72396-65-7Relevant academic research and scientific papers
Synthesis and evaluation of new 4-Chloro-2-(3-chloro-4-fluorophenyl)-5-(aliphatic/cyclic saturated amino)pyridazin-3(2H)-one derivatives as anticancer, antiangiogenic, and antioxidant agents
Kamble, Vinod T.,Sawant, Ajay S.,Sawant, Sanjay S.,Pisal, Parshuram M.,Gacche, Rajesh N.,Kamble, Sonali S.,Kamble, Vilas A.
, p. 338 - 346 (2015)
Pyridazinones are widely recognized as versatile scaffolds with a wide spectrum of biological activities. In the present work, a series of new 4-chloro-2-(3-chloro-4-fluorophenyl)-5-(aliphatic/cyclic saturated amino)pyridazin-3(2H)-one derivatives 4a-i were synthesized and characterized by spectral techniques. The inhibitory effects of the synthesized compounds 4a-i on the viability of three human cancer cell lines, HEP3BPN 11 (liver), MDA 453 (breast), and HL 60 (leukemia), were assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction assay. Among the compounds 4a-i screened, 4g and 4i exhibited inhibitory activity very close to the standard methotrexate; therefore, these lead compounds were further tested for their potential to inhibit the proangiogenic cytokines involved in tumor progression. Compound 4g was found to be a potent antiangiogenic agent against TNFα, VEGF, FGFb, and TGFβ, whereas 4i showed potent antiangiogenic activity against TNFα, VEGF, FGFb, and leptin. All the compounds 4a-i were screened for their antioxidant activities using 2,2-diphenyl-1-picryl hydrazine (DPPH), OH, and superoxide anion radicals. Compound 4f showed better OH radical scavenging activity than the standard ascorbic acid. A series of new 4-chloro-2-(3-chloro-4-fluorophenyl)-5-(aliphatic/cyclic saturated amino)pyridazin-3(2H)-one derivatives (4a-i) were assessed for their anticancer potential by measuring their MTT-based cytotoxicity against selected cancer cell lines. The promising leads (4g and 4i) were further tested for their potential to inhibit the proangiogenic cytokines involved in tumor progression.
Confirmation and prevention of halogen exchange: practical and highly efficient one-pot synthesis of dibromo- and dichloropyridazinones
Zhang, Ji,Morton, Howard E.,Ji, Jianguo
, p. 8733 - 8735 (2007/10/03)
Commercially available anilines were converted by a two step, one-pot process to the corresponding pyridazinones in good to excellent yields. During the process research, a significant halogen exchange was confirmed and prevented which allowed the process to be scaled to multikilogram quantities.
