Bis[(3,5-dimethyl pyrazol)-1-yl Thiocarbonyl)] Disulfide

Abstract

This experiment is performed according to literature method [1][2][3][4]. 3,5-Dimethyl pyrazole 1 (2,3 g; 0.024 mole) in ethanol solution and triethylamine (6.65 g, 0.048 mole) were cooled to 5°C under stirring, then carbon disulfide (3.65 g, 0.048 mole) was added to the solution. After 1 hour of stirring, solid iodine (2,8 g, 0.022 mol) was added in portions and stirred until the colour disappeared completely. Then a methanolic solution of iodine was added dropwise until a faint colour persists. Excess of iodine was neutralised with Na 2 S 2 O 3 solution. The product was extracted with diethyl ether, washed thrice with water, dried over Na 2 SO 4 , filtered, and diethyl ether was evaporated at room temperature to give compound 2 as a white solid. Yield: 93%.Mp.: 87-89°C (diethyl ether/hexane: 8/2).1 H-NMR (CDCl 3 ) d (ppm): 2,43 (s, 12H, CH 3 ); 6,00 (s, 2H, H pyrazole ). 13 C-NMR(CDCl 3 ) d :193 ppm (-C=S), 150 (C 3 ), 148 (C 5 ), 110 (C 4 ), 12 (CH 3 ). IR (KBr , cm -1 ) : 3000 (-S-S-); 1290 (C=S). MS (m/z): 342 [M] + . U.V.: l max = 285 nm (-C=S).

Anticancer Activities of bis(pyrazol-1-ylthiocarbonyl)disulfides against HeLa cells

“…Literature compounds, pyrazol-1yldithiocarbamate (1) and 3,5-dimethylpyrazol-1-yldithiocarbamate (2), were prepared according to literature methods. 15,16 As for the known bis(3,5-dimethylpyrazol-1-yldithiocarbonyl)disulfide (5), a different synthetic procedure from the one reported in the literature 17 was employed. All experiments were performed under dry, deoxygenated nitrogen atmosphere using Schlenk techniques.…”

“…Iodine oxidation of the appropriate dithiocarbamate salts {pyrazol-1-yldithiocarbamate (1), 3,5-dimethylpyrazol-1yldithiocarbamate (2) 15,16 or indazol-1-yldithiocarbamate (3)} produced one known (5) 17 and two new (4 and 6) bis (dithiocarbonyl)disulfides as yellow powders in moderate yields (Scheme 1). Except for 6, compounds 4 and 5 were readily soluble in chlorinated solvents.…”