Synthesis and characterization of some heterocyclic schiff bases: potential anticonvulsant agents

Abstract

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, 1 H-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 -1 in various models employed. In MES screen we found five potent compounds i.e., (1 c ) N-(2-chlorobenzylidene) (pyridin-3-yl) methanamine, (1 f ) 2-methoxy-4-{(pyridine-3-ylmethyl imino) methyl} phenol, (2 a ) N-(3phenylallylidene) (pyridin-3-yl) methanamine, (3 b ) 3-{1-(pyridin-3-ylmethylimino) ethyl} benzenamine, and (4 a ) N-(diphenyl-methylene) (pyridin-3-yl) methanamine, emerged as most active compounds in series (ED 50 ) 11.70, 6.39, 11.70, 8.64, and 9.13 mg kg -1 with high protective index (PI) [ 10. Four compounds (1 e ) 4-{(Pyridine-3-ylmethylmino) methyl}benzene-1,3-diol, (1 g ) N-(3,4,-dimethoxybenzylidene) (pyridin-3-yl)methanamine, (2 b ) 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 (ED 50 ) 6. 44, 11.70, 6.47, and 14.16 with (PI [ 10). Compound (4 b ) showed good anticonvulsant activity (ED 50 ) 20.79, but with relatively higher neurotoxicity (PI, 0.57). Compound (1 e ) was active in both sc.PTZ and in sc.STR seizures. Some selected compounds were subjected to oral MES screen (30 mg kg -1 ) in rats, most of the compounds showed peak activity after 0.5 h of oral administration.

Design, Synthesis and Evaluation of Some New 4-Aminobenzoic Acid Derivatives as Potential Cognition Enhancer

“…The reaction progress was monitored by TLC using mobile phase as Ethyl acetate: Pyridine: Acetic acid: water (100:18.5:2.5:5) on completion of reaction, compounds were obtained by precipitation on addition of 10 ml ethylacetate and recrystallized by ethylacetate and absolute methanol. [20] 4-(2, 4, 6-Trihydroxybenzylidene amino) benzoic acid (1) …”

Synthesis (Z) vs (E) Selectivity, Antifungal Activity against Fusarium oxysporum, and Structure-Based Virtual Screening of Novel Schiff Bases Derived from l-Tryptophan

“…oxysporum, showing high biological activities . These antecedents have inspired us to continue studying the derivatization of amino acids adding imine and/or enamine group as pharmacophore, , using conventional reactions toward an eco-friendly protocol with a slight environmental impact, taking advantage of the Schiff condensation reaction. − From medicinal and pharmaceutical perspectives, Schiff bases have demonstrated a potential interest due to their demonstrated biological activities such as anti-inflammatory, , analgesic, , antimicrobial, ,,, anticonvulsant, , antituberculous, anticáncer, antioxidant, , anthelmintic, antiviral, and antifungal. ,− Many Schiff bases have also been used as substrates to prepare numerous biologically active compounds, becoming interesting precursors in organic syntheses. Recently, a series of chitosan derivatives , were successfully synthesized via the Schiff reaction employing aldehydes with a high degree of substitution, among those bearing active halogenated aromatic imines.…”

Synthesis, Characterization and Biological Activities of Binuclear Metal Complexes of 2-Benzoylpyridine and Phenyl(Pyridin-2-yl) Methanediol Derived from 1-Phenyl-1-(Pyridin-2-yl)-N-(Pyrimidin-2-yl) Methanimine Dihydrate Schiff Base

“…Heterocyclic Schiff base ligands containing O-or N-donors and their metal complexes have been shown to exhibit interesting properties [1] [2] [3] and those containing pyrimidine and pyridine rings represent a promising class of compounds due to their inherent biological and pharmaceutical properties [2] [3] [4] [5]. Pyrimidine and pyridine based compounds exhibit a broad spectrum of biological activities [6] [7].…”