SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NOVEL SCHIFF BASES OF 2-QUINOLONES
Keywords:
2-Quinolones, Schiff base, Antibacterial activity, Antifungal activity, Antioxidant activity, Cytotoxicity activityAbstract
A series of novel substituted 3-acetyl-1-(benzylideneamino) quinolin-2(1H)-one (1-12) have been synthesized by condensing different substituted 3-acetyl-1-amino-quinolin-2-one and aromatic aldehydes in alcohol medium. 3-acetyl-1-amino-quinolin-2-one were synthesized from substituted 3-acetyl coumarin upon refluxing with hydrazine hydrate and ethanol. The structures of the final synthesized compounds were confirmed by IR, 1H NMR and mass spectra.The synthesized compounds were screened for their antimicrobial, antioxidant and cytotoxicity activities. The test compounds were screened for their antibacterial and antifungal activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Candida albicans, Aspergillus niger respectively by cup plate method. Compounds 2, 3, 5, 6, 7, 11 and 12 showed good antibacterial activity compared to the standard drug amoxicillin. Compounds 1, 2, 4, 5, 6, 8, 9, 10 and 12 showed moderate antifungal activity compared to the standard drug fluconazole.The antioxidant activity of the synthesised test compounds was done using DPPH radical scavenging method. Compounds 2 and 6 showed values at 85.78 and 13.41 respectively when compared to that of ascorbic acid at IC50 value of 3.69µg/ml and showed inhibitory concentration for 50% inhibition below 100 µg/ml. The final synthesized compounds were screened for their in vitro cytotoxicity activity against Ehrlich Ascites Carcinoma cells (EAC) by Trypan blue exclusion method. Compounds 2, 6 and 7 induced the greatest effect on EAC cells with an activity more than 60% at a concentration of 250µg/ml. Hence novel schiff bases synthesized from 2-quinolones are found to be interesting lead molecules as antimicrobial, antioxidant and cytotoxicity agents.
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