16610-44-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-METHYLPHENYL)ANTHRANILIC ACID is used as an intermediate in the synthesis of pharmaceuticals for its anti-inflammatory and analgesic properties, contributing to the development of medications aimed at treating various medical conditions.
Used in Organic Compounds Synthesis:
N-(2-METHYLPHENYL)ANTHRANILIC ACID is used as an intermediate in the synthesis of other organic compounds, highlighting its versatility in chemical reactions and its role in creating a wide range of products.
Used in Dye and Pigment Production:
N-(2-METHYLPHENYL)ANTHRANILIC ACID is used in the production of dyes and pigments, taking advantage of its chemical properties to create a variety of colorants for different applications.

InChI:InChI=1/C14H13NO2/c1-10-6-2-4-8-12(10)15-13-9-5-3-7-11(13)14(16)17/h2-9,15H,1H3,(H,16,17)

Upstream product

• 16463-38-0 potassium 2-chlorobenzoate 
• 95-53-4 o-toluidine 
• 118-91-2 ortho-chlorobenzoic acid 
• 16497-87-3 potassium o-bromobenzoate 
• 7732-18-5 water 
• 860530-80-9 N-o-tolyl-anthranilic acid-anhydride 
• 88-67-5 2-Iodobenzoic acid 
• 584-08-7 potassium carbonate 
• 88-65-3 2-bromobenzoic-acid 

Downstream Products

• 3548-10-5 4-methyl-9-amino acridine 
• 1205-39-6 N-phenyl-2-methylaniline 
• 23592-62-3 phenyl(2-((2-methylphenyl)amino)phenyl)methanone 
• 1443543-35-8 4-methyl-N-benzylacridin-9-amine 
• 1446358-08-2 (2-(o-toluidino)phenyl)methanol 
• 1446358-10-6 N-(2-(chloromethyl)phenyl)-2-methylbenzenamine 
• 1446358-12-8 2-(2-(o-toluidino)phenyl)acetonitrile 
• 1446358-13-9 ethyl 2-(2-(o-tolylamino)phenyl)acetate 
• 1446358-15-1 ethyl 2-(2-(N-o-tolyl-N-tosylamino)phenyl)acetate 
• 1446358-19-5 1-(2-(N-o-tolyl-N-tosylamino)phenyl)-2-methylpropan-2-ol 
• 1446358-20-8 3-(2-(N-o-tolyl-N-tosylamino)benzyl)pentan-3-ol 
• 1446358-21-9 2-(2-(N-o-tolyl-N-tosylamino)phenyl)-1,1-diphenylethanol 
• 1446358-23-1 2-(2-(N-o-tolyl-N-tosylamino)phenyl)acetic acid 
• 1446358-30-0 4-methyl-11,11-diphenyl-10,11-dihydro-5H-dibenzo[b,f]azepine 

Relevant academic research and scientific papers

Synthesis of conformationally stable 1,8-diarylnaphthalenes: Development of new photoluminescent sensors for ion-selective recognition

Highly constrained 1,8-diarylnaphthalenes exhibiting stability to isomerization have been prepared utilizing two consecutive CuO-promoted Stille cross-couplings of 1,8-dibromonaphthalene and 4-alkyl-9-trimethylstannylacridines, Screening of Pd catalysts Pd(PPh 3)4, PdCl2dppf, or Pd2(dba) 3/t-Bu3P and bases such as Cy2NMe, t-BuOK, K3PO4, and Cs2CO3 in DME or DMF revealed superior results of Stille over Suzuki coupling with acridylboronic acids or pinacolate derivatives. The meso syn- and C2-symmetric antiisomers of 1,8-bis(4,4′-dimethyl-9,9′-diacridyl)naphthalene, 2, and 1,8-bis(4,4′-diisopropyl-9,9′-diacridyl)-naphthalene, 3, did not show any sign of syn/anti-interconversion after heating to 180 °C for 24 h, Using the Eyring equation, we calculated the Gibbs standard activation energy for isomerization, ΔGo?, to be higher than 180 kJ/mol. PM3 calculations of 2 and 3 suggest a highly congested structure exhibiting two parallel acridyl moieties perpendicular to the naphthalene ring. UV and fluorescence spectroscopy studies of 2 and 3 revealed remarkable quantum yields of these blue and green light emitters, Fluorescence titration experiments with the syn-isomer of 2 showed highly efficient quenching by Cu(II) ions, whereas almost no quenching effects were observed with Cu(I) and Zn(II) salts. The striking difference in fluorescence quenching was attributed to significant photoinduced electron transfer, resulting in nonradiative relaxation of excited Cu(II)-syn-2, Stern-Voelmer plots of syn-2 in the presence of CuCl2 showed a sigmoidal quenching curve indicating cooperative recognition, whereas a linear response was observed with CuCl and ZnCl2, Fluorescence experiments in the presence of various amounts of CuCl, CuBr, and Cu(ACN)4BF4 proved that the quenching is cation selective and independent of the nature of counteranions.

Synthesis of new bis- and tetra-acridines

A new series of bis- and tetra-acridines has been prepared from 4-(bromo-methyl)acridine; some of them exhibited encouraging in vitro cytotoxic activities against murine cell lines.

Design, synthesis and bioactivity evaluation of novel N-phenyl-substituted evodiamine derivatives as potent anti-tumor agents

Natural products are important sources for the development of therapeutic medicine, among which evodia fruit has a wide range of medicinal properties in traditional Chinese medicine. Evodiamine, the main active component of evodia fruit, has various anti-cancer effects and has been proved to be a Topo inhibitor. From our previous attempts of modifying evodiamine, we found that the N14 phenyl substituted derivatives had showed great anti-tumor activity, which prompted us to further explore the novel structures and activities of these compounds. Compound 6f, as a N14 3-fluorinated phenyl substituted evodiamine derivative, showed a certain inhibitory activity against Topo I at 200 μM. By studying its anti-tumor effects in vitro, compound 6f could inhibit proliferation and induce apoptosis, as well as arrest the cell cycle of HGC-27 and HT-29 cell lines at G2/M phase in a concentration-dependent manner. Moreover, compound 6f could inhibit the migration and invasion of HGC-27 cell lines. Meanwhile, compound 6f could induce apoptosis of HGC-27 cells by inhibiting PI3K/AKT pathway. Overall, this work demonstrated that the N14 phenyl-substituted evodiamine derivatives had a good inhibitory effect on tumor cells in vitro, providing a promising strategy for developing potential anticancer agents for the treatment of gastrointestinal tumors.

2-arylamine compound and preparation method and application thereof

The invention discloses a 2-arylamine compound and a preparation method and application thereof. The structure of the 2-arylamine compound is as shown in a formula I shown in the specification, wherein in the formula, the definition of each substituent group is as described in the specification and claims. The compound provided by the invention has a good inhibition effect on fatty acid binding protein 4, and can be used for prevention, treatment or adjuvant treatment of metabolic diseases, inflammations and cancers related to activity or expression of FABP4.

Design, synthesis and biological evaluation of N-anthraniloyl tryptamine derivatives as pleiotropic molecules for the therapy of malignant glioma

COX-2 and STAT3 are two key culprits in the glioma microenvironment. Herein, to inhibit COX-2 and block STAT3 signaling, we disclosed 27 N-anthraniloyl tryptamine compounds based on the combination of melatonin derivatives and N-substituted anthranilic acid derivatives. Among them, NP16 showed the best antiproliferative activity and moderate COX-2 inhibition. Of note, NP16 decreased the level of p-JAK2 and p-STAT3, and blocked the nuclear translocation of STAT3 in GBM cell lines. Moreover, NP16 downregulated the MMP-9 expression of BV2 cells in a co-culture system of BV2 and C6 glioma cells, abrogated the proliferative/invasive/migratory abilities of GBM cells, induced apoptosis by ROS and the Bcl-2-regulated apoptotic pathway, and induced obvious G2/M arrest in glioma cells in vitro. Furthermore, NP16 displayed favorable pharmacokinetic profiles covering long half-life (11.43 ± 0.43 h) and high blood-brain barrier permeability. Finally, NP16 effectively inhibited tumor growth, promoted the survival rate, increased the expression of E-cadherin and reduced overproduction of PGE2, MMP-9, VEGF-A and the level of p-STAT3 in tumor tissue, and improved the anxiety-like behavior in C6 glioma model. All these evidences demonstrated N-anthraniloyl tryptamine derivatives as multifunctional anti-glioma agents with high potency could drain the swamp to beat glioma.

Redox-neutral decarboxylative photocyclization of anthranilic acids

A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.

Design, synthesis and biological evaluation of novel phthalazinone acridine derivatives as dual PARP and Topo inhibitors for potential anticancer agents

In this study, we designed and synthesized a series of phthalazinone acridine derivatives as dual PARP and Topo inhibitors. MTT assays indicated that most of the compounds significantly inhibited multiple cancer cells proliferation. In addition, all the compounds displayed Topo II inhibition activity at 10 mol/L, and also possessed good PARP-1 inhibitory activities. Subsequent mechanistic studies showed that compound 9a induced remarkable apoptosis and caused prominent S cell cycle arrest in HCT116 cells. Our study suggested that 9a inhibiting Topo and PARP concurrently can be a potential lead compound for cancer therapy.

2,3-DIHYDROQUINAZOLIN COMPOUNDS AS NAV1.8 INHIBITORS

The present invention relates to Nav1.8 Inhibitor 2,3-dihydroquinazolin compounds of Formula (X); wherein Y', X', B', R1', R2', R3', R5', R6', R7', and z1 are as defined herein; or pharmaceutically acceptable salts or tautomer forms thereof, corresponding pharmaceutical compositions or formulations, methods or processes of compound preparation, methods, compounds for use in, uses for and/or combination therapies for treating pain and/or pain-related or associated disease(s), disorder(s) or condition(s), respectively.

NOVEL COMPOUND, COLORING COMPOSITION FOR DYEING OR TEXTILE PRINTING, INK FOR INK JET TEXTILE PRINTING, METHOD OF PRINTING ON FABRIC, AND DYED OR PRINTED FABRIC

Provided are a compound represented by any one of Formulae (1) to (3) described in the specification, a coloring composition for dyeing or textile printing including the compound, an ink for ink jet textile printing, a method of printing on fabric, and a dyed or printed fabric.

Design, synthesis and biological evaluation of 4-amidobenzimidazole acridine derivatives as dual PARP and Topo inhibitors for cancer therapy

PARP-1 could repair the DNA damages induced by Topo inhibitors, therefore inhibiting Topo and PARP-1 simultaneously might be able to overcome resistance and improve outcomes. In this study a series of 4-amidobenzimidazole acridines were designed and synthesized as dual Topo and PARP-1 inhibitors. Compound 11l displayed good inhibitory activities against Topo and PARP-1, as well as significantly inhibited cancer cells proliferation. Further mechanistic evaluations indicated that 11l treatment in MCF-7 cells induced accumulated DNA double-strand breaks, prompted remarkable apoptosis, and caused prominent G0/G1 cell cycle arrest. Moreover, 11l greatly suppressed tumor growth in mice, and displayed favorable metabolic properties in liver microsomes. Our study suggested that single agents inhibiting Topo and PARP concurrently might be an alternative for cancer therapy and 11l represented a potential lead compound for development of antitumor agents.