1128-47-8

Usage

Uses

Used in Pharmaceutical Industry:
6-Methyl-1H-indole-2,3-dione is used as a pharmaceutical compound for its anti-inflammatory, antibacterial, and antiviral properties, contributing to the development of new treatments for various diseases.
Used in Dye and Pigment Production:
In the chemical industry, 6-Methyl-1H-indole-2,3-dione is utilized as a key component in the synthesis of various dyes and pigments, owing to its unique chemical structure and color-yielding properties.
Used in Research and Development:
6-Methyl-1H-indole-2,3-dione is employed as a research compound for exploring its potential in treating neurological disorders and cancer, as well as for other therapeutic applications, due to its diverse biological activities and chemical reactivity.
Synthesis Methods:
6-Methyl-1H-indole-2,3-dione can be synthesized through the oxidation of indigo or by reacting 2-aminobenzoylformic acid with phosphorus oxychloride, providing a basis for its production and application in various industries.

InChI:InChI=1/C9H7NO2/c1-5-2-3-6-7(4-5)10-9(12)8(6)11/h2-4H,1H3,(H,10,11,12)

Upstream product

• 1132-29-2 2-hydroxyimino-N-m-tolylacetamide 
• 15219-34-8 Oxalyl bromide 
• 401585-34-0 oxalic acid-bis(3-tolylimidoyl)chloride 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 108-44-1 1-amino-3-methylbenzene 
• 3420-02-8 6-methylindole 
• 3551-75-5 N,N'-bis(3-methylphenyl)oxalamide 
• 131543-46-9 Glyoxal 
• 13194-69-9 2-iodo-5-methylaniline 
• 1165892-86-3 C₁₂H₁₃NO₃ 
• 1189052-02-5 4-methyl-2-nitro-1-[2-iodoethynyl]benzene 
• 302-17-0 chloral hydrate 
• 86911-82-2 2,3-dihydro-6-methyl-1H-indole 

Downstream Products

• 18595-17-0 methyl 4-methylanthranilate 
• 2305-36-4 4-methylanthranilic acid 
• 63480-11-5 7-methyl-2H-3,1-benzoxazine-2,4(1H)-dione 
• 1469872-12-5 2-(6-methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide 
• 816448-99-4 7-methylquinoline-4-carboxylic acid 
• 1334175-95-9 3'-amino-5-methyl-2,5',10'-trioxo-5',10'-dihydrospiro [indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2'-carbonitrile 
• 1391858-02-8 1-benzyl-6-methylindoline-2,3-dione 
• 1391858-22-2 (2'S,3'R,4'S)-5',5'-diethyl 3',4'-dimethyl 1-benzyl-6-methyl-2-oxospiro[indoline-3,2'-pyrrolidine]-3',4',5',5'-tetracarboxylate 
• 1315268-70-2 5'-methyl-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyrazolo[4,3-e]pyridine-4,3'-indoline]-2',5(10H)-dione 
• 1361403-84-0 ethyl 3-acetyl-9-benzyl-4-cyano-7-methyl-4,9-dihydropyrano[2,3-b]indole-4-carboxylate 

Relevant academic research and scientific papers

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

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.

Double Carbonylation Using Glyoxal (HCOCOH): A Practical Copper-Promoted Synthesis of Isatins from Primary and Secondary Anilines

A novel double carbonylation process has been demonstrated with easily available HCOCOH (glyoxal) as the double carbonylation reagent. Simple CuCl2?2H2O (copper(II) chloride dihydrate) was used as the oxidant for this transformation. Under optimized reaction conditions, various primary and secondary anilines were double-carbonylated to afford their corresponding isatins (26 examples, up to 80% yields). (Figure presented.).

An efficient method based on indoles for the synthesis of isatins by taking advantage of I2O5 as oxidant

An efficient method to synthesize isatins based on indoles by using inorganic hypervalent I2O5 has been explored in good yields, which successfully realized the transformation from indoles to isatins under metal-free, mild condition

A Palladium-Catalyzed Double Carbonylation Approach to Isatins from 2-Iodoanilines

A high-yielding procedure for the synthesis of isatins has been developed. Sequential Pd-catalyzed double carbonylation of 2-iodoanilines with near stoichiometric amounts of CO followed by acid-promoted cyclization readily affords an array of isatins. The conversion of 2-iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved adaptable to 13C-isotope labeling of isatins, which was extended to the synthesis of the 13C-isotope labeled antiviral drug metisazone and the experimental anti-schizophrenia drug ML137.

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.

Extended structure-activity relationship and pharmacokinetic investigation of (4-quinolinoyl)glycyl-2-cyanopyrrolidine inhibitors of fibroblast activation protein (FAP)

Fibroblast activation protein (FAP) is a serine protease related to dipeptidyl peptidase IV (DPPIV). It has been convincingly linked to multiple disease states involving remodeling of the extracellular matrix. FAP inhibition is investigated as a therapeutic option for several of these diseases, with most attention so far devoted to oncology applications. We previously discovered the N-4-quinolinoyl-Gly-(2S)-cyanoPro scaffold as a possible entry to highly potent and selective FAP inhibitors. In the present study, we explore in detail the structure-activity relationship around this core scaffold. We report extensively optimized compounds that display low nanomolar inhibitory potency and high selectivity against the related dipeptidyl peptidases (DPPs) DPPIV, DPP9, DPPII, and prolyl oligopeptidase (PREP) the log D values, plasma stabilities, and microsomal stabilities of selected compounds were found to be highly satisfactory. Pharmacokinetic evaluation in mice of selected inhibitors demonstrated high oral bioavailability, plasma half-life, and the potential to selectively and completely inhibit FAP in vivo.

Structure-based design, synthesis, andanticonvulsant activity of isatin-1-N-phenylacetamide derivatives

In an effort to develop the potent anticonvulsant agents, a series of novel isatin-1-N-phenylacetamide derivatives was synthesized and screened for their in vivo anticonvulsant activity against maximal electroshock test and evaluated for their neurotoxicity by the rotarod test at the same dose levels. Ten compounds exhibited the anticonvulsant activity. 2-(5-Methyl-2,3-dioxoindolin-1- yl)-N-phenylacetamide (4b) was found to be the most potent compound of the series with an ED50 of 91.3 mg/kg, TD50 of >1,000 mg/kg, a higher protective index (PI = TD50/ED50, >11) was gained than the reference drug phenobarbital and carbamazepine. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore. Springer Science+Business Media 2013.

Design, synthesis and antiproliferative activity evaluation of new 5-azaisoindigo derivatives

New 5-azaisoindigo derivatives were synthesized with two key intermediates 5-azaoxindole (7) and substituted indole-2,3-dione (10) in this paper. Intermediate 7 was prepared from 3-methylpyridine (1) through 6 steps containing oxidation reaction and so on. Intermediate 10 was obtained by a convenient Sandmeyer's method. The target compounds 5-azaisoindigo derivatives 11a-f were obtained by condensation of these two intermediates 7 and 10 in acidic condition. All target compounds were evaluated for their antiproliferative activity against seven cell lines by SRB assay. Compounds 11e and 11f showed significant antiproliferative activity against K562 cells (IC50: 8.9 μM and 13.6 μM, respectively).

Synthesis of isatins by I2/TBHP mediated oxidation of indoles

An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.