title: Synthesis and antitumor activities of some new N1-(flavon-6-yl)amidrazone derivatives.
abstract: A new series of N1-(flavon-6-yl)amidrazones were synthesized by reacting the hydrazonoyl chloride derived from 6-aminoflavone with the appropriate sec-cyclic amines. The antitumor activities of these compounds were evaluated on breast cancer (MCF-7) and leukemic (K562) cell lines. Among the compounds tested, the N-morpholine derivative was the most active against the MCF-7 and K562 cell lines, with IC50 values of 5.18 and 2.89 μM, respectively. Our docking studies showed that the N-morpholino derivative fits and blocks the oncogenic tyrosine kinases bcr/abl and epidermal growth factor receptor (EGFR) in a similar fashion to that of the potent anticancer agent imatinib.
authors.affiliation: Faculty of Science, Chemistry Department, The University of Jordan, Amman, Jordan.
authors.forename: Almeqdad Y
authors.initials: AY
authors.lastname: Habashneh
authors.forename: Mustafa M
authors.initials: MM
authors.lastname: El-Abadelah
authors.forename: Malek A
authors.initials: MA
authors.lastname: Zihlif
authors.forename: Amer
authors.initials: A
authors.lastname: Imraish
authors.forename: Mutasem O
authors.initials: MO
authors.lastname: Taha
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D015195:Drug Design; D066246:ErbB Receptors / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D047309:Flavones / Q000138:chemical synthesis* / Q000494:pharmacology*; D016044:Fusion Proteins, bcr-abl / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D000068877:Imatinib Mesylate; D020128:Inhibitory Concentration 50; D020014:K562 Cells; D061986:MCF-7 Cells; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D010879:Piperazines / Q000494:pharmacology; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D011743:Pyrimidines / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001549:Benzamides; D047309:Flavones; D010879:Piperazines; D047428:Protein Kinase Inhibitors; D011743:Pyrimidines; D000068877:Imatinib Mesylate; C512478:EGFR protein, human; D066246:ErbB Receptors; D016044:Fusion Proteins, bcr-abl
keywords: 4-Oxo-N-(chromen-6-yl)hydrazonoyl chloride; Antitumor activity; N1-(Flavon-6-yl)amidrazones; Oncogenic tyrosine kinases bcr/abl