20205-43-0

Basic information

• Product Name: 6,7-dimethylisatin
• Synonyms: 6,7-dimethylisatin;6,7-dimethyl-1H-indole-2,3-dione(SALTDATA: FREE)
• CAS NO: 20205-43-0
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 20205-43-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.25g/cm³
• Refractive Index: 1.586
• CAS DataBase Reference: 6,7-dimethylisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethylisatin(20205-43-0)
• EPA Substance Registry System: 6,7-dimethylisatin(20205-43-0)

Safety Data

• Hazardous Substances Data: 20205-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,7-dimethylisatin is used as a therapeutic agent for its anti-inflammatory, antioxidant, and antimicrobial properties, offering potential benefits in the treatment of various disorders.
Used in Cancer Treatment:
6,7-dimethylisatin is used as an anticancer agent, with studies suggesting its potential role in the treatment of various types of cancer due to its biological and pharmacological activities.
Used in Diabetes Management:
6,7-dimethylisatin is used as a potential treatment for diabetes, leveraging its pharmacological properties to manage the disease and its complications.
Used in Neurodegenerative Disease Treatment:
6,7-dimethylisatin is used as a therapeutic agent for neurodegenerative diseases, exploring its potential to mitigate the effects of such conditions.
Used in Agrochemical Production:
6,7-dimethylisatin is used as a synthetic intermediate in the production of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Chemical Synthesis:
6,7-dimethylisatin is used as a key intermediate in the synthesis of various pharmaceuticals, highlighting its utility in drug development and the chemical industry.

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

Upstream product

• 79-37-8 oxalyl dichloride 
• 302-17-0 chloral hydrate 
• 87-59-2 2,3-Dimethylaniline 
• 6579-44-8 2,3-dimethyl-α-isonitrosoacetanilide 

Downstream Products

• 50419-58-4 2-amino-3,4-dimethylbenzoic acid 
• 111395-36-9 2-(β-Anilinovinyl)-3-ethyl-6,7-dimethylindolo<3,2-d>thiazolium iodide 
• 1192112-00-7 6,7-dimethyl-3-hydroxy-3-(2-oxo-2-(4-bromophenyl)ethyl)-indolin-2-one 
• 1420468-13-8 2-(benzoylamino)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxylic acid 
• 1420468-17-2 (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide 
• 1420468-09-2 N-(6-benzoyl-2,3-dimethylphenyl)-2,2,2-trifluoroacetamide 
• 1420468-10-5 7,8-dimethyl-2-phenyl-2-(trifluoromethyl)-1,2-dihydro-4H-3,1-benzooxazin-4-one 
• 854020-54-5 (2-amino-3,4-dimethylphenyl)(phenyl)methanone 
• 1067187-33-0 3-hydroxy-7,8-dimethyl-2-(1-p-tolylcyclopropyl)quinoline-4-carboxylic acid 
• 1067186-58-6 2-(1-(4-chlorophenyl)cyclopropyl)-3-hydroxy-7,8-dimethylquinoline-4-carboxylic acid 
• 117570-93-1 2-<2-(carboxymethyl)phenoxy>-3,4-dimethylbenzoic acid 
• 117570-53-3 vadimezan 
• 129833-31-4 3,4-dimethyl-2-iodobenzoic acid 
• 76273-37-5 6,7-dimethyl-5H-1,2,4-triazino<5,6-b>indole-3(2H)-thione 

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.

Potent Synergy between Spirocyclic Pyrrolidinoindolinones and Fluconazole against Candida albicans

A spiroindolinone, (1S,3R,3aR,6aS)-1-benzyl-6′-chloro-5-(4-fluorophenyl)-7′-methylspiro[1,2,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-3,3′-1H-indole]-2′,4,6-trione, was previously reported to enhance the antifungal effect of fluconazole against Candida albicans. A diastereomer of this compound was synthesized, along with various analogues. Many of the compounds were shown to enhance the antifungal effect of fluconazole against C. albicans, some with exquisite potency. One spirocyclic piperazine derivative, which we have named synazo-1, was found to enhance the effect of fluconazole with an EC50 value of 300 pM against a susceptible strain of C. albicans and going as low as 2 nM against some resistant strains. Synazo-1 exhibits true synergy with fluconazole, with an FIC index below 0.5 in the strains tested. Synazo-1 exhibited low toxicity in mammalian cells relative to the concentrations required for antifungal synergy. Synergy from stereochemical complexity: An attempt to synthesize analogues of a known spiroindolinone led to a series of diastereomers. One spiroindolinone, termed synazo-1, was shown to exhibit potent activity (300 pM) against C. albicans in the presence of fluconazole. Synazo-1 is a true synergizer and was also highly active against some drug-resistant C. albicans strains.

2-Amino-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxylic acid (FlAib), a completely rigidified, fluoren-9-one-based α-amino acid

The synthesis, optical resolution, determination of absolute configuration and conformational preference, and spectroscopic characteristics of terminally protected (blocked) derivatives and short peptides of 2-amino-1,2,3,6- tetrahydro-6-oxocyclopenta[c]f

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.

CRYSTALLINE FORMS OF DMXAA SODIUM SALT

The present invention relates to pharmaceutically stable crystalline forms of (5, 6-Dimethyl-9- oxo-9H-xanthene-4-yl) acetic acid (DMXAA) sodium salt,- processes for preparing those stable crystalline forms; pharmaceutical compositions comprising at least one of those crystalline forms in solid form or in dissolved form and a pharmaceutically acceptable carrier. Disclosed are methods of using those pharmaceutical compositions to treat tumours, optionally in combination with other active pharmaceutical agents.

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.

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

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.

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.

Methods and compositions for selectin inhibition

The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selectins. In some embodiments, methods for treating selectin mediated