2475-81-2

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-amino-4-fluorobenzoate is used as a chemical intermediate for the synthesis of various drugs, leveraging its unique structural features to contribute to the development of novel therapeutic agents.
Used in Neurological Disorders Treatment:
Methyl 2-amino-4-fluorobenzoate is studied for its potential use in the treatment of neurological disorders, as its pharmacological properties may offer benefits in managing such conditions.
Used in Cancer Treatment:
Methyl 2-amino-4-fluorobenzoate has been investigated for its potential role in cancer treatment, with research exploring its effects on tumor growth and progression.
It is crucial to handle methyl 2-amino-4-fluorobenzoate with proper care and caution due to its potential health hazards if mismanaged.

InChI:InChI=1/C8H8FNO2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,10H2,1H3

Upstream product

• 67-56-1 methanol 
• 321-50-6 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 623588-40-9 methyl 5-chloro-4-fluoro-2-nitro-benzoate 
• 446-32-2 4-fluoroanthranilic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 144-55-8 sodium hydrogencarbonate 

Downstream Products

• 384-45-2 6-fluoro-1,2-benzisothiazol-3(2H)-one-1,1-dioxide 
• 791098-86-7 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-fluorobenzoic acid methyl ester 
• 612541-15-8 5-fluoro-2-cyanobenzenesulfonyl chloride 
• 612538-09-7 2-cyano-5-fluoro-N-(5-isopropyl-4-methyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 141541-80-2 (4-Fluoro-2-isobutylamino-phenyl)-methanol 
• 141541-38-0 5-fluoro-2-<(2-imidazolylthio)methyl>-N-isobutylaniline 
• 141541-55-1 5-fluoro-2-<(2-imidazolylsulfinyl)methyl>-N-isobutylaniline 
• 446-32-2 4-fluoroanthranilic acid 
• 328547-11-1 2-amino-5-fluoro-3-nitrobenzoic acid methyl ester 
• 1086685-11-1 methyl 4-fluoro-2-isothiocyanatobenzoate 
• 1157201-98-3 N-benzyl-5-fluoro-2-(methoxycarbonyl)aniline 
• 1197897-42-9 C₁₄H₁₁BrFNO₄S 
• 1312446-92-6 C₉H₆FNO₃ 
• 1350815-90-5 9-fluoro-2-(3,4-dimethoxyphenylamino)-5H-benzo[b]pyrimido[4,5-d]azepin-6(7H)-one 

Relevant academic research and scientific papers

Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene

Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.

Identification of potent and selective small molecule inhibitors of the cation channel TRPM4

Background and Purpose: TRPM4 is a calcium-activated non-selective cation channel expressed in many tissues and implicated in several diseases, and has not yet been validated as a therapeutic target due to the lack of potent and selective inhibitors. We sought to discover a novel series of small-molecule inhibitors by combining in silico methods and cell-based screening assay, with sub-micromolar potency and improved selectivity from previously reported TRPM4 inhibitors. Experimental Approach: Here, we developed a high throughput screening compatible assay to record TRPM4-mediated Na+ influx in cells using a Na+-sensitive dye and used this assay to screen a small set of compounds selected by ligand-based virtual screening using previously known weakly active and non-selective TRPM4 inhibitors as seed molecules. Conventional electrophysiological methods were used to validate the potency and selectivity of the hit compounds in HEK293 cells overexpressing TRPM4 and in endogenously expressing prostate cancer cell line LNCaP. Chemical chaperone property of compound 5 was studied using Western blots and electrophysiology experiments. Key Results: A series of halogenated anthranilic amides were identified with TRPM4 inhibitory properties with sub-micromolar potency and adequate selectivity. We also showed for the first time that a naturally occurring variant of TRPM4, which displays loss-of-expression and function, is rescued by the most promising compound 5 identified in this study. Conclusions and Implications: The discovery of compound 5, a potent and selective inhibitor of TRPM4 with an additional chemical chaperone feature, revealed new opportunities for studying the role of TRPM4 in human diseases and developing clinical drug candidates.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

QUINOLINES AND RELATED ANALOGS AS SIRTUIN MODULATORS

Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

Tandem C-O and C-N Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C-O and C-N bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.

Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: An efficient synthesis of 2-aminoquinolines

Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.

Discovery of novel bacterial RNA polymerase inhibitors: Pharmacophore-based virtual screening and hit optimization

The bacterial RNA polymerase (RNAP) is a validated target for broad spectrum antibiotics. However, the efficiency of drugs is reduced by resistance. To discover novel RNAP inhibitors, a pharmacophore based on the alignment of described inhibitors was used for virtual screening. In an optimization process of hit compounds, novel derivatives with improved in vitro potency were discovered. Investigations concerning the molecular mechanism of RNAP inhibition reveal that they prevent the protein-protein interaction (PPI) between σ70 and the RNAP core enzyme. Besides of reducing RNA formation, the inhibitors were shown to interfere with bacterial lipid biosynthesis. The compounds were active against Gram-positive pathogens and revealed significantly lower resistance frequencies compared to clinically used rifampicin.

QUINOLINONE DERIVATIVES

The present invention relates to compounds of the formula (I), salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds as activators of AMPK.

NOVEL 2,3-DIAMINO-QUINAZOLINONE DERIVATIVES AND THEIR MEDICAL USE

The present invention relates to novel 2,3-diamino-quinazolinone derivatives having medical utility, to use of the derivatives for the manufacture of a medicament, to pharmaceutical compositions comprising the derivatives, and to methods of treating a dis

NOVEL 2,3-DIAMINO-QUINAZOLINONE DERIVATIVES AND THEIR MEDICAL USE

This invention relates to novel 2,3-diamino-quinazolinone derivatives having medical utility, to use of the 2,3-diamino-quinazolinone derivatives of the invention for the manufacture of a medicament, to pharmaceutical compositions comprising the 2,3-diami