57531-19-8

Usage

Uses

Used in Pharmaceutical Industry:
4-oxo-3-phenyl-phthalazine-1-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals and therapeutic agents. Its unique structure and properties contribute to the development of new drugs with potential applications in various therapeutic areas.
Used in Medicinal Chemistry Research:
As a versatile chemical entity, 4-oxo-3-phenyl-phthalazine-1-carboxylic acid is used in medicinal chemistry research for the exploration of its potential as a bioactive molecule. The presence of the carboxylic acid group allows for further modification and functionalization, enabling the creation of novel drug candidates with improved pharmacological properties.
Used in Chemical Research:
4-oxo-3-phenyl-phthalazine-1-carboxylic acid is also utilized in chemical research to study its reactivity and potential applications in the synthesis of other organic compounds. Its unique structure and properties make it an interesting subject for investigation in various chemical reactions and processes.

InChI:InChI=1/C15H10N2O3/c18-14-12-9-5-4-8-11(12)13(15(19)20)16-17(14)10-6-2-1-3-7-10/h1-9H,(H,19,20)/p-1

Upstream product

• 91-20-3 naphthalene 
• 528-46-1 phthalonic acid 
• 59-88-1 phenylhydrazine hydrochloride 
• 7732-18-5 water 
• 100-63-0 phenylhydrazine 
• 7647-01-0 hydrogenchloride 
• 62-53-3 aniline 
• 16015-51-3 methyl 4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxylate 
• 791638-32-9 2-[Methoxy(oxo)acetyl]benzoesaeure 
• 90-15-3 α-naphthol 

Downstream Products

• 40849-07-8 4-oxo-3-phenyl-3,4-dihydro-phthalazine-1-carboxylic acid ethyl ester 
• 1616244-75-7 N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxamide 
• 1616244-69-9 N-(3-fluoro-4-((6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxamide 
• 1616244-62-2 N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxamide 
• 1616244-54-2 N-(3-fluoro-4-((6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxamide 
• 1616244-47-3 N-(3-fluoro-4-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)phenyl)-4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxamide 
• 40849-11-4 4-hydroxymethyl-2-phenyl-2H-phthalazin-1-one 
• 6266-49-5 2-phenylphthalazin-1-one 
• 16015-51-3 methyl 4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxylate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of N-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-4-oxo-3,4-dihydrophthalazine-1-carboxamide derivatives as novel P-glycoprotein inhibitors reversing multidrug resistance

The overexpression of P-glycoprotein plays an important role in the process of multidrug resistance (MDR). P-gp inhibitors are one of the effective strategies to reverse tumor MDR. Novel P-gp inhibitors with phthalazinone scaffolds were designed, synthesized and evaluated. Compound 26 was found to be the most promising for further study. Compound 26 possessed high potency (EC50 = 46.2 ± 3.5 nM) and low cytotoxicity.26 possessed high MDR reversal activity towards doxorubicin-resistant K56/A02 cells. Reversal fold (RF) value reach to 44.26. 26 also increased accumulation of doxorubicin (DOX or ADM) or other MDR-related anticancer drugs with different structures. In conclusion, compound 26 deserves more research for its good features as P-gp inhibitor.

Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors

Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.

Design, synthesis and biological evaluation of novel 6,7-disubstituted-4- phenoxyquinoline derivatives bearing 4-oxo-3,4-dihydrophthalazine-1-carboxamide moieties as c-Met kinase inhibitors

A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 4-oxo-3,4-dihydrophthalazine-1-carboxamide moieties were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against H460, MKN-45, HT-29 and MDA-MB-231 cancer cell lines in vitro. Most compounds displayed good to excellent potency against four tested cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially fluoro groups at 4-position on the phenyl ring (moiety B) were more effective than those with nitro groups or methoxy groups. In this study, a promising compound 33 (c-Met IC50 = 1.63 nM) was identified, which showed the most potent antitumor activities with IC50 values of 0.055 μM, 0.071 μM, 0.13 μM, and 0.43 μM against H460, MKN-45, HT-29 and MDA-MB-231 cell lines, respectively.

Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin- 4(5H)-one and 4-aminophthalazin-1(2H)-ones

We hereby report the synthesis of a novel class of compounds, 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones starting from methyl 2-(2-methoxy-2-oxoethyl)furan- and thiophene-3-carboxylate and methyl 2-(2-methoxy