SINTEZA ȘI CERCETAREA PROPRIETĂȚILOR BIOLOGICE ALE UNOR DERIVAȚI AI 4-AMINO-5-METIL-4H-1,2,4-TRIAZOLULUI-3-TIOL

Abstract

În prezenta lucrare a fost realizată sinteza 1,1-dimetil-3-(3-metil-5-sulfanil-4H-1,2,4-triazol-4-il)tioureei (5) şi a 1,1-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-2-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 3 a fost efectuată difracţia cu raze X în monocristal.SYNTHESIS AND STUDY OF BIOLOGICAL PROPERTIES OF NEW4-AMINO-5-METHYL-4H-1,2,4-TRIAZOLE-3-THIOL DERIVATIVESIn 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 6 and 2 have MIC 0.007 mg/mL and 0.06 mg/mL respectively. The thiourea 6 has 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 3 was studied by conducted single-crystal X-ray diffraction.

Keywords

• 1,2,4-triazole, antiproliferative, cancer cells, Schiff base, antibacterial.