Synthesis and biological evaluation of hydrazone and pyrazoline derivatives derived from androstenedione

Here, two series of 17-hydrazone derivatives and D-fused pyrazoline derivatives possessing various aromatic heterocycle structures from androstenedione were synthesized and their structures were evaluated. The antiproliferative activity of synthesized compounds against three cancer cells (446, Eca-109, AGS) and a normal cell line (GES-1) was investigated. Cisplatin was taken as the reference drug. The results have demonstrated that D-fused pyrazoline derivatives showed strong activity than 17-hydrazone derivatives. Compound 7b, bearing a phenyl group at 5′ in pyrazoline, inhibits the growth of Eca-109, 446 and AGS cells with IC50 = 17.5, 25.3, 27.4 μM, respectively. The corresponding IC50 of cisplatin is 30.4, 44.2, 36.7 μM. This suggests it is a potent apoptotic inducer in these carcinoma cells. Most of the compounds show very weak toxicity towards GES-1 normal cell line.