54-59-1

Basic information

• Product Name: N-(3-FLUOROPHENYL)ANTHRANILIC ACID
• Synonyms: N-(3-FLUOROPHENYL)ANTHRANILIC ACID;2-((3-fluorophenyl)amino)-benzoicaci;aciden-(3-flurophenyl)anthranilique;n-(m-fluorophenyl)-anthranilicaci;2-(3-FluorophenylaMino)benzoic acid, 98%;N-(3-Fluorophenyl)anthranilic acid, 2-(3-Fluoroanilino)benzoic acid;2-[(3-Fluorophenyl)amino]benzoicacid98%
• CAS NO: 54-59-1
• Molecular Formula: C₁₃H₁₀FNO₂
• Molecular Weight: 231.22
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 54-59-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 372.1 °C at 760 mmHg
• Flash Point: 178.8 °C
• Appearance: Pale yellow to gray/Powder
• Density: 1.342 g/cm³
• Vapor Pressure: 3.4E-06mmHg at 25°C
• PKA: 3.66±0.36(Predicted)
• CAS DataBase Reference: N-(3-FLUOROPHENYL)ANTHRANILIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-FLUOROPHENYL)ANTHRANILIC ACID(54-59-1)
• EPA Substance Registry System: N-(3-FLUOROPHENYL)ANTHRANILIC ACID(54-59-1)

Safety Data

• Hazard Codes: Xi
• RTECS: CB3060000
• Hazardous Substances Data: 54-59-1(Hazardous Substances Data)

Usage

General Description

N-(3-fluorophenyl)anthranilic acid is a chemical compound with the molecular formula C14H9FNO2. It is an anthranilic acid derivative and is commonly used in research and pharmaceutical applications. The compound is known for its potential therapeutic properties, particularly in the treatment of inflammation and pain. It is often used as a building block or precursor in the synthesis of various pharmaceutical compounds. N-(3-fluorophenyl)anthranilic acid is an important intermediate in the development of new drugs and has been the focus of several studies due to its potential pharmacological activities.

InChI:InChI=1/C13H10FNO2/c14-9-4-3-5-10(8-9)15-12-7-2-1-6-11(12)13(16)17/h1-8,15H,(H,16,17)/p-1

Upstream product

• 372-19-0 meta-fluoroaniline 
• 88-67-5 2-Iodobenzoic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 741280-99-9 methyl 2-(3-fluoroanilino)benzoate 

Downstream Products

• 500-41-4 3-fluoro-N-phenyl-aniline 

Relevant articles and documents

Design, synthesis and bioactivity evaluation of novel evodiamine derivatives with excellent potency against gastric cancer

Gastric cancer represents a significant health burden worldwide. Previously, inspired by the traditional Chinese medicine Wu-Chu-Yu to treat the spleen and stomach system for thousands of years, we identified N14-phenyl substituted evodiamine derivatives as potential antitumor agents with favorable inhibition on Top1. Herein, structural optimization and structure-activity relationship studies (SARs) led us to discovering a highly active evodiamine derivative compound 6t against gastric cancer. Further anti-tumor mechanism studies revealed that compound 6t played as the inhibition of topoisomerase 1 (Top1), effectively induced apoptosis, obviously arrested the cell cycle at the G2/M phase, and significantly inhibited the migration and invasion of SGC-7901 and MGC-803 cell lines in a dose-dependent manner. Moreover, the compound 6t was low toxicity in vivo and exhibited excellent anti-tumor activity (TGI = 70.12%) in the MGC-803 xenograft models. In summary, compound 6t represents a promising candidate as a potential chemotherapeutic agent against gastric cancer.

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.

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.