Paper Information

Title: 

SYNTHESIS AND ANXIOLYTIC ACTIVITY OF 3-NITROPHTHALIMIDE DERIVATIVES

Type: POSTER
Author(s): HASANZADEH F.,RABANI M.,KHODA RAHMI GH.A.,FASIHI A.,ZARGAR H.R.
 
 
 
Name of Seminar: IRANIAN CONGRESS OF PHYSIOLOGY AND PHARMACOLOGY
Type of Seminar:  CONGRESS
Sponsor:  PHYSIOLOGY AND PHARMACOLOGY SOCIETY, MASHHAD UNIVERSITY OF MEDICAL SCIENCE
Date:  2007Volume 18
 
 
Abstract: 

Introduction: Benzodiazepins are widely used to relieve phobia and other major symptoms of anxiety. According to the SAR studies of benzodiazepins a flat aromatic structure containing an electron withdrawing group at proper position (C7 on ring A) is necessary. On the other hand barbiturates which are also used as anxiolytic agents have flat structures containing Imide functional groups. N-Benzoyl phethalimide which possess the flat ring system and the imide group was synthesized previously in this department and showed interesting anxiolytic effects. In this study some N-benzoyl phthalimide derivatives have been prepared to examine the substituent effects on anxiolytic activity.
Methods: Phthalic anhydride was first nitrated to produce a mixture of 3 and 4 nitrophthalic Acid. The resulting 3-nitro derivative was added to a mixture of urea and ethylenglycol-mono methyl ether and was refluxed to produce 3-nitrophthalimide. 3-Nitro derivative was then reacted with benzoyl chloride and para methyl benzoyl chloride to give N-benzoyl-3-nitrophthalimide (III), and N-para methyl benzoyl-3-nitrophethalimide (IV) respectively. Two doses (5, 10 mg/kg) of the test compounds, diazepam (1.5) mg/kg and the vehicle as control were injected subcutaneously to mice. After 0.5 hour, distribution of behavior on the EPM was calculated.
Results: Diazepam at the dose of 1.5 mg/kg significantly increased the time spent up to 62% in open arm. Among the compounds that were tested in this study only compound III at the dose of 10 mg/kg showed significant increase up to 58% in open arm time.
Conclusion: The low activity of compound III maybe due to the improper accommodation of the nitro group in the benzodiozepine active site. Substitution of electron donating groups on the C ring of the parent compound was also in favorable for anxiolytic activity.

 
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