Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as anticonvulsant agents

Afshin Zarghi; Zahra Hajimahdi; Shohreh Mohebbi; Hootesa Rashidi; Sasan Mozaffari; Sahar Sarraf; Mehrdad Faizi; Seyed Abbas Tabatabaee; Abbas Shafiee

doi:10.1248/cpb.56.509

Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as anticonvulsant agents

Chem Pharm Bull (Tokyo). 2008 Apr;56(4):509-12. doi: 10.1248/cpb.56.509.

Authors

Afshin Zarghi¹, Zahra Hajimahdi, Shohreh Mohebbi, Hootesa Rashidi, Sasan Mozaffari, Sahar Sarraf, Mehrdad Faizi, Seyed Abbas Tabatabaee, Abbas Shafiee

Affiliation

¹ Department of Medicinal Chemistry, Shaheed Beheshti University of Medical Sciences, Tehran, Iran. [email protected]

PMID: 18379099
DOI: 10.1248/cpb.56.509

Abstract

A new series of 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles was designed and synthesized as anticonvulsant agents. Electroshock and pentylenetetrazole-induced lethal convulsion tests showed that the introduction of an amino group at position 2 of 1,3,4-oxadiazole ring and a fluoro substituent at ortho position of benzyloxy moiety had the best anticonvulsant activity. Our results showed that this effect is mediated through benzodiazepine receptors mechanism.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anticonvulsants / chemical synthesis*
Anticonvulsants / pharmacology*
Behavior, Animal / drug effects
Chemical Phenomena
Chemistry, Physical
Convulsants
Dose-Response Relationship, Drug
Drug Design
Electroshock
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mice
Models, Molecular
Oxadiazoles / chemical synthesis*
Oxadiazoles / pharmacology*
Pentylenetetrazole
Receptors, GABA-A / drug effects
Spectrophotometry, Infrared
Stereoisomerism
Structure-Activity Relationship

Substances

Anticonvulsants
Convulsants
Indicators and Reagents
Oxadiazoles
Receptors, GABA-A
Pentylenetetrazole