391-12-8

Usage

Uses

Used in Pharmaceutical Industry:
7-(Trifluoromethyl)indoline-2,3-dione is used as a pharmaceutical compound for its inhibitory effects on COX-1, COX-2, and β-catenin. This makes it a potential treatment option for various diseases, including lung cancer, diabetes, and Alzheimer's disease.
Used in Oncology:
In the field of oncology, 7-(Trifluoromethyl)indoline-2,3-dione is used as an inhibitor of COX-1 and COX-2 enzymes, which are involved in the development and progression of lung cancer. Its inhibitory action on these enzymes may help in controlling tumor growth and improving patient outcomes.
Used in Diabetes Treatment:
7-(Trifluoromethyl)indoline-2,3-dione is used as a potential therapeutic agent for diabetes due to its inhibitory effects on COX-1 and COX-2 enzymes. These enzymes are known to play a role in the development of insulin resistance, a key factor in the pathogenesis of diabetes. By inhibiting these enzymes, the compound may help in managing blood sugar levels and improving overall diabetes management.
Used in Alzheimer's Disease Treatment:
In the context of Alzheimer's disease, 7-(Trifluoromethyl)indoline-2,3-dione is used as an inhibitor of β-catenin, a protein involved in the regulation of gene expression and cell signaling. Its inhibitory action on β-catenin may help in reducing the neuroinflammation and neurodegeneration associated with Alzheimer's disease, potentially leading to improved cognitive function and disease progression.

InChI:InChI=1/C9H4F3NO2/c10-9(11,12)5-3-1-2-4-6(5)13-8(15)7(4)14/h1-3H,(H,13,14,15)

Upstream product

• 444-93-9 2-hydroxyimino-N-(2-trifluoromethyl-phenyl)-acetamide 
• 13061-96-6 dihydroxy-methyl-borane 
• 1067187-88-5 5-iodo-7-(trifluoromethyl)indoline-2,3-dione 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 444-93-9 (E)-2-(hydroxyimino)-N-(2-(trifluoromethyl)phenyl)acetamide 

Downstream Products

• 313-12-2 2-amino-3-(trifluoromethyl)benzoic acid 
• 64321-95-5 methyl 2-amino-3-trifluoromethyl-benzoate 
• 148887-60-9 2-(2-Fluoro-phenyl)-8-trifluoromethyl-quinoline-4-carboxylic acid 
• 18060-39-4 2-(4-Fluorphenyl)-8-trifluormethyl-cinchoninsaeure 
• 18193-08-3 2-phenyl-8-trifluoromethyl-quinoline-4-carboxylic acid 
• 18060-37-2 8-Trifluormethyl-2-(p-methoxy-phenyl)-cinchoninsaeure 
• 148887-62-1 2-(3,4-Dichloro-phenyl)-8-trifluoromethyl-quinoline-4-carboxylic acid 
• 72985-53-6 5-Trifluoromethyl-4H-benzo[1,4]oxazine-2,3-dione 
• 317-27-1 7-trifluoromethyl-indoline-2,3-dione-3-phenylhydrazone 
• 1067187-88-5 5-iodo-7-(trifluoromethyl)indoline-2,3-dione 
• 1067186-52-0 3-hydroxy-2-(1-phenylcyclopropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid 
• 1067187-37-4 3-hydroxy-2-(2-phenylpropan-2-yl)-8-(trifluoromethyl)quinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Benzenesulfonamide IDH mutant inhibitor, preparation method and application thereof

The invention discloses a benzenesulfonamide compound represented by a general formula (I) or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. Compared with the prior art, the benzenesulfonamide compound disclosed by the invention can be used as an isocitrate dehydrogenase 2 (IDH2) mutant inhibitor. According to the invention, pharmacological experiment results show that the compound disclosed by the invention has an obvious inhibiting effect on the activity of an IDH2 mutant (mIDH2), can effectively inhibit the process of catalyzing alpha-ketoglutaricacid to generate 2-hydroxyglutaric acid by mIDH2, and can be used for preventing and/or treating various related diseases including cancers and the like caused by IDH2 mutation.

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

Ylide mediated carbonyl homologations for the preparation of isatin derivatives

An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N-H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.

Novel inverse binding mode of indirubin derivatives yields improved selectivity for DYRK kinases

DYRK kinases are involved in alternative pre-mRNA splicing as well as in neuropathological states such as Alzheimer's disease and Down syndrome. In this study, we present the design, synthesis, and biological evaluation of indirubins as DYRK inhibitors wi

Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8- (trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury

Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure-activity studies in this series by branching at the α position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.

ORGANIC COMPOUNDS

The invention relates to organic compounds which have interesting pharmaceutical properties. In particular, the compounds are useful in the treatment and/or prevention of infections such as those caused by Plasmodium falciparum, Plasmodium vivax, Plasmodium malariae, Plasmodium ovale, Trypanosoma cruzi and parasites of the Leishmania genus such as, for example, Leishmania donovani. The invention also relates to pharmaceutical compositions containing the compounds, as well as processes for their preparation.

Methods and Compositions for Selectin Inhibition

The present teachings relate to compounds of formula I: wherein the constituent variables are defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating selectin me

Methods and Compositions for Selectin Inhibition

The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chemical library identified the quinoline salicylic acid class of compounds (1) as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLex. Through iterative medicinal chemistry, we identified analogues with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound 36 was efficacious in the rat AIA model of rheumatoid arthritis.

2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H] quinoline-4-carboxylic acid (PSI-697): Identification of a clinical candidate from the quinoline salicylic acid series of P-selectin antagonists

P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.