroloquinoxaline series and were characterized in vitro and in vivo as agonists or partial agonists. Compound 8a was also evaluated in the light/dark test where it showed potential anxiolytic-like activity at very low doses per os.

    †

     Université de Caen.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    ‡

     ADIR.

    §

     IRI Servier.

    ‖

     Université de Strasbourg.

    ⊥

     INSERM U288.

    ✗

     Abstract published in Advance ACS Abstracts, May 1, 1997.

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