89-52-1

Usage

Uses

Used in Pharmaceutical Industry:
N-Acetylanthranilic acid is used as an intermediate in the synthesis of various pharmaceutical compounds, including antibiotics, anti-inflammatory drugs, and antidepressants. Its unique chemical structure allows it to be a versatile building block for the development of new drugs.
Used in Chemical Research:
N-Acetylanthranilic acid is used as a research compound in various chemical studies, particularly in the field of organic chemistry. It can be used to investigate the properties and reactions of amidobenzoic acids and their derivatives.
Used in Cosmetic Industry:
N-Acetylanthranilic acid can be used as an active ingredient in cosmetic products, such as creams and lotions, due to its potential skin conditioning and moisturizing properties. It may also have potential applications in hair care products.
Used in Food Industry:
N-Acetylanthranilic acid may have potential applications in the food industry as a flavoring agent or as a component in the synthesis of food additives. Its unique chemical properties could contribute to the development of new flavors or enhance existing ones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4614, 1981 DOI: 10.1021/jo00335a075Tetrahedron Letters, 23, p. 4473, 1982 DOI: 10.1016/S0040-4039(00)85631-2

Purification Methods

Wash the acid with distilled H2O and recrystallise it from aqueous AcOH, dry it and recrystallise again from EtOAc. Also recrystallise it from water or EtOH. UV: max 221, 252 and 305nm (EtOH). The amide crystallises from aqueous EtOH and has m 186-187o and max 218, 252 and 301nm. [Chattaway J Chem Soc 2495 1931, Walker J Am Chem Soc 77 6698 1955, Beilstein 14 H 337, 14 I 540, 14 II 219, 14 III 922.]

InChI:InChI=1/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)/p-1

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 91-63-4 2-methylquinoline 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 118-48-9 isatoic anhydride 
• 108-24-7 acetic anhydride 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 271-58-9 anthranil 
• 14676-43-8 N-dichloroacetyl-anthranilic acid 
• 127-08-2 potassium acetate 
• 871878-63-6 2-(acetyl-hydroxy-amino)-benzaldehyde 
• 859333-44-1 N,N'-(2,2,2-trichloro-ethylidene)-di-anthranilic acid 
• 118-92-3 anthranilic acid 
• 71-43-2 benzene 
• 127-09-3 sodium acetate 

Downstream Products

• 30507-16-5 3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one 
• 1232-38-8 4-(2-methyl-4-oxo-3,4-dihydroquinazolin-3-yl)benzenesulfonamide 
• 2385-23-1 2-Methyl-3-phenyl-4(3H)-quinazolinone 
• 340-57-8 mecloqualone 
• 1221-79-0 2-methyl-3-(phenylamino)quinazolin-4(3H)-one 
• 1897-96-7 3-(4-ethoxyphenyl)-2-methylquinazolin-4(3H)-one 
• 2006-80-6 2-(2-methyl-4-oxo-4H-quinazoline-3-yl)benzoic acid methyl ester 
• 93432-37-2 3-(2-chloro-4-nitro-phenyl)-2-methyl-3H-quinazolin-4-one 
• 72-44-6 methaqualone 
• 4260-34-8 3-benzyl-2-methyl-3H-quinazolin-4-one 
• 134-20-3 2-carbomethoxyaniline 
• 56982-16-2 3-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid methyl ester 
• 100951-30-2 N-acetyl-anthranilic acid-{2-[bis-(2-chloro-ethyl)-amino]-ethyl ester} 
• 32002-03-2 bis-[4-(2-acetylamino-benzoyloxy)-phenyl]-sulfone 

Relevant academic research and scientific papers

Acylanthranils. 10. Influence of Hydrogen Bonding on Hydrolysis of Acetylanthranil in Organic Solvents

The hydrolysis of acetylanthranil (1) to give o-acetamidobenzoic acid (2) in organic solvents at room temperature was monitored by proton NMR and/or gravimetrically.The results show that the second-order rate constant in benzene is about equal to that in water at pH 6.8.The corresponding rate constant for hydrolysis by a stoichiometric amount of water in proton-acceptor solvents decreases in the order benzene > dimethyl-d6 sulfoxide > acetone-d6 > dimethylformamide-d7 > pyridine, and for hydrolysis in proton donor solvents, it decreases in the order benzene > chloroform-d > acetonitrile-d3.The observed second-order rate "constant" in organic solvents, however, is not a true constant, since it increases linearly with water concentration.It was observed also that the plots of log / as a function of time, t, show an inflection at some time, ti, that appears to correspond to a critical equilibrium concentration of available proton from the acid product 2.The magnitude of ti is decreased considerably by addition of 2 at time zero, and it is eliminated completely by addition of HCl.On the other hand, it is increased considerably by addition of solutes that are strong proton acceptors, such as 1,8-bis(dimethylamino)naphthalene or 1,4-diazabicyclooctane.These results are consistent with the hypothesis that hydrolysis of 1 in organic solvents involves interaction with molecular clusters of water such as (H2O)n in benzene, S*HOH*S or (HOH*S)n in proton-acceptor solvents, S, and H2O*HS in proton donor solvents, SH.

N-Acetylanthranilic Acid (o-Acetamidobenzoic Acid), a Strongly Triboluminescent Material

C9H9NO3, orthorombic, Fdd2, a = 10.845 (9), b = 30.204 (7), c = 10.575 (4) Angstroem, V = 3464 Angstroem3, Dx = 1.378, Dm = 1.36 Mg m-3 (by flotation), Z = 16.The final R = 0.064 for 799 reflexions and 118 variables.The molecules are interbonded by hydrogen bonds throught the O(1) of the carboxyl group and O(31) of the acetamide group forming chains on alternating planes approximately parallel to (301) and .

Synthesis and X-ray structure analysis of 2-acetylamino-benzoic acid

The title compound crystallizes in the orthorhombic space group Fdd2 with unit cell parameters a = 10.848(1) , b = 30.264(1) and c = 10.577(1) , V = 3472.47(2) 3, and Z = 4. The final reliability index is 0.030 for 700 observed reflections. Nitrogen of the amide group and carbon atom of the acid group deviate significantly below and above the plane of the phenyl ring. The crystal cohesion is accentuated by NbondHO and ObondHO hydrogen bonds.

Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents

The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger-scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. (Figure presented.).

Cleavage of Carboxylic Esters by Aluminum and Iodine

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

MODIFIED PROTEINS AND PROTEIN DEGRADERS

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

Design and synthesis of novel tranilast analogs: Docking, antiproliferative evaluation and in-silico screening of TGFβR1 inhibitors

The discovery of the antiproliferative potential of tranilast prompted additional studies directed at understanding the mechanisms of tranilast action. Its inhibitory effect on cell proliferation depends principally on the capacity of tranilast to interfere with transforming growth factor beta (TGFβR1) signaling. This work summarizes design, synthesis and biological evaluation of sixteen novel tranilast analogs on different tumors such as PC-3, HepG-2 and MCF-7 cell lines. The in vitro cytotoxicity was evaluated using MTT assay showed that, twelve compounds out of sixteen showed higher cytotoxic activities (IC50’s 1.1–6.29 μM), than that of the reference standard, 5-FU (IC50 7.53 μM). The promising cytotoxic hits (4b, 7a, b and 14c-e), proved to be selective to cancer cells when their cytotoxicity's are examined on human normal cell line (WI-38). Then they are investigated for their possible mode of action as TGFβR1 inhibitors; remarkable inhibition of TGFβR1 by these hits was observed at the range of IC50 0.087–3.276 μM. The cell cycle analysis of the most potent TGFβR1 inhibitor, 4b revealed cell cycle arrest at G2/M phase on prostate cancer cells. Additionally, it is clearly indicated apoptosis induction at Pre-G1 phase, this is substantiated by significant increase in the expression on the tumor suppressor gene, p53 and up regulation the level of apoptosis mediator, caspase-3. In addition, in silico study was performed for validating the physicochemical and ADME properties which revealed that, all compounds are orally bioavailable with no side effects complying with Lipinski rule. The proposed mode of action can be further explored on the light of molecular modeling simulation of the most potent compounds, 4b and 14e which were docked into the active sites of TGFβR1 to predict their affinities toward the receptor.

Preparation method of dye intermediate applicable to digital jet printing or dyeing

The invention relates to a preparation method of a dye intermediate applicable to digital jet printing or dyeing. The active dye intermediate is 2-carboxyl-4-beta sulfonylsulfone ethyl sulfate-aniline. The method comprises the following steps of (1) acetylation; (2) sulfochlorination; (3) reduction; (4) hydroxyethylation; (5) esterification hydrolysis. The dye intermediate prepared by the method is applicable to synthesis of digital jet printing or dyeing.

A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity

A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert-butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a-s) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL-1) and compounds 2d and 2p showed the maximum (32 μg mL-1) antifungal activity against A. flavus and C. albicans.

A photochemical approach for evaluating the reactivity of substituted lappaconitines

Lappaconitine (LC) is a natural diterpenoid alkaloid (DTA), acting as a human heart sodium channel blocker and possessing a wide range of biological activities, the cellular and molecular mechanisms of which are widely studied. This interest is due to the fact that various representatives of this DTA class show opposite biological activities. The possible reasons for this difference seem to be related to the peculiarities of the substituent effect on the drug-receptor binding process. In this work, the influence of substituents on the reactivity of LC and its derivatives has been studied by using elementary processes of photodecomposition. The given approach includes the joint analysis of the photophysical properties of the studied systems and their photodecomposition quantum yields. It allows us to trace the influence of substituents, located in the diterpenoid skeleton and anthranilic fragment, on processes in both moieties of LC. Summarizing the data obtained, an inverse dependence of fluorescence and photodegradation quantum yields has been observed. This correlation established for LCs, in particular, allows one to propose a way to evaluate the photostability of potential drugs based on fluorescence analysis. This would be appropriate for compounds in which the reactivity depends on intersystem crossing, i.e. in the cases where the initial and reacting excited states differ in multiplicity.