Synthesis, Biological and Acidic Properties of Some New 2-Ethoxy-4-[(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethine]-phenyl 2-Methylbenzoate Derivatives

Abstract

The synthesis of 2-ethoxy-4-[(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethine]-phenyl 2-methylbenzoates (4) from the reactions of 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) with 3-ethoxy-4-(2-methylbenzoxy)-benzaldehyde (3) is described. The acetylation reactions of compounds 4 were investigated, and 5 type N-acetyl derivatives were obtained and the newly synthesized compounds were fully characterized. Also, in vitro antibacterial activities of the fourteen new compounds were screened against six bacteria such as Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus cereus and Klebsiella pneumonia according to agar well diffusion method. In addition, the newly synthesized 14 novel compounds were tested for their antioxidant activities using three different methods. Furthermore, to investigate the effects of solvents and molecular structure upon acidity, the compounds 4 were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, N,N-dimethylformamide and acetone).