100124-51-4

Upstream product

• 109019-19-4 4-(4-chloro-phenylhydrazono)-3-methyl-pentenedioic acid-anhydride 
• 100375-28-8 1-(4-chloro-phenyl)-4-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester 
• 109566-81-6 4-methyl-1-phenyl-pyridine-2,3,6-trione-3-(4-chloro-phenylhydrazone) 
• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 1620683-64-8 ethyl 1-(4-chlorophenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate 
• 18794-97-3 ethyl 2-(4-chlorophenylhydrazono)-3-oxobutyrate 
• 106-47-8 4-chloro-aniline 
• 31643-64-8 6-Hydroxy-4-methyl-1-phenyl-1H-pyridin-2-one 

Downstream Products

• 101606-51-3 1-(4-chloro-phenyl)-4-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid anilide 
• 1620683-87-5 1-(4-chlorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide 
• 1620683-95-5 1-(4-chlorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide 
• 1620684-03-8 1-(4-chlorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide 
• 1620684-11-8 1-(4-chlorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide 
• 1633819-06-3 C₁₂H₈Cl₂N₂O₂ 
• 1620683-79-5 1-(4-chlorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)phenyl)-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel N-[4-(2-fluorophenoxy)pyridin-2-yl]cyclopropanecarboxamide derivatives as potential c-Met kinase inhibitors

Three series of novel 4-phenoxypyridine derivatives containing 4-methyl-6-oxo-1,6-dihydropyridazine- 3-carboxamide, 5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide and 4-methyl-3,5-dioxo-2,3,4,5- tetrahydro-1,2,4-triazine-6-carboxamide moieties were synthesized and evaluated for their in vitro inhibitory activitives against c-Met kinase and cytotoxic activitives against A549, H460, HT-29 cancer cell lines. The results indicated that most of the compounds showed moderate to good antitumor activitives. The most promising compound 26a (with c-Met IC50 value of 0.016 μM) showed remarkable cytotoxicity against A549, H460, and HT-29 cell lines with IC50 values of 1.59 μM, 0.72 μM and 0.56 μM, respectively. Their preliminary structure-activity relationships (SARs) studies indicate that 4-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxamide was more preferred as linker part, and electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activitives. Furthermore, the colony formation, acridine orange/ethidium bromide (AO/EB) staining, apoptosis, and wound-healing assay of 26a were performed on HT-29 and/or A549 cell lines.

Design, synthesis and structure-activity relationships of novel 4-phenoxyquinoline derivatives containing pyridazinone moiety as potential antitumor agents

A series of novel 4-phenoxyquinoline derivatives containing pyridazinone moiety were synthesized and evaluated for their in vitro cytotoxic activity against five cancer cell lines (HT-29, H460, A549, MKN-45, and U87MG). Most of the compounds exhibited moderate-to-significant cytotoxicity and high selectivity against one or more cell lines. Compounds 15a, 20a, 15b, 15c, 20d, and 16e were further examined for their inhibitory activity against c-Met kinase. The most promising compound 15a (c-Met half-maximal inhibitory concentration [IC50] = 2.15 nM) showed remarkable cytotoxicity against HT-29, H460, and A549 cell lines with IC50 values of 0.10 μM, 0.13 μM, and 0.05 μM, respectively, and thus it was 1.5- to 2.3-fold more potent than foretinib. Their preliminary structure-activity relationships (SARs) studies indicate that electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activity.