61640-20-8

Basic information

• Product Name: 1-(1-Methyl-1H-indol-5-yl)ethanone
• Synonyms: 1-(1-Methyl-1H-indol-5-yl)ethanone
• CAS NO: 61640-20-8
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21114
• Mol File: 61640-20-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(1-Methyl-1H-indol-5-yl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-Methyl-1H-indol-5-yl)ethanone(61640-20-8)
• EPA Substance Registry System: 1-(1-Methyl-1H-indol-5-yl)ethanone(61640-20-8)

Safety Data

• Hazardous Substances Data: 61640-20-8(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
1-(1-Methyl-1H-indol-5-yl)ethanone is used as a research chemical for studying the effects of serotonin receptor agonists on the brain and their potential applications in the treatment of various neurological and psychiatric disorders.
Used in Pharmaceutical Development:
Although its use as a recreational drug is prohibited, 1-(1-Methyl-1H-indol-5-yl)ethanone may be utilized in the development of new pharmaceuticals targeting serotonin receptors for the treatment of depression, anxiety, and other mood disorders.
Used in Forensic Toxicology:
1-(1-Methyl-1H-indol-5-yl)ethanone is used as a reference compound in forensic toxicology to identify and analyze the presence of this substance in biological samples, helping in the investigation of drug-related incidents and fatalities.

Upstream product

• 10075-52-2 5-bromo-1-methyl-H-indole 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 676-58-4 methylmagnesium chloride 
• 1011-65-0 5-methoxycarbonylindole 
• 128742-76-7 methyl 1-methyl-1H-indole-5-carboxylate 
• 53330-94-2 1-(1H-indol-5-yl)ethanone 
• 74-88-4 methyl iodide 

Relevant articles and documents

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Design, synthesis and anticancer properties of isocombretapyridines as potent colchicine binding site inhibitors

A series of novel isocombretapyridines were designed and synthesized based on a lead compound isocombretastatin A-4 (isoCA-4) by replacing 3,4,5-trimethoxylphenyl with substituent pyridine nucleus. The MTT assay results showed that compound 20a possessed the most potent activities against all tested cell lines with IC50 values at nanomolar concentration ranges. Moreover, 20a inhibited tubulin polymerization at a micromolar level and also displayed potent anti-vascular activity in vitro. Further mechanistic studies were conducted to demonstrate that compound 20a could bind to the colchicine site of tubulin,and disrupte the cell microtubule networks, induce G2/M phase arrest, promote apoptosis and depolarize mitochondria of K562 cells in a dose-dependent manner. Notably, 20a exhibited more potent tumor growth inhibition activity with 68.7% tumor growth inhibition than that of isoCA-4 in H22 allograft mouse model without apparent toxicity. The present results suggested that compound 20a may serve as a promising potent microtubule-destabilizing agent candidate for the development of therapeutics to treat cancer.

SUBSTITUTED (AZA)INDOLE DERIVATIVES

The invention relates to substituted (aza)indole derivatives, or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof, as well as to pharmaceutical compositions containing them and to their use as modulators of α7 nicotinic acetylcholine receptor activity in a mammalian subject. (I)

Mild Cu-Catalyzed Oxidation of Benzylic Boronic Esters to Ketones

The oxidation of benzylic boronic esters directly to the ketone is reported. This mild Cu-catalyzed method uses an ambient atmosphere of air as the terminal oxidant and is notably chemoselective. Oxidation of the C-B bond occurs selectively, even in the presence of unprotected alcohols. Initial investigation suggests the reaction proceeds through an alkylboron to Cu transmetalation, peroxide formation, and rearrangement to give the carbonyl.

Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System

We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)2 and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to α-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.