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SM ISO690:2012 RUSNAC, Anna, RUSNAC, Roman, GARBUZ, Olga, GULYA, Aurelian. Derivatives of 3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-amine with antimicrobial and antioxidantives properties. In: Ecological and environmental chemistry : - 2017, Ed. 6, 2-3 martie 2017, Chișinău. Chisinau, Republic of Moldova: Academy of Sciences of Moldova, 2017, Ediția 6, p. 224. |
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Ecological and environmental chemistry Ediția 6, 2017 |
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Conferința "Ecological and environmental chemistry 2017" 6, Chișinău, Moldova, 2-3 martie 2017 | |||||||
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Pag. 224-224 | |||||||
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Recently the chemistry of triazoles and their derivatives received considerable attention due interesting their synthesis and important biological activity. Triazole compounds of groups N,N- dimethyl eurydice in the literature are lacking. The literature investigation shows that derivatives 1,2,4-triazole presents a wide range of biological activities including antiproliferative, antibacterial, antituberculosis. We have aimed at the synthesis of 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea and 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea research to determine the structure and biological properties. The dependence of yield of 1,1-dimethyl-3- (3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl) thiourea and 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea was investigated in dependence of factors different. It was found that 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol to tetramethylthiuram disulfide (TETD) heating at a molar ratio of 1:1.1 for eight hours at 100-105 0C leads to 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea with a yield of 83%. 3-Methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-amine under similar conditions gave a yield of 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea only 57%. A great difference in yields a may be explained by the steric difficulties arising from 3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-amine in reaction with TETD, were the SH group is replaced by SCH3. When 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea and 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea are treated with iodomethane expected the formation of S-methylisothiourea expected. Analisis of these reactions demonstrated that only 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea was methylated to the SH group, and the group C=S tioureide 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea and 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea remains unaffected, likely due to the steric factor. The structure of 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea and 1,1-dimethyl-3-[3-methyl-5-(methylsulphanyl-yl)-4H-1,2,4-triazol-4-yl]thiourea were confirmed by 1H, 13C-NMR and IR spectra. Antibacterial and antioxidantive properties of the parent compound were investigated TETD pas the important antibacterial activity MIC 0.0007 mg/mL, 3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-amine showed results of MIC 0.06 mg/mL and 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea has the respectively MIC 0.007 mg/mL. The antioxidant activity of 1,1-dimethyl-3-[3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea is IC50 = 29 μM like as Trolox with. |
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