6579-44-8

Basic information

• Product Name: N-(2,3-DIMETHYL-PHENYL)-2-HYDROXYIMINO-ACETAMIDE
• Synonyms: (2E)-N-(2,3-dimethylphenyl)-2-hydroxyiminoacetamide
• CAS NO: 6579-44-8
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• Mol File: 6579-44-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.14g/cm³
• Refractive Index: 1.552
• CAS DataBase Reference: N-(2,3-DIMETHYL-PHENYL)-2-HYDROXYIMINO-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,3-DIMETHYL-PHENYL)-2-HYDROXYIMINO-ACETAMIDE(6579-44-8)
• EPA Substance Registry System: N-(2,3-DIMETHYL-PHENYL)-2-HYDROXYIMINO-ACETAMIDE(6579-44-8)

Safety Data

• Hazardous Substances Data: 6579-44-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12N2O2/c1-7-4-3-5-9(8(7)2)12-10(13)6-11-14/h3-6,14H,1-2H3,(H,12,13)/b11-6+

Upstream product

• 302-17-0 chloral hydrate 
• 87-59-2 2,3-Dimethylaniline 
• 75-87-6 chloral 

Downstream Products

• 20205-43-0 6,7-dimethylisatin 
• 50419-58-4 2-amino-3,4-dimethylbenzoic acid 
• 129833-31-4 3,4-dimethyl-2-iodobenzoic acid 
• 117570-53-3 vadimezan 
• 117570-93-1 2-<2-(carboxymethyl)phenoxy>-3,4-dimethylbenzoic acid 

Relevant articles and documents

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

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.

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.