Synthesis and anticancer activity of 3-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehydes

Abstract

The generation of heterocycles containing 1,2,3-triazole and pyrazole moieties has been explored. The synthesis of these heterocycles is of interest because they are components of important compounds ranging from agrochemicals to pharmaceuticals. Particularly interesting are their potential cancer cell anti-proliferation properties. Three 3-(5-methyl-1-aryl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehydes, where the aryl substituent is phenyl, 4-methoxyphenyl, or 4-nitrophenyl, have been used as precursors for the synthesis of new heterocycles. 1H-1,2,3-triazoles containing dithiols, acrylates, isoxazol-5(4H)-one, hydrazone, and bis-thiocarbohydrazone were synthesized in good yields from the precursors using simple procedures. The in vitro assessment of the activity of the resultant heterocycles against human cancer cells (HCT-116, HepG2, and MCF-7) and a human healthy cell line (BJ-1) was performed using the lactate dehydrogenase assay. Thiocarbohydrazone was the most active heterocycle, and its cytotoxic activity was comparable to that obtained for doxorubicin as a reference. The other heterocycles showed moderate cytotoxic activities.