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Synthesis and anticonvulsant activity of a class of 2-amino 3-hydroxypropanamide and 2-aminoacetamide derivatives.

Abstract：

:Several studies have demonstrated that N-substituted amino acid derivatives exhibit weak anticonvulsant activities in vivo. In the present study, a series of amides of aminoacids structurally related to aminoacetamide have been synthesised and investigated for anticonvulsant activity. Among the molecules investigated, those containing a bicyclic (tetralinyl, indanyl) group linked to the aminoacetamide chain (40, 47 and 59) were among the most active as anticonvulsants (ED50 > 10, <100 mg/kg after oral administration) against tonic seizures in the mouse maximal electroshock, bicuculline and picrotoxin tests at doses devoid of neurotoxic activity. Altogether, these results suggest the described compounds as a class of orally available anticonvulsants. The ability of these compounds to partially block veratridine-induced aspartate efflux from rat cortical synaptosomes suggests that their anticonvulsant activity may be only partly the consequence of an interaction with neuronal voltage-dependent sodium channels. Some of the most potent compounds appear worthy of a further investigation aimed at assessing their anticonvulsant activity in other models and at elucidating the underlying mechanism of action.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ghidini E,Delcanale M,De Fanti R,Rizzi A,Mazzuferi M,Rodi D,Simonato M,Lipreri M,Bassani F,Battipaglia L,Bergamaschi M,Villetti G

doi

10.1016/j.bmc.2005.12.064

subject

Has Abstract

pub_date

2006-05-15 00:00:00

pages

3263-74

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)01225-3

journal_volume

14

pub_type

杂志文章

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