Antioxidant and Antimicrobial Activities of Some Newly Synthesized 4-[1- (2,6-Dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4- triazol-5-on-4-yl-azomethine]-2-methoxyphenyl benzoates

Abstract

In this study, 4-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-2-methoxyphenyl benzoates were treated with 2,6-dimethylmorpholine in the presence of formaldehyde according to the Mannich reaction to synthesize six novel 4-[1-(2,6-dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-triazol-5-on-4-yl-azomethine]-2-methoxyphenyl benzoates. The structures of synthesized six novel heterocyclic compounds were characterized by IR, ¹³C-NMR and ¹H-NMR spectroscopic methods. The novel 4-[1-(2,6-dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-triazol-5-on-4-yl-azomethine]-2-methoxyphenyl benzoates were investigated in vitro antioxidant properties by using reducing power, free radical scavenging and metal chelating activity. For the measurement of the reductive ability, Fe³⁺-Fe²⁺ transformation was investigated in the presence of compound using by the method of Oyaizu (1986). The hydrogen atoms or electrons donation ability of the synthesized compound was measured by DPPH^. using the method of Blois (1958). The chelating effect of ferrous ions by the compound was determined according to the method of Dinis, Madeira & Almeida (1994). BHT, BHA, EDTA and α-tocopherol were used as reference antioxidant compounds. The new compounds were examined in-vitro antimicrobial properties against 6 different microorganisms (Bacillus substilis (ATCC11774), BacilluscCereus (ATCC11778), Staphylococcus aureus (ATCC6538), Escherichia coli (ATCC25922), Pseudomonas aeruginosa (ATCC27853) and Klebsiella pneumonia (ATCC4352)) by the agar well method and the obtained results were evaluated. 

Keywords

• Mannich base
• 4
• 5-dihydro-1H-1
• 2
• 4-triazol-5-one
• Antioxidant
• Antimicrobial

References

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