title: Synthesis, antitumor, cytotoxic and antioxidant evaluation of some new pyrazolotriazines attached to antipyrine moiety.
abstract: 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).
authors.affiliation: Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt. mamegs@mans.edu.eg
authors.forename: M A
authors.initials: MA
authors.lastname: Metwally
authors.forename: M A
authors.initials: MA
authors.lastname: Gouda
authors.forename: Ammar N
authors.initials: AN
authors.lastname: Harmal
authors.forename: A M
authors.initials: AM
authors.lastname: Khalil
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000983:Antipyrine / Q000737:chemistry*; D001761:Bleomycin / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D004249:DNA Damage; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D056945:Hep G2 Cells; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014709:Vero Cells
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D011720:Pyrazoles; D001761:Bleomycin; D000983:Antipyrine