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

Gokce M., Geciken A. E., YILDIRIM E., Tosun A. U.

ARZNEIMITTELFORSCHUNG-DRUG RESEARCH, vol.58, no.11, pp.537-542, 2008 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 11
  • Publication Date: 2008
  • Doi Number: 10.1055/s-0031-1296554
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.537-542
  • Keywords: Anticonvulsant drugs, 5-Chloro-2(3H)-benzoxazolinones, acetohydrazide, anticonvulsant activity, benzal hydrazones, synthesis, ANTIINFLAMMATORY ACTIVITY, ANTINOCICEPTIVE ACTIVITY, MANNICH-BASES, 2(3H)-BENZOXAZOLONE, DESIGN, SEMICARBAZONES, PHENYTOIN
  • Eskisehir Osmangazi University Affiliated: Yes


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)-benzoxazolinone-3-acetyl hydrazide were synthesized. The chemical structures of the synthesized compounds were established by III, H-1-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)-benzoxazolinone-3-acetyl-2-(o-methoxy- benzaldehyde)-hydrazone 4d, 5-chloro2(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)-benzoxazolinone-3-acetyl-2-(p-nitrobenzaldehyde)-hydrazone 4m, and 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(p-dimethylamino- benzaldehyde)-hydrazone 4n were found more active than phenytoin (CAS 57-41-0) in the tests.