19368-08-2

Basic information

• Product Name: 2''-CARBOXY-PHTHALANIC ACID
• Synonyms: 2''-CARBOXY-PHTHALANIC ACID;2-[(2-Carboxybenzoyl)amino]benzoic acid
• CAS NO: 19368-08-2
• Molecular Formula: C₁₅H₁₁NO₅
• Molecular Weight: 285.254
• Mol File: 19368-08-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2''-CARBOXY-PHTHALANIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2''-CARBOXY-PHTHALANIC ACID(19368-08-2)
• EPA Substance Registry System: 2''-CARBOXY-PHTHALANIC ACID(19368-08-2)

Safety Data

• Hazardous Substances Data: 19368-08-2(Hazardous Substances Data)

Upstream product

• 41513-78-4 2-phthalimidobenzoic acid 
• 88-95-9 Phthaloyl dichloride 
• 118-92-3 anthranilic acid 
• 85-44-9 phthalic anhydride 
• 19795-35-8 2-(oxo-4H-benzo[d][1,3]oxazin-2-yl)-benzoic acid 
• 5766-76-7 2-benzylideneamino-benzoic acid 

Downstream Products

• 41513-78-4 2-phthalimidobenzoic acid 
• 118-92-3 anthranilic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant articles and documents

Inhibitory and Cooperative Effects Regulated by pH in Host-Guest Complexation between Cationic Pillar[5]arene and Reactive 2-Carboxyphthalanilic Acid

The study of host-guest complexation between reactive 2-carboxyphthalanilic acid (CPA) and two cationic pillararenes has been carried out. Host-guest complexation with significant kinetic effects was observed only with the smaller cavity size pillararene (P5A). Kinetics in the pH range 1.50-6.40, ESI-MS, 1H NMR titration, and ROESY experiments were performed to characterize the complexes. High binding stoichiometry (H:G2) was observed for all CPA protonation states. The system is pH-dependent, and inversion of cooperativity (negative to positive) occurs by increasing the dianionic CPA2- concentration (allosteric behavior). Toward physiological pH, association constant K1:1 does not change (104 M-1), and K1:2 increased from 102 to 104 M-1, as well as the inhibitory effect increased up to 222-fold. NMR results elucidated the structure of the complex and allowed us to create a map of H-H interactions that describes well the diversity and number of interactions in the complex. ?

Regiospecific Isomerization of 2-Benzoxazinon-2-yl Benzoic Acid Toward Some Nitrogen Nucleophiles as Environmental Insecticide

Based on the strategies of receptor structure-guided benzoxazinone design, a series of nitrogen nucleophiles such as benzyl amine, sodium azide, 4,4-bis o-toluidine, 4-butanolamine, glucosamine, 2-amino pyridine, 2-picolinyl amine, hydroxyl amine, and hydrazine derivatives, for example, hydrazine hydrate, semicarbazide, thiosemicarbazide, methylhydrazide, phenylhydrazide, could be reacted with 2-benzoxazine-2-yl benzoic acid 1. According the basicity of nucleophiles, regiospecific isomerization of benzoxazinone has been considered through formation of the spiro derivatives. Organic reagents can be controlled on the course of reaction of benzoxazinonyl benzoic acid 1. Preliminary bioassays indicated that the insecticidal spectra of the synthesized compounds were ecofriendly biodegradable materials due to isomerization. Among these analogues, the quinazoline 2–4 showed 100% mortality against Nilaparvata lugens (LC50?=?0.087?mg/L). The insecticidal potency of our designed analogues was dual-controlled by isomerization to quinazolinone and spiro derivatives that observed in vitro and shed light on the novel insecticidal mechanism. The chemical structure of the products can be confirmed by microanalytical, spectral data, optimized and stimulated by quantum chemical parameters.

Design, synthesis and anticancer activities evaluation of novel 5H-dibenzo[b,e]azepine-6,11-dione derivatives containing 1,3,4-oxadiazole units

Rucaparib and PJ34 were used as the structural model for the design of novel 5H-dibenzo[b,e]azepine-6,11-dione derivatives containing 1,3,4-oxadiazole units. And target compounds were successfully synthesized through a 3-step synthetic strategy. All target compounds were screened for their anti-proliferative effects against OVCAR-3 cell line. Preliminary biological study of these compounds provided potent compounds d21 and d22 with better activities than Rucaparib.

Coordination among Bond Formation/Cleavage in a Bifunctional-Catalyzed Fast Amide Hydrolysis: Evidence for an Optimized Intramolecular N-Protonation Event

A density functional theory (DFT) computational analysis, using the ωB97X-D functional, of a rapid amide cleavage in 2-carboxyphthalanilic acid (2CPA), where the amide group is flanked by two catalytic carboxyls, reveals key mechanistic information: (a) General base catalysis by a carboxylate coupled to general acid catalysis by a carboxyl is not operative. (b) Nucleophilic attack by a carboxylate on the amide carbonyl coupled to general acid catalysis at the amide oxygen can also be ruled out. (c) A mechanistic pathway that remains viable involves general acid proton delivery to the amide nitrogen by a carboxyl, while the other carboxylate engages in nucleophilic attack upon the amide carbonyl; a substantially unchanged amide carbonyl in the transition state; two concurrent bond-forming events; and a spatiotemporal-base rate acceleration. This mechanism is supported by molecular dynamic simulations which confirm a persistent key intramolecular hydrogen bonding. These theoretical conclusions, although not easily verified by experiment, are consistent with a bell-shaped pH/rate profile but are at odds with hydrolysis mechanisms in the classic literature.

Compounds and methods for inducing chondrogenesis

The present invention provides compounds and compositions for the amelioration of arthritis and joint injuries by inducing mesenchymal stem cells into chondrocytes.

Dibenzo-azepine-dione anti-tumor compounds and preparation method thereof

The invention provides dibenzo-azepine-dione anti-tumor compounds and a preparation method thereof, belongs to the technical field of medicines and particularly relates to compounds with specific chemical structures with anti-tumor activity. General formulae of the compounds include a general formula I, a general formula II, a general formula III and a general formula IV. The invention further provides an application of the compounds in anti-tumor and the preparation method. Tests of various tumor cell lines such as human lung cancer cells and human gastric carcinoma cells prove that the compounds have the tumor activity inhibition effect. The raw materials of the compounds are easily available, the preparation method is simple, and experiments prove that the compounds have good anti-cancer effect and have good application prospect in the field of design, research and development of anti-tumor drugs.

COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS

Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.

Products from dehydration of dicarboxylic acids derived from anthranilic acid

Treatment of N-(carboxymethyl)-anthranilic acids 1 with several dehydrating agents, gave the cyclic ortho amides 6, or the 7-membered anhydrides 7. After reaction of N-(carboxymethyl)-anthranilic acid (1a) with acetic anhydride, a diacetylated fused diketopiperazine indole dimer (18) could be isolated. Dehydrations of 2,2′-iminobis-benzoic acid led to the corresponding cyclic ortho amides 23. The dynamic behaviour of some of these compounds, and their precursors, was studied.

REACTIONS OF CYCLIC ANHYDRIDES XVI. A NOVEL APPROACH TO ANGULAR OXYGENATED PYRROLOBENZOXAZINONES

o-Carboxymaleanilic acids IIIa-g when treated with sodium acetate-acetic anhydride underwent double cyclisation leading to pyrrolobenzoxazinones Va-g carrying an angular acetate.A one-flask reaction of dimethylmaleic anhydride and phthalic anhydride with anthranilic acid furnished the angular hydroxy benzoxazinones IVh and IVi respectively, which were converted to the corresponding acetates Vh and Vi.The acetates Va, Vc, Vf, Vg and Vi underwent solvolysis to the corresponding methyl ethers (VII) on refluxing with anhydrous methanol.