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  • Title: Absolute configuration and biological activity of mequitamium iodide enantiomers.
    Author: Di Bugno C, Dapporto P, Giorgi R, Manzini S, Paoli P, Subissi A, Arcamone F.
    Journal: Chirality; 1994; 6(5):382-8. PubMed ID: 8068497.
    Abstract:
    The enantiomers of 1-methyl-3-(10H-phenothiazine-10-ylmethyl)-1-azoniabicyclo[2 ,2,2]octane iodide (1) were prepared by chiral chromatographic resolution of the precursor mequitazine (2). The (+)-(S)-enantiomer 1b is 10-fold more potent than (-)-(R)-enantiomer 1a as a histamine antagonist, while the two enantiomers show the same antimuscarinic activity in vitro. The absolute configuration of the more active dextrorotatory isomer has been determined by X-ray analysis. Conformational analysis and molecular modeling suggest that the (+)-(S)-enantiomer can adopt a conformation similar to that attributed to the receptor binding conformers of classical antihistamines.
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