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Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity

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Filomena Corbo,^† Carlo Franchini,*^† Giovanni Lentini,^† Marilena Muraglia,^† Carla Ghelardini,^‡ Rosanna Matucci,^‡ Nicoletta Galeotti,^‡ Elisa Vivoli,^‡ and Vincenzo Tortorella^†

Department of Pharmaceutical Chemistry, University of Bari, Via E. Orabona n.4, 70125 Bari, Italy, and Department of Preclinical and Clinical Pharmacology, University of Florence, viale G. Pieraccini, 5/6 − 50139, Florence, Italy

J. Med. Chem., 2007, 50 (8), pp 1907–1915

DOI: 10.1021/jm061078e

Publication Date (Web): March 21, 2007

Abstract

Tocainide and related optically active chiral α-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f−i), and the replacement of the CO group with the CS (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a−c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b−e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.

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