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Synthesis and biological evaluation of chiral alpha-aminoanilides with central antinociceptive activity.

Abstract：

:Tocainide and related optically active chiral alpha-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 C=O group with the C=S (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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Corbo F,Franchini C,Lentini G,Muraglia M,Ghelardini C,Matucci R,Galeotti N,Vivoli E,Tortorella V

doi

10.1021/jm061078e

subject

Has Abstract

pub_date

2007-04-19 00:00:00

pages

1907-15

issue

8

eissn

0022-2623

issn

1520-4804

journal_volume

50

pub_type

杂志文章

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