17332-57-9

Usage

Uses

Used in Pharmaceutical Industry:
2,4'-IMINO-DIBENZOIC ACID is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical structure that can be incorporated into drug molecules to enhance their therapeutic properties.
Used in Dye Industry:
In the dye industry, 2,4'-IMINO-DIBENZOIC ACID is utilized as a key component in the production of dyes, capitalizing on its chemical properties to create a range of colorants for different applications.
Used in Polymer Production:
2,4'-IMINO-DIBENZOIC ACID is employed as a monomer in the synthesis of polymers, contributing to the development of materials with specific properties tailored for various uses in industries such as plastics, textiles, and coatings.
Used as an Intermediate in Organic Synthesis:
2,4'-IMINO-DIBENZOIC ACID serves as an intermediate in organic synthesis, facilitating the creation of complex organic compounds through chemical reactions that rely on its reactive functional groups.

Upstream product

• 16463-38-0 potassium 2-chlorobenzoate 
• 150-13-0 4-amino-benzoic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 71-41-0 pentan-1-ol 
• 88-65-3 2-bromobenzoic-acid 
• 88-67-5 2-Iodobenzoic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 134-20-3 2-carbomethoxyaniline 
• 17763-70-1 methyl 2-(trifluoromethylsulfonyloxy)benzoate 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 1415651-26-1 4-acetamidophenyl-2-[{4-{(4-acetamidophenoxy)carbonyl}phenyl}{2-(nitrooxy)ethyl}amino] benzoate 
• 42946-36-1 9-oxo-9,10-dihydro-acridine-2-carboxylic acid 
• 877629-53-3 (4-methyl-piperazin-1-yl)-(9-phenoxy-acridin-2-yl)-methanone 
• 875272-03-0 9-phenoxyacridine-2-carboxylic acid diethylamide 
• 64046-80-6 5-Aminoacridin-3-carbonsaeure 

Relevant academic research and scientific papers

Synthesis, cytotoxicity evaluation, and molecular modeling studies of 2,N10-substituted acridones as DNA-intercalating agents

Acridine-based compounds possess anticancer activities by intercalating to DNA. Although they have chemotherapeutic potential, acridine-based compounds are not used to treat cancer. In this study, 2,N10-acridone derivatives are designed and synthesized based on acridone, a ketone derivative of acridine. Herein, acridone is functionalized with alkyl side chains containing terminal nitrogen-based moieties at the N10-position and substituted at the C2-position. The products are evaluated for in vitro cytotoxicity against four cancer cell lines: Molt-3, HepG2, A549, and HuCCA-1. The derivative bearing two butyl piperidine side chains at the C2- and N10-positions is the most active, with IC50 values ranging from 2.96 to 9.46 μM. Molecular modeling studies supported the binding of the derivatives to DNA by intercalation, thereby confirming the observed cytotoxic effects.

Nitric oxide releasing acridone carboxamide derivatives as reverters of doxorubicin resistance in MCF7/Dx cancer cells

A series of nitric oxide donating acridone derivatives are synthesized and evaluated for in vitro cytotoxic activity against different sensitive and resistant cancer cell lines MCF7/Wt, MCF7/Mr (BCRP overexpression) and MCF7/Dx (P-gp expression). The resu

Bis-substituted diphenylamine arylidene hydrazones for the synthesis of new binuclear organotin(IV) complexes: Crystal structure, DNA cleavage and molecular docking

Five dinuclear organotin(IV) complexes, R4Sn2La (R = Me, Ph) and R4Sn2Lb (R = Me, Ph and Bu) have been synthesized from reaction of R2SnCl2 with 2,4′- and 2,2′-bis-sub

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.

Developing bivalent ligands to target CUG triplet repeats, the causative agent of myotonic dystrophy type 1

An expanded CUG repeat transcript (CUGexp) is the causative agent of myotonic dystrophy type 1 (DM1) by sequestering muscleblind-like 1 protein (MBNL1), a regulator of alternative splicing. On the basis of a ligand (1) that was previously reported to be active in an in vitro assay, we present the synthesis of a small library containing 10 dimeric ligands (4-13) that differ in length, composition, and attachment point of the linking chain. The oligoamino linkers gave a greater gain in affinity for CUG RNA and were more effective when compared to oligoether linkers. The most potent in vitro ligand (9) was shown to be aqueous-soluble and both cell- and nucleus-permeable, displaying almost complete dispersion of MBNL1 ribonuclear foci in a DM1 cell model. Direct evidence for the bioactivity of 9 was observed in its ability to disperse ribonuclear foci in individual live DM1 model cells using time-lapse confocal fluorescence microscopy.

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.

Synthesis and biological evaluation of novel 2,4′-bis substituted diphenylamines as anticancer agents and potential epidermal growth factor receptor tyrosine kinase inhibitors

Four new series of 2,4′-bis diphenylamine hydrazones 14, 2,4′-bis aminothiadiazole 16, 2,4′-bis mercaptotriazole 17-18 and 2,4′-bis mercapto-oxadiazole diphenylamine derivatives 19-20 were synthesized and evaluated for their ability to inhibit EGFR tyrosine kinase. Compound N-ethyl-5-{2-[4-(5-(ethylamino)-1,3,4-thiadiazol-2-yl)- phenylamino]phenyl}-1,3,4-thiadiazol-2-amine 16a was the most active enzyme inhibitor (98% inhibition at 10 μM). Moreover, all compounds that showed enzyme inhibition activity were tested in vitro on human breast carcinoma cell line (MCF-7) in which EGFR is highly expressed. The tested compounds exploited potent antitumor activity with IC50 values ranging 0.73-2.38 μM. Molecular modeling and docking of the synthesized compounds into the active site of EGFR kinase domain showed good agreement with the obtained biological results. The present work represents a novel class of diphenylamine based derivatives with potent cytotoxicity and promising EGFR PTK inhibition activity. Several analogues 2,4′-bis substituted diphenylamines were synthesized and evaluated as EGFR tyrosine kinase inhibitors as well as for their antiprolifertive properties on human breast cancer cell lines (MCF-7).

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%).

A simple and environmentally friendly method for the synthesis of N-phenylanthranilic acid derivatives

A simple, efficient and environmentally friendly method for the synthesis of N-phenylanthranilic acid derivatives by the copper acetate catalysed reaction of o-halobenzoic acid with anilines using sodium acetate as base and water as media is described.

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).