Synthesis, Characterization and Screening for Analgesic and Anti-inflammatory activities of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives.
2015
The aim of the present investigation was to synthesize, characterize and evaluate
analgesic and anti- inflammatory activities of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives.
The reaction of starting material 4-chloro-m-cresol with ethyl chloroacetate in dry
acetone affords ethyl (4-chloro-3-methylphenoxy) acetate, which after reacting with the hydrazine
hydrate in ethanol yields 2(4-chloro-3-methylphenoxy) acetohydrazide. When
2(4-chloro-3-methylphenoxy) acetohydrazide was treated with different aromatic aldehydes, aromatic acids
and carbon disulfide in alcoholic solution, different 3-acetyl-5-[(4-chloro-3-methylphenoxy) methyl]-2-aryl-2,
3-dihydro-1, 3, 4-oxadiazole and 2-[(4-chloro-3-methylphenoxy) methyl]-5-aryl-1, 3, 4-oxadiazole derivatives
were obtained. Purity of the derivatives was confirmed by thin layer chromatography and melting point.
Structure of these derivatives was set up by determining infrared spectroscopy, nuclear magnetic resonance
spectroscopy and mass spectroscopy. Further, the synthesized derivatives were evaluated for their analgesic
and anti-inflammatory activities in rodents. In animal studies, the derivatives 3-acetyl-5-[(4-chloro-3-
methylphenoxy)methyl]-2-(4-methoxyphenyl)-2,3-dihydro-1, 3, 4-oxadiazole and 4-{5-[(4-chloro-3-
methylphenoxy)methyl]-1, 3, 4-oxadiazol-2-yl}pyridine show more potent analgesic activity and the derivatives
2-{3-acetyl-5-[(4-chloro-3-methylphenoxy)methyl]-2,3-dihydro-1, 3, 4-oxadiazol-2-yl}phenol and 3-acetyl-5-
[(4-chloro-3-methylphenoxy)methyl]-2-(4-methoxyphenyl)-2,3-dihydro-1, 3, 4-oxadiazole exhibit more potent
anti-inflammatory effect as compared to other derivatives. The results of the current study indicate that cyclization
of acetohydrazide produces novel oxadiazole derivatives with potent analgesic and anti-inflammatory
activities.
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