57531-19-8

Basic information

• Product Name: 4-oxo-3-phenyl-phthalazine-1-carboxylic acid
• Synonyms: 4-oxo-3-phenyl-phthalazine-1-carboxylic acid
• CAS NO: 57531-19-8
• Molecular Formula: C₁₅H₁₀N₂O₃
• Molecular Weight: 266.26
• Mol File: 57531-19-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 488.8°Cat760mmHg
• Flash Point: 249.4°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 2.27E-10mmHg at 25°C
• PKA: -3.21±0.20(Predicted)
• CAS DataBase Reference: 4-oxo-3-phenyl-phthalazine-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-oxo-3-phenyl-phthalazine-1-carboxylic acid(57531-19-8)
• EPA Substance Registry System: 4-oxo-3-phenyl-phthalazine-1-carboxylic acid(57531-19-8)

Safety Data

• Hazardous Substances Data: 57531-19-8(Hazardous Substances Data)

Usage

General Description

4-oxo-3-phenyl-phthalazine-1-carboxylic acid is a compound with a chemical formula C13H8N2O4. It belongs to the phthalazine class of compounds and is characterized by a phthalazine ring with a phenyl group and a carboxylic acid functional group. 4-oxo-3-phenyl-phthalazine-1-carboxylic acid has potential applications in medicinal chemistry, particularly in the development of pharmaceuticals and therapeutic agents. Its unique structure and properties make it a valuable building block for the synthesis of various bioactive molecules and potential drug candidates. Additionally, the presence of the carboxylic acid group allows for potential modification and functionalization, making it a versatile and valuable chemical entity in chemical and pharmaceutical research.

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

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

Downstream Products

• 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 
• 40849-07-8 4-oxo-3-phenyl-3,4-dihydro-phthalazine-1-carboxylic acid ethyl ester 
• 6266-49-5 2-phenylphthalazin-1-one 
• 16015-51-3 methyl 4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxylate 

Relevant articles and documents

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.

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.