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SYNTHESIS AND INVESTIGATIONS OF ANTIMICROBIAL, ANTIOXIDANT ACTIVITIES OF NOVEL DI-[2-(3-ALKYL/ ARYL-4, 5-DIHYDRO-1H-1, 2, 4-TRIAZOL-5-ONE-4-YL)- AZOMETHINEPHENYL] ISOPHTALATES AND MANNICH BASE DERIVATIVES

HAYDAR YÜKSEK, GÜL ÖZDEMİR, SEVDA MANAP, YONCA YILMAZ, GÜL KOTAN, ÖZLEM GÜRSOY-KOL, MUZAFFER ALKAN

Acta Pharmaceutica Sciencia - 2020;58(1):49-68

Kafkas University, Department of Chemistry, Chemistry, Kars, Turkey

 

In this study, the synthesis of di-[2-(3-alkyl/aryl-4, 5-dihydro-1H-1, 2, 4-triazol- 5-one-4-yl)-azomethinephenyl] isophtalates (2a-g) from the reactions of 3-alkyl/ aryl-4-amino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones (1a-g) with di-(2-formylphenyl) isophtalate is described. Then, the compounds 2 were treated with morpholine in the presence of formaldehyde to synthesize di-{2-[1-(morpholine-4-yl-methyl)-3- alkyl(aryl)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one-4-yl]-azomethinephenyl} isophtalates (3a-g). The newly synthesized compounds were characterized using IR, 1HNMR and 13C-NMR spectral data. In addition, the compounds synthesized were screened for their antimicrobial activities. Furthermore, the antioxidant properties of the newly synthesized compounds were analysed for their in-vitro potential antioxidant activities in three different methods (reducing power, free radical scavenging and metal chelating activity). These antioxidant activities were compared to those from standard antioxidants, such as BHA, BHT, EDTA and α-tocopherol.