Synthesis and characterization of some heterocyclic schiff bases: potential anticonvulsant agents
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- 作者：Shailendra Pandey (1)
R. S. Srivastava (1) - 关键词：Heterocyclic schiff bases ; 3 ; Aminomethyl pyridine ; Anticonvulsant activity ; Neurotoxicity
- 刊名：Medicinal Chemistry Research
- 出版年：2011
- 出版时间：September 2011
- 年：2011
- 卷：20
- 期：7
- 页码：1091-1101
- 全文大小：852KB
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R. S. Srivastava (1)
1. Pharmaceutical Chemistry Research Laboratory, Department of Pharmaceutics, Institute of Technology, Banaras Hindu University, Varanasi, 221005, India
文摘
A series of novel schiff bases of 3-aminomethyl pyridine have been synthesized through condensation reaction with substituted aryl aldehydes/ketones and/cyclic ketones. These schiff bases were screened for anticonvulsant activity. The chemical structures of synthesized compounds were confirmed by FT-IR, 1H-NMR, spectroscopy, and elemental analysis. A number of compounds were observed to exhibit seizures protection after intraperitoneal administration at the dose 30 and 100?mg?kg? in various models employed. In MES screen we found five potent compounds i.e., (1c) N-(2-chlorobenzylidene) (pyridin-3-yl) methanamine, (1f) 2-methoxy-4-{(pyridine-3-ylmethyl imino) methyl} phenol, (2a) N-(3phenylallylidene) (pyridin-3-yl) methanamine, (3b) 3-{1-(pyridin-3-ylmethylimino) ethyl} benzenamine, and (4a) N-(diphenyl-methylene) (pyridin-3-yl) methanamine, emerged as most active compounds in series (ED50) 11.70, 6.39, 11.70, 8.64, and 9.13?mg?kg? with high protective index (PI)?>?10. Four compounds (1e) 4-{(Pyridine-3-ylmethylmino) methyl}benzene-1,3-diol, (1g) N-(3,4,-dimethoxybenzylidene) (pyridin-3-yl)methanamine, (2b) N-{(1H-indol-3-yl)methylene}(pyridin-3-yl) methanamine, and (5) N-cyclohexylidene (pyridine-3-yl) methanamine) showed remarkable protection over clinically used drugs in sc.PTZ screen (ED50) 6.44, 11.70, 6.47, and 14.16 with (PI?>?10). Compound (4b) showed good anticonvulsant activity (ED50) 20.79, but with relatively higher neurotoxicity (PI, 0.57). Compound (1e) was active in both sc.PTZ and in sc.STR seizures. Some selected compounds were subjected to oral MES screen (30?mg?kg?) in rats, most of the compounds showed peak activity after 0.5?h of oral administration.