54-60-4

Usage

Uses

Used in Pharmaceutical Research:
N-(4-Fluorophenyl)anthranilic acid is used as a research compound for the development of potential drugs due to its unique properties and the presence of the fluorine atom on the phenyl group.
Used in Anti-Inflammatory and Analgesic Applications:
N-(4-Fluorophenyl)anthranilic acid is used as an anti-inflammatory and analgesic agent, as it has been studied for its potential in these therapeutic areas.
Used in Medicinal Chemistry:
N-(4-Fluorophenyl)anthranilic acid is used as a target compound in medicinal chemistry for the discovery of new compounds with potential biological activity.
Further research is ongoing to explore the potential applications of N-(4-Fluorophenyl)anthranilic acid in the field of medicine, as its properties and derivatives may offer new avenues for therapeutic intervention.

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

Upstream product

• 88-67-5 2-Iodobenzoic acid 
• 371-40-4 4-fluoroaniline 
• 7440-44-0 pyrographite 
• 118-91-2 ortho-chlorobenzoic acid 
• 91-56-5 indole-2,3-dione 
• 112934-62-0 1-(4-Fluorophenyl)-1H-indole-2,3-dione 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 88-65-3 2-bromobenzoic-acid 

Downstream Products

• 18201-71-3 2-((4-fluorophenyl)amino)benzamide 
• 131540-80-2 1-(4-fluorophenyl)-3-piperazino-1H-indole 
• 180912-03-2 1-(4-Fluoro-phenyl)-3-hydroxy-1H-indole-2-carboxylic acid methyl ester 
• 180911-98-2 2-[Cyanomethyl-(4-fluoro-phenyl)-amino]-benzoic acid 
• 180911-99-3 N-(4-fluorophenyl)-N-(2-carboxyphenyl)glycin 
• 180912-01-0 2-[(4-Fluoro-phenyl)-methoxycarbonylmethyl-amino]-benzoic acid methyl ester 
• 18201-87-1 2-[(4-fluorophenyl)amino]benzonitrile 
• 1207980-99-1 N-(4-(6,7-dimethoxyquinolin-4-yloxy)phenyl)-2-(4-fluorophenylamino)benzamide 
• 1207981-11-0 2-((4-fluorophenyl)amino)-N-(4-hydroxyphenyl)benzamide 
• 1239702-57-8 2-(4-fluorophenylamino)-N-(4-(3-(2-methylaminopyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide 
• 1370524-10-9 10-benzyloxycarbonyl-2-fluoro-9,10-dihydroacridine 

Relevant academic research and scientific papers

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 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.

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.

Structure-guided design and development of novel N-phenylpyrimidin-2-amine derivatives as potential c-Met inhibitors

The HGF/Met signaling pathway is over-expressed in many types of cancers and closely related to oncogenesis and metastasis. Thus, we developed novel N-phenylpyrimidin-2-amine derivatives to test their inhibitory activities towards c-Met kinase, and most o

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.

Synthesis and biological evaluation of acridine-based histone deacetylase inhibitors as multitarget agents against Alzheimer's disease

Multitarget agents simultaneously trigger molecules in functionally complementary pathways, and are therefore considered to have potential in effectively treating Alzheimer's disease (AD), which has a complex pathogenetic mechanism. In this study, the HDAC inhibitor core is incorporated into the acetylcholine esterase (ACE) inhibitor acridine–derived moiety and resulted in compounds that exhibited higher class IIa HDAC (4, 5, 7, and 9)- and class IIb HDAC6-inhibiting activity when compared to the pan-HDAC inhibitor SAHA in clinical practice. One of these compounds, 11b, displayed greater selectivity toward HDAC6 than other isoform enzymes. In contrast, the activity of compound 6a was selective toward class IIa HDAC and HDAC6. These two compounds exhibited strong activity against Aβ-aggregation as well as significantly disrupted Aβ-oligomer. Additionally, 11b and 6a strongly inhibited AChE. These experimental findings demonstrate that compounds 11b and 6a are HDAC-Aβ-aggregation-AChE inhibitors. Notably, they can enhance neurite outgrowth, but with no significant neurotoxicity. Further biological evaluation revealed the various cellular effects of multitarget compounds 11b and 6a, which have the potential to treat AD.

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 and synthesis of some acridine-piperazine hybrids for the improvement of cognitive dysfunction

A novel series of hybrid molecules (5a–5m) was designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against cognitive dysfunction. Heterocyclic moieties acridine and piperazine were conjugated with suitable linkers in a single scaffold, and the structures of the target compounds were confirmed by IR, 1H NMR, 13C NMR, and LC-MS analysis. The pharmacological activity of synthesized compounds was evaluated using behavioral models of amnesia viz. step-down passive avoidance and elevated plus maze at a dose 0.5?mg/kg as compared to standard rivastigmine. In vitro acetylcholinesterase (AChE) inhibition studies using brain homogenate of mice as the enzyme source revealed that most of the compounds exhibited a significant ability to inhibit the enzyme cholinesterase with compound 5c being the most potent (IC50 0.33?μm). Biochemical estimation of oxidative stress markers viz. plasma nitrite, thiobarbituric acid reactive substances, catalase, superoxide dismutase, and glutathione has been carried out using the respective assays to see the effect of the synthesized compounds on the scopolamine-induced oxidative damage. The molecular docking studies indicated the binding mode of the compounds to the catalytic site, peripheral site, and mid-gorge of AChE simultaneously. The calculated absorption, distribution, metabolism and excretion properties ensured the drug-likeness of the target compounds. The synthesized compounds were found to be potential cognitive enhancers, which were able to interfere with the scopolamine-induced oxidative stress also.

PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives

A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines: Rearrangements of isatins, acridines, and indoles

Efficient procedures for the synthesis of benzo-fluorinated dibenz[b,f]azepines (iminostilbenes) from fluorinated isatins or indoles using a number of ring-expansion reactions are described. A range of mono- and difluorinated analogues is accessible, and the syntheses can deliver gram quantities of the final products, which are precursors of fluoro analogues of the important anticonvulsant carbamazepine.