| Abstract [eng] |
Compounds which contains azole fragments are important because of their biological and pharmacological properties. These compounds have antimicrobial, antioxidant, anticancer, analgesic, antivirus properties, which are applied in medical and agrochemical industry. In this work 3-[(4-methoxyphenyl)(phenylcarbamoylthio)amino]-N-[(phenylcarbamoylthio)amino]propanamide acidic cyclization reaction was performed, synthesizing 3-(4-methoxyphenyl)-1phenyl-3-{2-[5-(phenylamino)-1,3,4-thiadiazol-2-yl]ethyl}thiourea. N-Alkylated derivatives were obtained by performing 3-{2-[(4-methoxyphenyl)amino]ethyl}-4-phenyl-4,5-dihydro-1H-1,2,4triazol-5-one alkylation reactions with 2-bromoacetophenone and 2-bromo-4'-fluoroacetophenone. SSubstituted 1,2,4-triazol-5-thiones derivatives were obtained by performing 3-{2-[(4methoxyphenyl)amino]ethyl}-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-thione S-alkylation reactions in acetone, alkaline medium. N-Acylation reactions of 3-{2-[(4-methoxyphenyl)amino]ethyl}-4phenyl-4,5-dihydro-1H-1,2,4-triazol-5-thione and 2-[(5-{2-[(4-methoxyphenyl)amino]ethyl}-4phenyl-4H-1,2,4-triazol-3-yl)thio]-1-(4-methylphenyl)ethan-1-one with acetyl chloride were also performed. The structures of synthesized compounds were confirmed by 1H NMR, 13C NMR, IR spectroscopy and mass spectrometry methods. Antioxidant and antibacterial activity of the synthesized compounds were examined. The examination revealed that N-alkylated 3-{2-[(4-methoxyphenyl)amino]ethyl}-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-ones had the strongest antioxidant properties. Of azole fragment containing compounds 3(2-{[2-(4-fluorophenyl)-2-oxoethyl](4-methoxyphenyl)amino}ethyl)-4-phenyl-4,5-dihydro-3H1,2,4-triazol-5-one showed the strongest antibacterial effect against Escherichia coli and Rhizobium radiobacter bacteria and N-(4-methoxyphenyl)-N-[2-(5-{[2-(4-methylphenyl)-2-oxoethyl]thio}-4phenyl-4H-1,2,4-triazol-3-yl)ethyl]acetamide showed the strongest antibacterial effect against Xanthomonas campestris bacteria. |
