7221-31-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID is used as an intermediate in the production of active pharmaceutical ingredients. Its unique chemical structure allows it to be a key component in the development of various medications, contributing to their therapeutic properties.
Used in Dye and Pigment Industry:
2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID is utilized as a dye intermediate, playing a crucial role in the creation of various dyes and pigments. Its chemical properties enable it to impart color and stability to a range of products in this industry.
Safety Considerations:
It is important to handle 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID with care, as it can pose health hazards if not properly managed. Adequate safety measures should be taken during its production, storage, and use to minimize potential risks to human health and the environment.

InChI:InChI=1/C13H10N2O4/c16-13(17)11-3-1-2-4-12(11)14-9-5-7-10(8-6-9)15(18)19/h1-8,14H,(H,16,17)

Upstream product

• 100-01-6 4-nitro-aniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 1570135-37-3 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-((4-nitrophenyl)amino)benzamide 
• 17763-70-1 methyl 2-(trifluoromethylsulfonyloxy)benzoate 
• 88-67-5 2-Iodobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 118-92-3 anthranilic acid 
• 586-78-7 para-nitrophenyl bromide 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 7251-00-5 2-nitroacridone 
• 41139-95-1 N-(p-aminophenyl)anthranilic acid 
• 78938-55-3 2-(4-Nitro-phenylamino)-benzoic acid 2-[(E)-2,4-dioxo-imidazolidin-1-ylimino]-ethyl ester 
• 95216-61-8 2-(4-nitrophenylamino)benzamide 
• 95216-44-7 1-(4-aminophenyl)-2-isopropyl-4(1H)-quinazolinone 
• 70368-48-8 2-Isopropyl-1-(4-nitro-phenyl)-1H-quinazolin-4-one 
• 95216-41-4 2-Cyclopropyl-1-(4-nitro-phenyl)-1H-quinazolin-4-one 
• 95216-43-6 2-cyclobutyl-1-(4-nitrophenyl)-4(1H)-quinazolinone 
• 1415651-24-9 4-acetamidophenyl-2-[{2-(nitrooxy)ethyl}(4-nitrophenyl)amino]benzoate 
• 1415651-19-2 C₂₃H₂₀ClN₃O₅ 
• 1415651-14-7 C₂₁H₁₇N₃O₅ 
• 581-28-2 2-aminoacridine 
• 27918-14-5 2-aminoacridone 

Relevant academic research and scientific papers

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

Supramolecular ensemble of PBI derivative and copper nanoparticles: A light harvesting antenna for photocatalytic C(sp2)-H functionalization

Supramolecular aggregates of triazole-appended perylene bisimide (PBI) derivative 3 served as reactors for the generation of copper nanoparticles (CuNPs). During the reduction process, these aggregates were oxidized to triazole N-oxide species 4. Interestingly, the in situ generated CuNPs, in combination with oxidized species 4 (supramolecular ensemble 4:CuNPs), exhibited excellent photocatalytic efficiency in C(sp2)-H alkynylation and amination reactions of arenes under mild and eco-friendly conditions (inexpensive catalyst, room temperature, mixed aqueous media, aerial conditions and visible light irradiation).

Synthesis and characterization of 1-carboxyphenothiazine derivatives bearing nitrogen mustard as promising class of antitubercular agents

A series of 1-carboxyphenothiazines bearing nitrogen mustard was synthesized, characterized, and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv. The results showed that compounds 5h, 5i and 5j found most active with percentage inhibition of 96, 91, and 92, respectively, at minimum inhibitory concentration (MIC) of 6.25 μg/mL. The structures of synthesized compounds were elucidated by various spectroscopic tools like IR, 1H NMR, 13C NMR, mass and elemental analysis. 2013 Bentham Science Publishers.

Synthesis and investigation of anti-inflammatory activity of novel nitric oxide donating hybrid drugs

A small library of nitric oxide donating groups, 4-acetamidophenyl-2-[{2- (nitrooxy)ethyl}(phenyl) amino]benzoate (5a-e) possessing a variety of substituents (-H, -NO2, -CH3, -acetamidophenyl, -SO 2NH2) attached to the fourth position of phenyl ring were synthesized and evaluated for anti-inflammatory, analgesic and ulcerogenic potential. Structure-activity relationship data showed that the 2-phenylaminobenzoic acid skeleton is required for selective COX-2 inhibition. Among all compounds 4-acetamidophenyl-2-[{2-(nitrooxy)ethyl}(phenyl)amino] benzoate (5a) has shown potent anti-inflammatory activity while 4-acetamidophenyl-2-[{4-{(4-acetamidophenoxy)carbonyl} phenyl}{2-(nitrooxy) ethyl}amino]benzoate (5d) has shown potent analgesic activity compared to standard drug diclofenac.

Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships

Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.

NOVEL ANTHRANILIC ACID DERIVATIVES AND CHLORIDE CHANNEL BLOCKING AGENT CONTAINING THE SAME

The present invention relates to novel anthranilic acid derivatives represented by Chemical Formula I, and a chloride channel blocking agent containing the anthranilic acid derivative or its pharmacologically acceptable salts as an active ingredient. In another aspect, the present invention relates to a method of accurately and efficiently detecting the intracellular chloride channel inhibition and method of screening a chloride channel blocking agent.

Regioselective copper-catalysed amination of halobenzoic acids using aromatic amines

Copper dipyridine dichloride (CuPy2Cl2) has been found to be an efficient catalyst for the synthesis of N-arylanthranilic acids from ortho halobenzoic acids and aromatic amines under microwave irradiation. Some of the advantages of this method are high chemoselectivity, ease of operation, less reaction times and high yields. (61-98%).

Regioselective copper-catalyzed amination of chlorobenzoic acids: Synthesis and solid-state structures of N-aryl anthranilic acid derivatives

A chemo- and regioselective copper-catalyzed cross-coupling reaction for effective amination of 2-chlorobenzoic acids with aniline derivatives has been developed. The method eliminates the need for acid protection and produces a wide range of N-aryl anthranilic acid derivatives in up to 99% yield. The amination was found to proceed with both electron-rich and electron-deficient aryl chlorides and anilines and also utilizes sterically hindered anilines such as 2,6-dimethylaniline and 2-tert-butylaniline. The conformational isomerism of appropriately substituted N-aryl anthranilic acids has been investigated in the solid state. Crystallographic analysis of seven anthranilic acid derivatives showed formation of two distinct supramolecular architectures exhibiting trans-anti and unprecedented trans-syn dimeric structures.

Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines

A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).

Use of amino-substituted benzoic acids as remedies for diarrhea, and medicaments based on these compounds

A description is given of the use of amino-substituted benzoic acid derivatives of the formula I STR1 in which R1 and R2 denote hydrogen, (cyclo)alkyl, unsubstituted or substituted phenyl or naphthyl, or R1 and R2 together denote a chain --(CH2)m -- with m=3 to 6, or together denote a chain --(CH=CH)n -- with n equal to 2 or 3; R3 denotes hydrogen, halogen or alkyl; R4 denotes hydrogen or NO2 ; R5 denotes hydrogen or a radical which can be eliminated under physiological conditions; for the preparation of a remedy for diarrhea.