267-48-1

Usage

Uses

Used in Pharmaceutical Research:
5,6-METHYLENEDIOXYINDOLE is used as a research compound for its psychoactive properties, primarily in the development of treatments for mood disorders such as depression and anxiety. It is valued for its agonistic action on serotonin receptors, which is believed to contribute to its mood-altering effects.
Used in Neurodegenerative Disease Treatment:
In the field of neurology, 5,6-METHYLENEDIOXYINDOLE is explored as a potential therapeutic agent for neurodegenerative diseases. Its role in modulating serotonin receptor activity suggests it may have neuroprotective properties that could slow disease progression.
Used in Serotonin Receptor Function Studies:
5,6-METHYLENEDIOXYINDOLE is utilized as a tool in scientific research to study the function of serotonin receptors. Understanding the interaction between 5,6-METHYLENEDIOXYINDOLE and serotonin receptors can provide insights into the mechanisms of mood regulation and the development of new psychiatric medications.
Used in the Synthesis of Psychoactive Substances:
As a chemical precursor, 5,6-METHYLENEDIOXYINDOLE is used in the synthesis of various psychoactive substances. Its role in this process is crucial for the production of certain compounds with potential applications in medicine or that are subject to recreational use, thus necessitating strict regulatory oversight to prevent abuse.

InChI:InChI=1/C9H7NO2/c1-2-10-7-4-9-8(3-6(1)7)11-5-12-9/h1-4,10H,5H2

Upstream product

• 124201-30-5 trans-1-(3,4-(Methylenedioxy)-6-nitrophenyl)-2-nitroethene 
• 64-19-7 acetic acid 
• 77566-54-2 4-allyl-5-nitro-1,2-methylenedioxybenzene 
• 93577-94-7 3-(6-amino-benzo[1,3]dioxol-5-yl)-acrylic acid 
• 6315-90-8 4',5'-(methylenedioxy)-2-nitrocinnamic acid 
• 63375-82-6 2-(6-bromo-benzo[1,3]dioxol-5-yl)-ethylamine 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 80-73-9 1,3-dimethyl-2-imidazolidinone 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 100587-74-4 5-(benzenesulfonyl)-[1,3]dioxolo[4,5-f]indole 
• 333441-11-5 N-Benzo[1,3]dioxol-5-yl-benzenesulfonamide 
• 32996-27-3 4,5-methylenedioxy-2-nitrotoluene 

Downstream Products

• 98862-93-2 7-[1-(2,3-dimethoxy-phenyl)-2-nitro-ethyl]-5H-[1,3]dioxolo[4,5-f]indole 
• 100587-74-4 5-(benzenesulfonyl)-[1,3]dioxolo[4,5-f]indole 
• 113423-53-3 6,7,7-Tribromo-7H-[1,3]dioxolo[4,5-f]indole 
• 480435-99-2 3-(5,6-methylenedioxy-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
• 593267-73-3 4-(5H-[1,3]dioxolo[4,5-f]indol-7-ylmethyl)-3-methoxy-benzoic acid methyl ester 
• 562091-78-5 4-[1-(4-fluorophenyl)-5,6-methylenedioxy-1H-indol-3-yl]piperidine-1-carboxylic acid tert-butyl ester 
• 613679-41-7 5,6-methylenedioxy-1-(3',4',5'-trimethoxybenzoyl)indole 
• 1292799-35-9 1-({[5-(tert-butoxycarbonyl)-1,3-dioxolo[4,5-f ]indol-7-yl]methyl}methylamino)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 
• 1292799-38-2 1-{[(5H-1,3-dioxolo[4,5-f]indol-7-yl)methyl]methylamino}-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 
• 1034895-42-5 9-ING-41 
• 100587-76-6 5,6-methylenedioxy-1-benzenesulfonylindole-2-sulfonyl chloride 
• 100587-77-7 5,6-methylenedioxy-1-benzenesulfonyl-2-sulfamoylindole 
• 88048-40-2 1-[(5H-[1,3]dioxolo[4,5-f]indol-7-yl)-oxo-acetyl]-4-phenyl-piperazine 

Relevant academic research and scientific papers

Synthesis of 5,6-carbonyldioxyindole, a melanogenic cyclic carbonate ester of 5,6-dihydroxyindole

5,6-Carbonyldioxyindole (4), a melanogenic derivative of 5,6-dihydroxyindole (1), was synthesized by a procedure starting with 3,4-methylenedioxycinnamic acid. Compound 4 is a stable crystalline solid which is readily hydrolyzed to 1, a key intermediate on the biosynthetic pathway from tyrosine to melanin.

Preparation method of 5, 6-methylenedioxy indole

The invention provides a preparation method of 5, 6-methylenedioxy indole. The preparation method comprises the following steps: reacting 3, 4-methylenedioxy aniline serving as a raw material with benzene sulfonyl chloride to obtain A2, reacting A2 with 2, 2-dimethoxy-1-bromoethane to obtain a precursor A3 of a ring closing reaction, performing ring closing on A3 under the action of Lewis acid toobtain A4, and removing a protecting group of amino by using alkali to obtain the final 5, 6-methylenedioxy indole. according to the invention, 3, 4-methylenedioxy aniline is used as a raw material, nitro is prevented from being reduced into amino, the price of the compound is low, the cyclization reaction can be completed at normal temperature under the action of Lewis acid, and extreme conditions of high temperature or a strong reducing agent are avoided. The whole synthesis operation is simple, the post-treatment is easy, and the generated three wastes are few. The solvent in the reaction process can be reused, so that the cost is reduced, the operation is simple, the yield is higher, and the product with the purity of more than 98% can be obtained. The method is suitable for mass production and has obvious economic benefits.

INDOLE COMPOUND, OXIDATION DYE INTERMEDIATE, METHOD FOR PRODUCING INDOLE COMPOUND, AND METHOD FOR PRODUCING OXIDATION DYE-CONTAINING SOLUTION

PROBLEM TO BE SOLVED: To provide a novel indole compound to be a precursor of 5,6-dihydroxy indole, which has the nature of being easily oxidized and is, therefore, limited in its methods for production, a method for producing the indole compound, and a method for producing an oxidation dye-containing solution from the indole compound. SOLUTION: According to a method, a compound of formula (III) and boron trihalide are reacted to synthesize an indole compound, which is a boric acid ester of a 5,6-dihydroxy indole derivative. R1 and R2 independently represent H, a C1-C10 substituted/unsubstituted alkyl group, a C6-C10 substituted/unsubstituted aryl group, an oxygen-containing group, or a halogen atom; R3 is H, or a C1-C10 substituted/unsubstituted alkyl group; R4 and R5 independently represent H or a C1-C12 aliphatic group, or integrally represent a C1-C4 alkylene group. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

SOLID FORMS OF 3-(5-FLUOROBENZOFURAN-3-YL)-4-(5-METHYL-5H[1,3]DIOXOLO[4,5-F]INDOL-7-YL)PYRROLE-2,5-DIONE

The present disclosure relates to solid forms of 3-(5-Fluorobenzofuran-3-yl)-4-(5-methyl-5H-[1,3]dioxolo[4,5-f]indol-7-yl)pyrrole-2,5-dione, processes for preparation thereof, pharmaceutical compositions thereof, and uses thereof in treating disease.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

This invention relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating bacterial infections. This invention relates more particularly to compounds and pharmaceutical compositions thereof, methods of inhibiting H2S-producing enzymes with the compounds, and methods of treating bacterial infections with the compounds.

SOLID FORMS OF 3-(5-FLUOROBENZOFURAN-3-YL)-4-(5-METHYL-5H-[1,3]DIOXOLO[4,5-F]INDOL-7-YL)PYRROLE-2,5-DIONE

The present disclosure relates to solid forms of 3-(5-Fluorobenzofuran-3-yl)-4-(5-methyl-5H-[1,3]dioxolo[4,5-f]indol-7-yl) pyrrole-2,5-dione, processes for preparation thereof, pharmaceutical compositions thereof, and uses thereof in treating disease.

Tandem Wittig – Reductive annulation decarboxylation approach for the synthesis of indole and 2-substituted indoles

A simple tandem Wittig reaction-reductive decarboxylation route is established for the synthesis of indoles from commercially available o-nitrobenzaldehydes and a stable phosphorane. The method allows access to indoles in a very fast manner without involving any metal or expensive reagents or inert atmosphere. Also 2-substituted indoles are obtained which forms an important core of many biological active compounds.

Straight Access to Indoles from Anilines and Ethylene Glycol by Heterogeneous Acceptorless Dehydrogenative Condensation

The development of original strategies for the preparation of indole derivatives is a major goal in drug design. Herein, we report the first straight access to indoles from anilines and ethylene glycol by heterogeneous catalysis, based on an acceptorless dehydrogenative condensation, under noninert conditions. In order to achieve high selectivity, a combination of Pt/Al2O3 and ZnO have been found to slowly dehydrogenate ethylene glycol generating, after condensation with the amine and tautomeric equilibrium, the corresponding pyrrole-ring unsubstituted indoles.

Catalytic synthesis method of indole compounds

The invention discloses a catalytic synthesis method of indole compounds.The method includes the following steps of firstly, conducting stirring reaction on ortho-nitrostyrolene or derivatives of ortho-nitrostyrolene, bis(pinacolato)diboron, alkali and low-grade saturated monohydric alcohol under the atmosphere of nitrogen; secondly, cooling the reaction product in the first step to the room temperature, adding ethyl acetate to be sufficiently mixed, and washing with ethyl acetate after filtering; thirdly, spin-drying low-grade saturated monohydric alcohol in an organic phase of the material obtained in the second step, passing through a silica gel column, and drip washing the silica gel column with eluent composed of petroleum ether and ethyl acetate to obtain pure products, namely, the indole compounds.By means of the method, under the neutral conditions, bis(pinacolato)diboron low in price serves as the raw material, friendly low-grade saturated monohydric alcohol serves as the solvent, the indole compounds are obtained through simple operation, the raw materials are low in price and easy to obtain, efficiency and safety are high, and wide expandability and good industrial application prospects are achieved.

Synthesis of indoles from o,β-dinitrostyrenes via indium/acetic acid-mediated Reductive heterocyclizations

Reductive heterocyclization reactions of various 1-nitro-2-(2-nitroaryl) ethenes to indoles were investigated. In the presence of indium/AcOH in toluene or benzene, 1-nitro-2-(2-nitroaryl)ethenes were cyclized to give corresponding indoles in good yields.