Synthesis and Biological Activities of Novel 1,2,4-Triazole Triazene Derivatives

Sixteen novel 1,2,4-triazole triazene derivatives were synthesized in multiple steps from the p-aminobenzoic acid. Their structures were confirmed by H-1 NMR, C-13 NMR and FIRMS. All the target compounds were evaluated for their anticancer activity. Among them, 2-[4-(3,3-dimethyltriazol-1-yl)phenyl]-3-amino-4-S-(4-chlorobenzyl)-1,2,4-triazole (6g), 2-[4-(3,3-dimethy ltriazol-1-yl)phenyl]-3-amino-4-S-(2,4-dichlorobenzyl)-1,2,4-triazole (6h), 2-[4-(3,3-methylbenzyltriazen-1-yl)-phenyl]-3-amino-4-S-benzyl-1,2,4-trioxazole (6i), 2-[4-( 3,3-methylbenzyltriazen-1-yl)-phenyl]-3-amino-4-S-(4-methylbenzyl)-1,2,4-triazole (6j), 2-[4-( 3,3-methylbenzy ltriazen-1-yl)phenyl]-3-amino-4-S-(4-methoxybenzyl)-1,2,4-triazole (6l), 2-[4-(3,3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(2,4-di-chlorobenzyl)-1,2,4-triazole (6p) exhibited good anti-cancer activity against J82 cells with the IC50 values of 23.883, 5.512, 8.731, 8.077, 5.590 and 12.195 mu mol/L, respectively. And compounds 6h, 6i, 6j, 6l exhibited good anti-cancer activity against DU145 cells with the IC50 values of 13.690, 21.908, 10.772 and 4.827 mu mol/L, respectively.