Combating oxidative stress in epilepsy: design, synthesis, quantum chemical studies and anticonvulsant evaluation of 1-(substituted benzylidene/ethylidene)-4-(naphthalen-1-yl)semicarbazides.

Abstract

A series of 1-(substituted benzylidene/ethylidene)-4-(naphthalen-1-yl)semicarbazides (3a-19a; 3b-6b) were synthesized in good yield and evaluated for their anticonvulsant and antioxidant activities. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. All of the compounds were found to be active in MES and scPTZ tests. Quantum chemical studies were carried out on these compounds to understand the structural features essential for activity. Electronic properties were found to be the principal modulator of both anticonvulsant and antioxidant activities. A computational study was carried out for prediction of pharmacokinetic properties and none of the compounds violated Lipinski's rule of 5, making them potentially promising agents for the treatment of epilepsy.

• Authors: Faizul Azam, Bashir A El-Gnidi, Ismail A Alkskas
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 45 Issue 7 Pg. 2817-26 (Jul 2010) ISSN: 1768-3254 [Electronic] France
• PMID: 20356656 (Publication Type: Journal Article)
• Copyright: Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.

Chemical References

• Anticonvulsants
• Antioxidants
• Benzylidene Compounds
• Semicarbazides

Topics

• Animals
• Anticonvulsants (chemical synthesis, chemistry, pharmacology, therapeutic use)
• Antioxidants (chemical synthesis, chemistry, pharmacology, therapeutic use)
• Benzylidene Compounds (chemistry)
• Drug Design
• Electrons
• Epilepsy (diet therapy, metabolism)
• Male
• Mice
• Oxidative Stress (drug effects)
• Quantum Theory
• Semicarbazides (chemical synthesis, chemistry, pharmacology, therapeutic use)