Synthesis, antitumor, cytotoxic and antioxidant evaluation of some new pyrazolotriazines attached to antipyrine moiety

Iminopropanehydrazonoyl cyanide 4 was achieved upon reaction of antipyrine diazonium salt 2 with 3-iminobutanenitrile (3) in EtOH/AcONa. 3-Aminopyrazole derivative 5 was obtained upon reaction of 4 with hydrazine hydrate. Diazodization of 5 afforded the diazonium salt 6 which coupled with active methylene compounds 7–10, 19, 20, 25, 29 and 32 in pyridine to give aryl hydrazone derivatives 11–14, 21, 22, 26, 30 and 33, respectively. Refluxing of compounds 11–14, 21, 22, 26 and 33 in acetic acid afforded the pyrazolotriazines 15–18, 23, 24, 28 and 35, respectively. The newly synthesized compounds were screened for their cytotoxic and antioxidant activities. The results showed clearly that compounds 4, 5, 13, 22, and 24 displayed promising in vitro anticancer activity against four different cell lines (HepG2, WI 38, VERO and MCF-7). Compounds 4 and 22 are the more potent antioxidant and anticancer agents. On the other hand, most of the compounds exhibited good cytotoxic activity toward (EAC).

Graphical abstractNewly synthesized pyrazole derivatives were established on the basis of elemental analyses, spectral data and screened for their antitumor and antioxidant activities. Some of them showed promising activities.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► This work reports novel pyrazolotriazines incorporated antipyrine moiety. ► Synthesized compounds were characterized by analytical and spectral data. ► Compounds were screened for their antitumor and antioxidant activities. ► Some of the investigated compounds showed significant activities.