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  • Title: 2-Oxopyrrolidines and 6-oxoperhydropyrrolo[1,2-a]pyrazines as templates in the search for nonpeptide cholecystokinin ligands.
    Author: Martín-Martínez M, Ballaz S, Latorre M, Herranz R, García-López MT, Cenarruzabeitia E, Del Río J, González-Muñiz R.
    Journal: Chem Pharm Bull (Tokyo); 1998 May; 46(5):782-6. PubMed ID: 9621412.
    Abstract:
    In order to find new classes of non-peptide cholecystokinin (CCK) ligands, the conformational restriction of a series of weak 3-oxoindolizidine-based CCK antagonists has been both decreased and increased. This tactic yielded a series of monocyclic 2-oxopyrrolidine derivatives 4 with selectivity for CCK-A or CCK-B receptors and with slightly improved binding affinity at the CCK-A receptor subtype with respect to the model 3-oxoindolizidines. In contrast, the incorporation of the Trp residue at the secondary amino group of a pyrrolo[1,2-a]pyrazine template 5, involving a drastic restriction in the conformational flexibility of the molecule, resulted in a series of bicyclic derivatives that did not bind to CCK receptors at concentrations up to 10(-5) M.
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