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Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives

Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conform...

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Autores principales: Tabatabai, Sayyed Abbas, Barghi Lashkari, Saoka, Zarrindast, Mohammad Reza, Gholibeikian, Mohammadreza, Shafiee, Abbas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Shaheed Beheshti University of Medical Sciences 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813377/
https://www.ncbi.nlm.nih.gov/pubmed/24250678
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author Tabatabai, Sayyed Abbas
Barghi Lashkari, Saoka
Zarrindast, Mohammad Reza
Gholibeikian, Mohammadreza
Shafiee, Abbas
author_facet Tabatabai, Sayyed Abbas
Barghi Lashkari, Saoka
Zarrindast, Mohammad Reza
Gholibeikian, Mohammadreza
Shafiee, Abbas
author_sort Tabatabai, Sayyed Abbas
collection PubMed
description Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conformers of the compounds on estazolam, a known benzodiazepine agonist, reveal that the main proposed benzodiazepine pharmacophores were well matched. Anticonvulsant activity of the synthesized compounds, determined by pentylenetetrazole-induced lethal convulsion test, showed that the introduction of an amino substituent in position 5 of 1,3,4- oxadiazole ring generates compound 9 which has a respectable effect. The results are in agreement with SAR of benzodiazepine receptor ligands since the elimination of electronegative substituent in position 2 of phenoxy ring or position 4 of phenyl ring reduces the anticonvulsant activity.
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spelling pubmed-38133772013-11-18 Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives Tabatabai, Sayyed Abbas Barghi Lashkari, Saoka Zarrindast, Mohammad Reza Gholibeikian, Mohammadreza Shafiee, Abbas Iran J Pharm Res Original Article Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conformers of the compounds on estazolam, a known benzodiazepine agonist, reveal that the main proposed benzodiazepine pharmacophores were well matched. Anticonvulsant activity of the synthesized compounds, determined by pentylenetetrazole-induced lethal convulsion test, showed that the introduction of an amino substituent in position 5 of 1,3,4- oxadiazole ring generates compound 9 which has a respectable effect. The results are in agreement with SAR of benzodiazepine receptor ligands since the elimination of electronegative substituent in position 2 of phenoxy ring or position 4 of phenyl ring reduces the anticonvulsant activity. Shaheed Beheshti University of Medical Sciences 2013 /pmc/articles/PMC3813377/ /pubmed/24250678 Text en © 2013 by School of Pharmacy, Shaheed Beheshti University of Medical Sciences and Health Services This is an Open Access article distributed under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Tabatabai, Sayyed Abbas
Barghi Lashkari, Saoka
Zarrindast, Mohammad Reza
Gholibeikian, Mohammadreza
Shafiee, Abbas
Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives
title Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives
title_full Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives
title_fullStr Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives
title_full_unstemmed Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives
title_short Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives
title_sort design, synthesis and anticonvulsant activity of 2-(2-phenoxy) phenyl- 1,3,4-oxadiazole derivatives
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813377/
https://www.ncbi.nlm.nih.gov/pubmed/24250678
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