Abstract
A series of arylazopyrazolones 14-19 was synthesized through treatment of the 3-aminopyrazolin-5-one 13 with the appropriate diazonium salts 7-12, followed by cyclization of the resulted arylazopyrazolones 14, 19, and 23 with acetylacetone 20 in boiling acetic acid. Using doxorubicin as the reference drug, the in vitro cytotoxic activity of the synthetic arylazopyrazoles 14-19 and 21-23 was evaluated on four human cell lines. The results revealed that compounds 14-19 revealed good cytotoxic activity toward HepG2, HCT-116, MCF-7, and PC3 cell lines, within IC50 5.89 +/- 0.4-19.23 +/- 1.6; 7.15 +/- 0.6-23.15 +/- 1.8; 4.93 +/- 0.4-24.35 +/- 1.9; and 9.14 +/- 0.8-32.09 +/- 2.0 mu g/ml. The derivatives 15-17 displayed accurate anticancer activity toward all most cancers cell lines, even as compounds 22 exhibited moderate activities, while the pyrazolopyrimidine 21 has lower anticancer activity.