Arzneimittelforschung 2001; 51(7): 523-528
DOI: 10.1055/s-0031-1300075
CNS-active Drugs · Hypnotics · Psychotropics · Sedatives
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and Evaluation of Anticonvulsant Activities of Some New Arylhexahydropyrimidine-2,4-diones

Ünsal Çahş
Hacettepe University, Faculty of Pharmacy, Pharmaceutical Chemistry Department, Ankara, Turkey
Meriç Köksal
Hacettepe University, Faculty of Pharmacy, Pharmaceutical Chemistry Department, Ankara, Turkey
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26. Dezember 2011 (online)


In this study, some new 3-alkyl-6-arylhexahydropyrimldine-2,4-dione derivatives were synthesized as anticonvulsant agents. 6-Arylhexahydropyrimidine-2,4-diones which were used as starting materials in the synthesis of the compounds were prepared in acidic media by the cyclization of potassium cyanate and the appropriate ureido acids that were gained by the reaction of β-aminoacids, malonic acid and ammonium acetate. The structures of the synthesized compounds were confirmed by UV, IR, 1H-NMR and elementary analysis. Their anticonvulsant activities were determined by maximal electroshock (MES), subcutaneous metra-zol (scMet) and rotorod toxicity tests for neurological deficits. According to the activity studies, 3-arylalkyl-6-(p-chloro-phenyl) derivatives were found to be protective against scMet, whereas 6-phenyl derivatives were not 6-Phenyl-3-(2-mor-pholinoethyl)hexahydropyrimidine-2,4-dione was the only compound determined to be active against MES at 300 mg/kg dose at half an hour.


Synthese und Bewertung der antikonvulsiven Aktivität von neuen Arylhexahydro-pyrimidin- 2,4- dionen

In dieser Arbeit wurden einige neue Derivate von 3-Alkyl-6-arylhexahydropy-rimidin-2,4-dion hergestellt. 6-Arylhexa-hydropyrimidin-2,4-dione wurden durch Zyclisierung von Kaliumcyanid mit den entsprechenden Ureidosäuren in saurer Lösung synthetisiert. Die Ureidosäuren wurden durch Reaktion von β-Aminosäuren mit Malonsäure und Ammoniumacetat hergestellt. Die Strukturaufklärung der synthetisierten Verbindungen erfolgte mittels UV-, IR-, 1H-NMR-Spektroskopie sowie Elementaranalyse. Die antikonvulsive Aktivität wurde in MES- (maximaler Electroschock), ScMet- (subkuta-nes Metrazol) und Rotorod- Toxizitäts-Tests bestimmt. Die 3-Arylakyl-6-(p-chlo-rophenyl)-Derivate waren im MES-Test wirksam, während die 6-Phenyl-Derivate unwirksam waren. 6-Phenyl-3-(2-mor-pholinoethyl)hexahydropyrimidin-2,4-dion war als einzige Verbindung im MES-Test wirksam in einer Dosis von 300 mg/ kg in 30 min.