528-46-1

Usage

Uses

Used in Plastics Industry:
Phthalonic acid is used as a monomer in the production of synthetic resins, which are essential components in the manufacturing of various plastic products.
Used in Pharmaceutical Industry:
Phthalonic acid is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and medications.
Used in Dye Industry:
Phthalonic acid is used as a precursor in the manufacture of pigments, such as phthalein dyes, which are widely used in the textile industry for dyeing and printing applications.
Used in Organic Synthesis:
Phthalonic acid is used as a versatile building block in the synthesis of various organic compounds, enabling the development of new materials with advanced properties.
However, it is important to handle phthalonic acid with care, as it is toxic and can cause skin and eye irritation.

InChI:InChI=1/C9H6O5/c10-7(9(13)14)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,11,12)(H,13,14)

Upstream product

• 577-56-0 2-acetyl-benzoic acid 
• 232-95-1 naphtho[2,1-b]furan 
• 91-20-3 naphthalene 
• 21758-86-1 1,4-dioxo-3-(pyridin-1-ium-1-yl)-1,4-dihydronaphthalen-2-olate 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 119-64-2 tetralin 
• 605-37-8 isonaphthazarine 
• 93-04-9 2-Methoxynaphthalene 
• 25177-85-9 2-indancarboxylic acid 
• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 
• 64-17-5 ethanol 
• 58292-81-2 1,1,3,3-tetrachloro-indan-2-one 
• 524-42-5 1,2-naphthoquinone 
• 95-13-6 1-indene 

Downstream Products

• 791638-32-9 2-[Methoxy(oxo)acetyl]benzoesaeure 
• 85974-70-5 methyl ortho-[(methoxycarbonyl)carbonyl]benzoate 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 119-67-5 o-carboxybenzaldehyde 
• 959362-40-4 2-anilinooxalyl-benzoic acid 
• 29337-71-1 2-phenyliminomethyl-benzoic acid 
• 23146-19-2 2-(3-oxo-3,4-dihydro-quinoxalin-2-yl)-benzoic acid 
• 509-34-2 rhodamine B 
• 57531-19-8 4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxylic acid 
• 89-51-0 Homophthalic acid 
• 90560-48-8 2-carboxy-mandelic acid 
• 106871-71-0 (2-carboxy-phenyl)-imino-acetic acid 
• 144-62-7 oxalic acid 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Exploration of novel phthalazinone derivatives as potential efflux transporter inhibitors for reversing multidrug resistance and improving the oral absorption of paclitaxel

Chemotherapy is an important means of cancer treatment. However, overexpression of efflux transporters (including but not limited to P-gp and BCRP) can lead to resistance to cancer chemotherapy. Multiple-target inhibitors of efflux transporter can be overcome the resistance and improve the oral bioavailability of chemotherapy drugs. Therefore, we designed and synthesized a series of phthalazinone ring derivatives (1-20) with different aromatic heterocycles substituents on the amide bond for dual inhibition of P-gp and BCRP. Most target compounds significantly increased the accumulation of P-gp substrates in the chemo-resistant cancer cell lines by inhibiting the efflux of transporters. Compound 19 in particular showed stronger MDR reversal compared to Gefitinib and Verapamil, and comparable to that of the BCRP inhibitor Ko143. In addition, compound 19 improved intestinal absorption of paclitaxel (PTX) and enhanced the bioavailability of the orally administered drug in vivo.

Synthesis of 2-oxoglutarate derivatives and their evaluation as cosubstrates and inhibitors of human aspartate/asparagine-β-hydroxylase

2-Oxoglutarate (2OG) is involved in biological processes including oxidations catalyzed by 2OG oxygenases for which it is a cosubstrate. Eukaryotic 2OG oxygenases have roles in collagen biosynthesis, lipid metabolism, DNA/RNA modification, transcriptional regulation, and the hypoxic response. Aspartate/asparagine-β-hydroxylase (AspH) is a human 2OG oxygenase catalyzing post-translational hydroxylation of Asp/Asn-residues in epidermal growth factor-like domains (EGFDs) in the endoplasmic reticulum. AspH is of chemical interest, because its Fe(ii) cofactor is complexed by two rather than the typical three residues. AspH is upregulated in hypoxia and is a prognostic marker on the surface of cancer cells. We describe studies on how derivatives of its natural 2OG cosubstrate modulate AspH activity. An efficient synthesis of C3- and/or C4-substituted 2OG derivatives, proceedingviacyanosulfur ylid intermediates, is reported. Mass spectrometry-based AspH assays with >30 2OG derivatives reveal that some efficiently inhibit AspHviacompeting with 2OG as evidenced by crystallographic and solution analyses. Other 2OG derivatives can substitute for 2OG enabling substrate hydroxylation. The results show that subtle changes,e.g.methyl- to ethyl-substitution, can significantly alter the balance between catalysis and inhibition. 3-Methyl-2OG, a natural product present in human nutrition, was the most efficient alternative cosubstrate identified; crystallographic analyses reveal the binding mode of (R)-3-methyl-2OG and other 2OG derivatives to AspH and inform on the balance between turnover and inhibition. The results will enable the use of 2OG derivatives as mechanistic probes for other 2OG utilizing enzymes and suggest 2-oxoacids other than 2OG may be employed by some 2OG oxygenasesin vivo.

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.

α-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases

A series of aryl α-ketocarboxylic acids was synthesized and investigated as inhibitors for the protein tyrosine phosphatase from Yersinia enterocolitica. IC50 values for these compounds range from 79 to 2700 μM. Larger aromatic groups, and aromatic groups with high electron density, lead to more potent inhibitors. In general, the related aryl α-hydroxycarboxylic acids show lower activity.

COBALT CARBONYL-CATALYZED DOUBLE-CARBONYLATION OF O-HALOGENATED BENZOIC ACIDS UNDER PHOTOSTIMULATION

Cobalt carbonyl-catalyzed double-carbonylation of o-dihalobenzenes and o-halogenated benzoic acids, affording phthalonic acid, was observed in aqueous sodium hydroxide under photostimulation.

4-Amino-6-(2-carboxyphenyl)-3-mercapto-1,2,4-triazin-5(4H)-one

4-Amino-6-(2-carboxyphenyl)-3-mercapto-1,2,4-triazin-5(4H)-one is prepared by the reaction of phthalonic acid or its potassium salt with thiocarbohydrazide. The product melts at 180° at which temperature it decarboxylates, resolidifies, and remelts at 235°-240° as the known 6-phenyl derivative. The compound is useful as a selective herbicide.