1239164-95-4

Basic information

• Product Name: 2-oxo-1-phenyl-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• Synonyms: 2-oxo-1-phenyl-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• CAS NO: 1239164-95-4
• Molecular Weight: 294.31
• Mol File: 1239164-95-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-oxo-1-phenyl-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxo-1-phenyl-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester(1239164-95-4)
• EPA Substance Registry System: 2-oxo-1-phenyl-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester(1239164-95-4)

Safety Data

• Hazardous Substances Data: 1239164-95-4(Hazardous Substances Data)

Upstream product

• 21093-54-9 2-Phenylamino-3-hydroxymethylpyridine 
• 16344-24-4 2-(phenylamino)nicotinic acid 
• 2942-59-8 2-chloronicotinic acid 
• 62-53-3 aniline 
• 113256-66-9 2-phenylamino-3-pyridinecarboxaldehyde 
• 105-53-3 diethyl malonate 

Downstream Products

• 1239164-92-1 2-oxo-1-phenyl-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid 
• 1239164-66-9 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid chloride 
• 1239164-22-7 3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1-phenyl-1,8-naphthyridin-2(1H)-one 
• 1239164-65-8 3-oxo-1-cyclohexenyl 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylate 

Relevant articles and documents

Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 1,8-naphthyridin-2-one moiety

A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 1,8-naphthyridin-2-one moiety were designed, synthesized and evaluated for their biological activities. The target compounds exhibited moderate to high antiproliferative activity against three cancer cell lines (A549, HepG2 and MCF-7) and several compounds (25, 27, 33, 37, 41, 43, 49 and 53) were evaluated for the activity against c-Met kinase. The most promising compound 33 (IC50 c-Met = 2.36 nM) showed excellent activity against A549, HepG2 and MCF-7 cell lines with IC50 values of 0.23 μM, 0.42 μM and 0.21 μM, respectively, which was 1.5–2.1 times of the positive control. Furthermore, compound 33 was evaluated for the activity against Flt3, PDGFR-α PDGFR-β c-Kit, Flt4, ALK and EGFR kinase. Structure activity relationship studies indicated that mono-EWGs (such as R2 = F) at 4-position of moiety C was a key factor in improving the antitumor activity. In addition, further research on compound 33 was mainly including concentration dependence, apoptosis (acridine orange staining), apoptosis result analyzing and molecular docking.

Synthesis and antiproliferative activity of pyrrolo[2,3-b]pyridine derivatives bearing the 1,8-naphthyridin-2-one moiety

A series of pyrrolo[2,3-b]pyridine derivatives bearing the 1,8-naphthyridin-2-one moiety were synthesized, and evaluated for their antiproliferative activity against four cancer cell lines (HT-29, A549, H460, and U87MG) and six tyrosine kinases (c-Met, Flt-3, PDGFR-β VEGFR-2, EGFR, and c-Kit) inhibitory activities in vitro. Most compounds showed moderate to excellent potency, with the most promising analogue 32 showing Flt-3/c-Met IC50 value of 1.16/1.92 nM. Structure-activity relationship studies indicated that the hydrogen atom served as R1 group was benefited to the potency, and mono-electron-withdrawing groups (mono-EWGs) on the phenyl ring (such as R3 = 4-F) showed a higher preference for antiproliferative activity.

Preparation and application of 2-carbamoyl-4-heteroaromatic pyridine compounds

The invention provides 2-carbamoyl-4-heteroaromatic pyridine derivatives and pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof. The substituent groups R1, R2 and Y have definitions in the specification. The invention further relates to compounds with a general formula I having strong effects of inhibiting c-Met kinase, and also relates to an application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of medicines for treating diseases caused by abnormal high expression of the c-Met kinase, particularly an application in preparation of medicines for treating and/or preventing cancers.