Tehran University of Medical Sciences
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Abbas Shafiee

Design and synthesis of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles as benzodiazepine receptor agonists.


Authors: Zarghi A , Faizi M , Shafaghi B , Ahadian A , Khojastehpoor HR , Zanganeh V , Tabatabai SA , Shafiee A ,
Bioorganic & medicinal chemistry letters , Vol., No. 0960-894X (Print) , 20050531 ,Page:0
A series of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles was designed and synthesized as anticonvulsant agents. Conformational analysis and superimposition of energy minima conformers of the designed molecules on estazolam, a known benzodiazepine receptor agonist, revealed that the main proposed benzodiazepine pharmacophores were well matched. Electroshock and pentylenetetrazole-induced lethal convulsion tests showed that the introduction of an amino group in position 2 of 1,3,4-oxadiazole ring and a fluoro substituent at para position of benzylthio moiety had the best anticonvulsant activity. It seems this effect is mediated through benzodiazepine receptors mechanism.