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Design, synthesis and biological activities of 5Hdibenzo[ b,f]azepine-5-carboxamide derivatives; Targeted hippocampal trypsin inhibition as a novel approach to treat epileptogenesis

Taha Iqbal
Mohsin Abbas Khan
Irshad Ahmad
Fahad Mehmood Khan


Purpose: To synthesize anticonvulsant drug derivatives that target protease-activated receptor generated epileptic seizures.
Method: Varieties of carbamazepine-based Schiff bases were designed with different aldehydes and ketones, and evaluated for in silico computer-aided drug design prediction of absorption, distribution, metabolism and excretion (ADME), and potential drug targets. The resultant compounds were synthesized and characterized by various spectroscopic techniques, including FTIR, 1H-NMR and 13CNMR, analysis. Thereafter, they were screened for antimicrobial, antioxidant and anticonvulsant potential.
Results: Prominent anti-protease potential was shown by C7 and C3 compounds and the order of activity was C7 > C3 > C5 > C2 > C6 > C4 > C2 > C1 (p < 0.05). The anticonvulsant activity of C7 and C5 was comparable with the standard drug; C3, C4, C6 and C8 had mild activity while C1 and C4 showed the least activity. The synthesized compounds exhibited significant (p < 0.05) antioxidant potential (rank order: C3 > C4 > C5 > C7 > C8 > C6 > C1 > C2) and antimicrobial activity against S.aureus and B. bronchiseptica (rank order: C5 > C2 > C8 > C1 > C4 > C3 > C7).
Conclusion: Synthesized derivatives retained their potential for anticonvulsant and antitrypsin activity, unlike their mother moiety, i.e., carbamazepine. The additional antibacterial activity effectively treats neurological disorders associated with bacterial infections.

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eISSN: 1596-9827
print ISSN: 1596-5996