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Anticonvulsant and Toxicity Evaluation of Newer 4 H ‐Benzo[1,4]oxazin‐3‐ones: The Effect of Two Hydrogen Bonding Domains
Author(s) -
Siddiqui Nadeem,
Ali Ruhi,
Arshad M. Faiz,
Ahsan Waquar,
Ahmed Sharique,
Alam M. Shamsher
Publication year - 2010
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201000098
Subject(s) - chemistry , anticonvulsant , hydrazine (antidepressant) , stereochemistry , hydrogen bond , acute toxicity , neurotoxicity , toxicity , medicinal chemistry , pharmacology , molecule , organic chemistry , biochemistry , epilepsy , medicine , neuroscience , biology
Abstract A series of (Z) ‐2‐(substituted aryl) ‐N‐ (3‐oxo‐4‐(substituted carbamothioyl)‐3,4‐dihydro‐2 H ‐benzo[ b ][1,4]oxazin‐7‐yl) hydrazine carboxamides ( 6a–r ) was synthesized using 2‐amino‐5‐nitrophenol as a starting material. All the synthesized compounds possessed two hydrogen‐bonding domains and their effect on the activity was studied thereof. The anticonvulsant activity was assessed by the maximal electroshock test (MES), subcutaneous pentylenetetrazole test (scPTZ) and intraperitoneal thiosemicarbazide test (ipTSC). Compounds ( 6b , 6h , 6i , and 6p ) were found to be the most potent of the series as they showed 83–100% protection in the MES test. They also displayed considerable activity in the chemically induced seizure tests. Most of the tested compounds were devoid of the neurotoxic and hepatotoxic effects.