Sinteza şi cercetarea proprietăţilor biologice ale unor derivaţi ai 4-amino-5-metil-4H-1,2,4-triazolului-3-tiol [Articol]

Abstract

În prezenta lucrare a fost realizată sinteza1,1-dimetil-3-(3-metil-5-sulfanil-4H-1,2,4-triazol-4-il)tioureei (5) şi a1,1-dimetil-3-[3-metil-5-(metilsulfanil)-4H-1,2,4-triazol-4-il]tioureei (6), ale căror structuri au fost stabilite cu ajutorul spectrelor 1H-RMN şi 13C-RMN. Pe celule de cancer cervical substanţele iodhidrat de 3-metil-5-(metilsulfanil)-4H-1,2,4-triazol-4-amină 2) şi 6 au demonstrat o activitate nesemnificativă. Disulfura de tetrametiltiuram(DTMT) a demonstrat rezultate antibacteriene bune CMI 0,0007 mg/mL,iar substanţele 6 şi 2 au CMI 0,007 mg/mL şi, respectiv, 0,06 mg/mL. Tioureea 6 are proprietăţi antioxidante IC50= 29 μM/L aproximativ egale cu ale troloxului.A fost realizată sinteza N-[4-(3-metil-7H-1,2,4]triazolo[3,4-b][1,3,4]-tiadiazin-6-il)fenil]-2-[1-(piridin--il)etiliden]hidrazincarbotioamidei (11) şi a bazei Schiff [{[3-metil-5-(metilsulfanil)-4H-1,2,4-triazol-4-il]imino}metil]fenol (3). La compusul 3a fost efectuată difracţia cu raze X în monocristal.

In the present work the synthesis of 1,1-dimethyl-3-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)thiourea (5) and 1,1-dimethyl-3-[3-methyl-5 -(methylsulfanyl)-4H-1,2,4-triazol-4-yl]thiourea (6) was carried out. The structures were determined using 1H; 13C-NMR spectra. For cells HeLa of cervical cancer, substances 3-methyl-5-(methylsulfanyl)-4H-1,2,4-triazol-4-aminohydroiodide (2) and 6 have demonstrated not pronounced activity. Tetramethylthiuram disulfide (DTMT) showed good antibacterial activity MIC 0.0007 mg/mL, but substances 6and 2have MIC 0.007 mg/mL and 0.06 mg/mL respectively. The thiourea 6has antioxidant properties IC50= 29 μM/L approximately equal to trolox. Synthesis of N-[4-(3-methyl-7H[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazin-6-yl)phenyl]-2-[1-(pyridin-2-yl)ethylidene] hydrazinecarbothioamide (11) and Schiff base: 2-[{[3-methyl -5-(methyl-sulfanyl)-4H-1,2,4-triazol-4-yl]imino}methyl]phenol (3) was carried out. The compound 3was studied by conducted single-crystal X -ray diffraction.