Claisen-Schmidt condensation reaction were undertaken for synthesizing four substituted chalcones 4ʹ– methyl – 4 – hydroxyl – 3 – methoxy chalcone (3a), 2ʹ – hydroxyl – 4 – methoxy – 3,4 – methylenedioxy chalcone (3b), 4ʹ–methyl – 2, 3, 4 – trimethoxy chalcone (3c), 4ʹ – benzyloxy – 2 – hydroxyl – 3,4 –methylenedioxy chalcone (3d) and characterized by spectral data. As the number of electrons donating auxochromes increase the color of the compound also deepens. In search of the potency as new antibiotic or chemotherapeutic agents in vitro antimicrobial screening of the synthesized chalcones (3a-3d) were done against seven pathogenic bacteria by disc diffusion technique. Compounds are more sensitive against G organism than that of G+ organism at the concentration 250 µg/disc comparing to those of the standard drug (amoxicillin, 40µg/disc). In addition compound 3b showed highest antioxidant activity, IC50 is 12.15 (µg/mL) in diphenylpicrylhydrazin (DPPH) model. The compound 3b contains phenolic –OH group in ortho position and suppose to produce phenoxide free radical easily which can be stabilized by electronic group methoxy occupied para position of aromatic ring (A) attached to another aromatic ring containing methylenedioxy moiety.
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