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Arzneimittelforschung 2008; 58(11): 537-542
DOI: 10.1055/s-0031-1296554
CNS-active Drugs · Hypnotics · Psychotropics · Sedatives
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and Anticonvulsant Activity of 5-Chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o/p-substituted benzal) hydrazone Derivatives

Mehtap Gökçe
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy Gazi University, Ankara, Turkey
,
Ahmet Emin Geciken
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy Gazi University, Ankara, Turkey
,
Engin Yıldırım
2   Department of Pharmacology, Faculty of Medicine, Osmangazi University, Eskişehir, Turkey
,
Ali Ulvi Tosun
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy Gazi University, Ankara, Turkey
› Author Affiliations
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Publication History

Publication Date:
19 December 2011 (online)

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Abstract

It is well known that some hydrazone derivatives of both 2-oxobenzoxazoline and 2-oxobenzothiazoline exhibit potent anticonvulsant activity. In order to investigate the effects of structural modifications on the biological properties, 14 new hydrazones of 5-chloro-2(3H)-benzox-azolinone-3-acetyl hydrazide were synthesized. The chemical structures of the synthesized compounds were established by IR, 1H-NMR spectral analyses and elementary analyses. The anticonvulsant activities of the title compounds were tested by the penthylenetetrazole induced seizure test. 5-Chloro-2(3H)-benz-oxazolinone-3-acetyl-2-(o-methoxy-benzaldehyde)-hydrazone 4d, 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o-methybenzaldehyde)-hydrazone 4g, 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(p-methylbenzaldehyde)-hydrazone 4h, 5-chloro-2(3H)-benzoxazolino-ne-3-acetyl-2-(p-nitrobenzaldehyde)-hydrazone 4m, and 5-chloro-2(3H)-benzox-azolinone-3-acetyl-2-(p-dimethylamino-benzaldehyde)-hydrazone 4n were found more active than phenytoin (CAS 57-41-0) in the tests.

Key words

Anticonvulsant drugs - 5-Chloro-2(3H)-benzoxazo-linones, acetohydrazide, anticonvulsant activity - benzal hydrazones, synthesis
 

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