Synthesis and anticonvulsant evaluation of some novel (thio)semicarbazone derivatives of arylalkylimidazole

Abstract A number of novel 2-(1 H -imidazole-1-yl)-1-aryl-substituted ethane-1-one N-substi-tuted phenyl(thio)semicarbazones (1-14) were synthesized to test for their anticonvulsant activity against the two seizure models, maximal electroshock (MES) and subcutaneous pentylenetetrazol (scPTZ). Title...

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Bibliographic Details
Published in:	Arzneimittel-Forschung Vol. 61; no. 6; pp. 327 - 334
Main Authors:	Çaliş, Ünsal, SeptioğluEbubekir, Septioğlu, Aytemir, Mutlu Dilsiz
Format:	Journal Article
Language:	English
Published:	Aulendorf (Germany) Editio Cantor Verlag 01-01-2011 Thieme
Subjects:	Animals Anticonvulsants - chemical synthesis Anticonvulsants - pharmacology Biological and medical sciences CNS-active Drugs Convulsants Electroshock Hypnotics Imidazoles - chemical synthesis Imidazoles - pharmacology Indicators and Reagents Magnetic Resonance Spectroscopy Male Medical sciences Mice Pentylenetetrazole Pharmacology. Drug treatments Postural Balance - drug effects Psychotropics Sedatives Seizures - chemically induced Seizures - prevention & control Semicarbazones - chemical synthesis Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Infrared Structure-Activity Relationship Thiosemicarbazones - chemical synthesis Thiosemicarbazones - pharmacology Anticonvulsant activity Arylalkylimidazole Semicarbazone Synthesis Thiosemicarbazone Evaluation Anticonvulsant
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Summary:	Abstract A number of novel 2-(1 H -imidazole-1-yl)-1-aryl-substituted ethane-1-one N-substi-tuted phenyl(thio)semicarbazones (1-14) were synthesized to test for their anticonvulsant activity against the two seizure models, maximal electroshock (MES) and subcutaneous pentylenetetrazol (scPTZ). Title compounds were prepared by the reaction of appropriate (thio)semicarba-zides with ketones. Neurotoxicity was screened by the rotarod test. The structure of compounds was confirmed by elemental analysis results and the spectroscopic techniques such as IR, 1 H-NMR, 13 C-NMR, ESI-MS and HRMS. As a result of activity studies, when the thiosemicar-bazone compounds were compared at different doses, 2-(1H -imidazole-1-yl)-1-(2-naphthyl)ethane-1-one N -(3-chloro-phenyl)thiosemicarbazone (3) and 2-(1 H -imidazole-1-yl)-1-(2-biphenyl)ethane-1-one N -(4-fluorophenyl)thiosemicarba-zone (12) were found selective and highly active compounds against MES-induced seizures after 0.5 h and 4 h, respectively. Beside this, 2-(1 H -imidazole-1-yl)-1-(1-biphenyl)ethane-1-one N -(4-methylphe-nyl)thiosemicarbazone (14) was the most active compound in the scPTZ-induced seizure test after 4 h. The 2,4-dichloro-phenyl (9) and 2-fluorophenyl (10) substituted biphenyl derivatives of thiosemi-carbazone compounds showed neurotoxicity at higher doses
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1
ISSN:	0004-4172 1616-7066
DOI:	10.1055/s-0031-1296206