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Sci. Pharm. 2008, 76(2), 185-202; doi:10.3797/scipharm.0803-10 (registering DOI)

Synthesis and Pharmacological Evaluation of New 2-Substituted-5-{2-[(2-halobenzyl)thio)phenyl}-1,3,4-oxadiazoles as Anticonvulsant Agents

1
Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Beheshti University (M.C), Tehran, Iran
2
Pharmacology, Faculty of Pharmacy, Shahid Beheshti University (M.C), Tehran, Iran
3
Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
*
Author to whom correspondence should be addressed.
Received: 16 March 2008 / Accepted: 14 April 2008 / Published: 20 April 2008
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Abstract

A new series of 2-substituted-5-{2-[(2-halobenzyl)thio)phenyl}-1,3,4-oxadiazoles was designed, synthesized and investigated for anticonvulsant activities. The designed compounds contain the main essential pharmacophore for binding to the benzodiazepine receptors. Conformational analysis and superimposition of energy minima conformers of designed molecules on estazolam, a known benzodiazepine receptor agonist, revealed that the main characteristics of the proposed benzodiazepine pharmacophore were well matched. Electroshock and pentylenetetrazole-induced lethal convulsion tests showed that some of the synthesized compounds had significant anticonvulsant activity. The structure-activity relationship study of these compounds indicated that the introduction of an amino group at position 2 of 1,3,4-oxadiazole ring and a fluoro substituent at the ortho position of the benzylthio moiety had the best anticonvulsant activity. Anticonvulsant effects of active compounds were antagonized by flumazenil, a benzodiazepine antagonist, which establish the involvement of benzodiazepine receptors in these effects.
Keywords: Benzodiazepine receptor; 1,3,4-Oxadiazoles; Anticonvulsant; SAR Benzodiazepine receptor; 1,3,4-Oxadiazoles; Anticonvulsant; SAR
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

ZARGHI, A.; HAMEDI, S.; TOOTOONI, F.; AMINI, B.; SHARIFI, B.; FAIZI, M.; TABATABAI, S.A.; SHAFIEE, A. Synthesis and Pharmacological Evaluation of New 2-Substituted-5-{2-[(2-halobenzyl)thio)phenyl}-1,3,4-oxadiazoles as Anticonvulsant Agents. Sci. Pharm. 2008, 76, 185-202.

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