Open AccessSynthesis, Characterization and Biological Activity of New Mefenamic acid - Oxoazetidine Derivatives
Author(s) -
Ayad M.R. Raauf
Publication year - 2013
Publication title -
almustansiriya journal of pharmaceutical sciences/al-mustansiriyah journal of pharmaceutical sciences
Language(s) - English
Resource type - Journals
eISSN - 2959-183X
pISSN - 1815-0993
DOI - 10.32947/ajps.v13i1.181
Subject(s) - mefenamic acid , chloroacetyl chloride , benzoic acid , chemistry , yield (engineering) , amination , chloride , antibacterial activity , hydrazine (antidepressant) , organic chemistry , amine gas treating , condensation reaction , ethanol , hydrate , medicinal chemistry , nuclear chemistry , catalysis , bacteria , chromatography , materials science , biology , metallurgy , genetics
Several new oxoazetidine derivatives based on mefenamic acid were synthesized via a four steps method in good yields.1st step was prepared 2-[2-chloro-N-(2,3- dimethylphenyl)acetamido]benzoic acid (2) by condensation of mefenamic acid with chloroacetyl chloride, which on amination with hydrazine hydrate in ethanol to give 2-[N- (2,3-dimethylphenyl)-2-hydrazinylacetamido] benzoic acid (3) in good yields(2nd step).Compound 3, on condensation with various aldehydes afforded a series of Schiff bases 2-[N- (2,3-dimethylphenyl)-2-(2-arylhydrazinyl)acetamido]benzoic acid (4a-f) (3rd step).A series of oxoazetidine have been synthesized by cyclocondensation of various Schiffm bases (4a-f) with chloroacetyl chloride or phenyl acetyl chloride in presence of triethyl amine to yield compounds (5a-f) and (6a-f), respectively (4th step). Purified compounds were characterized by mp, TLC, UV, FT-IR and elemental analysis.The synthesized compounds (5a-f) were screened for their antibacterial activities against three species of bacteria. They were found to exhibit good antibacterial activity.