61500-87-6

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-TRIFLUOROMETHYL-BENZOIC ACID METHYL ESTER is used as a chemical intermediate for the preparation of quinazolinedione sulfonamides. These compounds act as competitive AMPA receptor antagonists, which are being investigated for their potential in treating neurological disorders such as epilepsy and neurodegenerative diseases.
Additionally, 2-AMINO-4-TRIFLUOROMETHYL-BENZOIC ACID METHYL ESTER is utilized in the synthesis of (arylamino)pyrimidobenzazepinones and pyrimidobenzazepinethiones. These compounds are inhibitors of polo-like kinase 1, an enzyme that plays a critical role in cell division and has been implicated in the progression of various cancers. As a result, these synthesized compounds are considered potential antitumor agents, offering new avenues for cancer treatment and therapy development.

InChI:InChI=1/C9H8F3NO2/c1-15-8(14)6-3-2-5(4-7(6)13)9(10,11)12/h2-4H,13H2,1H3

Upstream product

• 67-56-1 methanol 
• 402-13-1 2-amino-4-trifluoromethylbenzoic acid 
• 98-16-8 3-trifluoromethylaniline 
• 228418-45-9 methyl 2-nitro-4-trifluoromethylbenzoate 
• 320-94-5 2-nitro-4-trifluoromethylbenzoic acid 
• 872624-52-7 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester 
• 404-83-1 N-(3-trifluoromethylphenyl)-2-oxyiminoacetamide 
• 343-69-1 6-(Trifluoromethyl)-1H-indol-2,3-dione 
• 97928-01-3 7-trifluoromethyl-1,2-dihydro-3,1-benzoxazine-2,4-dione 
• 186581-53-3 diazomethane 

Downstream Products

• 869550-68-5 methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate 
• 913299-81-7 methyl 2,3-diamino-4-(trifluoromethyl)benzoate 
• 913299-80-6 methyl 2-amino-3-nitro-4-(trifluoromethyl)benzoate 
• 913299-79-3 methyl 2-(acetylamino)-3-nitro-4-(trifluoromethyl)benzoate 
• 873006-01-0 2-iodo-4-(trifluoromethyl)benzaldehyde 
• 873005-49-3 (2-iodo-4-(trifluoromethyl)phenyl)methanol 
• 1236303-09-5 methyl 2-iodo-4-(trifluoromethyl)benzoate 
• 1427400-33-6 2-amino-5-iodo-4-(trifluoromethyl)benzoic acid 
• 1228960-69-7 2-[[5-[3-(dimethylamino)propyl]-2-methyl-3-pyridinyl]amino]-5,7-dihydro-9-(trifluoromethyl)-6H-pyrimido[5,4-d][1]benzazepine-6-thione 

Relevant academic research and scientific papers

Synthesis and pharmacological studies at the Gly/NMDA, AMPA and Kainate receptors of new oxazolo[4,5-c]quinolin-4-one derivatives bearing different substituents at position-2 and on the fused benzo ring

The synthesis and biological evaluation at the Gly/NMDA, AMPA and Kainate receptors of new oxazolo[4,5-c]quinolin-4-one derivatives are reported. Different substituents were introduced at the 2-position (mercapto, carbonyl and methyl groups) and on the fu

Discovery of Icenticaftor (QBW251), a Cystic Fibrosis Transmembrane Conductance Regulator Potentiator with Clinical Efficacy in Cystic Fibrosis and Chronic Obstructive Pulmonary Disease

Mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) ion channel are established as the primary causative factor in the devastating lung disease cystic fibrosis (CF). More recently, cigarette smoke exposure has been shown to be asso

Pyrazole derivative for FGFR inhibitor and preparation method of pyrazole derivative

The invention provides a pyrazole derivative for an FGFR inhibitor and a preparation method of the pyrazole derivative. The invention specifically relates to an amide pyrazole compound serving as an FGFR irreversible inhibitor, and a preparation method and application thereof. The present invention provides a compound as shown in Formula I, or a pharmaceutically acceptable salt, or solvate, isotope substitute, prodrug, or metabolite thereof. The compound as shown in general formula I have FGFR inhibitory activity, and is capable of preventing or treating disorders associated with FGFR activityor expression, preferably such as cancer.

Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists

Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here we analyzed structure-activity relationships of a battery of 36 non-steroidal structural variants of methyl anthranilate including 23 synthesized compounds. We identified structural requirements that lead to more potent AR antagonists. Specific compounds inhibit the transactivation of wild-type AR as well as AR mutants that render treatment resistance to hydroxyflutamide, bicalutamide and the second-generation AR antagonist enzalutamide. This suggests a distinct mode of inhibiting the AR compared to the clinically used compounds. Competition assays suggest binding of these compounds to the AR ligand binding domain and inhibit PCa cell proliferation. Moreover, active compounds induce cellular senescence despite inhibition of AR-mediated transactivation indicating a transactivation-independent AR-pathway. In line with this, fluorescence resonance after photobleaching (FRAP) - assays reveal higher mobility of the AR in the cell nuclei. Mechanistically, fluorescence resonance energy transfer (FRET) - assays indicate that the amino-carboxy (N/C)-interaction of the AR is not affected, which is in contrast to known AR-antagonists. This suggests a mechanistically novel mode of AR-antagonism. Together, these findings indicate the identification of a novel chemical platform as a new lead structure that extends the diversity of known AR antagonists and possesses a distinct mode of antagonizing AR-function.

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.

SULFONYLAMINOBENZAMIDE COMPOUND AND PEST CONTROL AGENT

A compound represented by formula (I) or a salt thereof. In formula (I), R1 and R4 each independently represent a hydrogen atom, or an unsubstituted or substituted C1 to C6 alkyl group or the like. R2 represents a hydrogen

Design, synthesis and insecticidal activities of novel anthranilic diamides containing fluorinated groups as potential ryanodine receptors activitors

In order to search for novel potent and environmentally benign insecticides, a series of anthranilic diamides containing various fluorinated groups were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, s

Design and Synthesis of Selurampanel, a Novel Orally Active and Competitive AMPA Receptor Antagonist

A series of potent quinazolinedione sulfonamide antagonists of the α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptor were designed and synthesized. The structure–activity relationships (SAR) and in vivo activity of the series were investigated. In particular, compound 1 S (selurampanel; N-[7-isopropyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1H-quinazolin-3-yl]methanesulfonamide) has shown excellent oral potency against maximal electroshock seizure (MES)-induced generalized tonic–clonic seizures in rodents as well as significant activity in patients suffering from various forms of epilepsy. The X-ray crystal structure of selurampanel bound to the AMPA receptor hGluA was also obtained.

HCV NS3 protease inhibitors

The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

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.