79183-65-6

Basic information

• Product Name: 7-ETHYLISATIN
• Synonyms: 7-Ethyl-1H-indole-2,3-dione >98%;7-Ethylisatin;7-Ethyl-1H-indole-2,3-dione;7-ethyl-1H-indole-2,3-dione(SALTDATA: FREE);7-Ethylindoline-2,3-dione;ALD-N000069;NSC61828;1H-Indole-2,3-dione,7-ethyl-
• CAS NO: 79183-65-6
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 79183-65-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 193 °C(Solv: ethanol (64-17-5))
• Appearance: /
• Density: 1.247 g/cm³
• Refractive Index: 1.583
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.86±0.20(Predicted)
• CAS DataBase Reference: 7-ETHYLISATIN(CAS DataBase Reference)
• NIST Chemistry Reference: 7-ETHYLISATIN(79183-65-6)
• EPA Substance Registry System: 7-ETHYLISATIN(79183-65-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 79183-65-6(Hazardous Substances Data)

Usage

Uses

7-Ethyl-1H-indole-2,3-dione is used in the synthetic preparation of substituted indolin-2-ones as p90 ribosomal s6 protein kinase 2 (RSK2) inhibitors.

InChI:InChI=1/C10H9NO2/c1-2-6-4-3-5-7-8(6)11-10(13)9(7)12/h3-5H,2H2,1H3,(H,11,12,13)

Upstream product

• 302-17-0 chloral hydrate 
• 50522-37-7 2-ethylaniline hydrochloride 
• 7509-61-7 N-(2-ethylphenyl)-2-hydroxyiminoacetamide 
• 578-54-1 ortho-ethylaniline 

Downstream Products

• 5437-40-1 2-amino-3-ethylbenzoic acid 
• 41340-36-7 7-ethyl-2-(1H-indol-3-yl)ethan-1-ol 
• 1067186-32-6 8-ethyl-3-hydroxy-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid 
• 1067186-14-4 2-(1-(4-chlorophenyl)cyclopropyl)-8-ethyl-3-hydroxyquinoline-4-carboxylic acid 
• 1067187-06-7 8-ethyl-3-hydroxy-2-(1-(4-(trifluoromethyl)phenyl)cyclopropyl)quinoline-4-carboxylic acid 

Relevant articles and documents

Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid

The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.

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.

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.