40281-54-7

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(1H-indol-3-yl)-2-phenylethanone is used as a key intermediate for the synthesis of various pharmaceuticals and organic compounds. Its unique structure and reactivity allow for the creation of a wide range of therapeutic agents.
Used in the Production of Psychoactive Substances:
In the field of psychopharmacology, 1-(1H-indol-3-yl)-2-phenylethanone serves as a precursor in the production of psychoactive substances such as MDMA (Ecstasy) and methamphetamine. Its role in these syntheses is crucial due to its ability to be transformed into the desired active compounds.
Used in the Synthesis of Natural Products and Biologically Active Compounds:
1-(1H-indol-3-yl)-2-phenylethanone has been identified as a potential intermediate in the synthesis of certain natural products and biologically active compounds. Its presence in these syntheses highlights its importance in the development of new and effective treatments for various medical conditions.
Used in Medicinal Chemistry Research:
As a compound with a rich chemical structure, 1-(1H-indol-3-yl)-2-phenylethanone is extensively utilized in medicinal chemistry research. It aids in the exploration of new drug candidates and the understanding of molecular interactions, contributing to the advancement of pharmaceutical science.

Upstream product

• 120-72-9 indole 
• 103-82-2 phenylacetic acid 
• 487-89-8 Indole-3-carboxaldehyde 
• 100-39-0 benzyl bromide 
• 584-08-7 potassium carbonate 
• 1539-57-7 diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 99445-26-8 indol-3-yl carboxylic acid imidazolide 
• 140-29-4 phenylacetonitrile 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 75698-48-5 3-(3-indolyl)-3-chloro-2-phenyl-2-propen-1-al 
• 85992-55-8 1-(1H-Indol-3-yl)-2-phenyl-ethanone oxime 
• 1428967-97-8 1-(1H-indol-3-yl)-2-((3-methoxyphenyl)amino)-2-phenylethanone 
• 1428972-67-1 N-(2-(1H-indol-3-yl)-2-oxo-1-phenylethyl)-2-chloro-N-(3-methoxyphenyl)acetamide 
• 1428968-99-3 N-(2-(1H-indol-3-yl)-2-oxo-1-phenylethyl)-2-(dimethylamino)-N-(3-methoxyphenyl)acetamide 
• 19620-89-4 2-bromo-1-(1H-indol-3-yl)-2-phenylethan-1-one 
• 5192-14-3 3-(2-phenylethyl)-1H-indole 
• 1428967-92-3 1-(1H-indol-3-yl)-2-phenyl-2-((3-(trifluoromethoxy)phenyl)amino)ethanone 
• 1428967-98-9 2-((3,5-difluorophenyl)amino)-1-(1H-indol-3-yl)-2-phenylethanone 
• 1428968-02-8 2-((3-fluoro-5-methoxyphenyl)amino)-1-(1H-indol-3-yl)-2-phenylethanone 

Relevant academic research and scientific papers

Early Drug-Discovery Efforts towards the Identification of EP300/CBP Histone Acetyltransferase (HAT) Inhibitors

EP300 and CBP (KAT3A/3B) are two highly homologous, multidomain, epigenetic coregulators that play central roles in transcription through the acetylation of lysine residues on histones and other proteins. Both enzymes have been implicated in human diseases, especially cancer. From a high-throughput screen of 191 000 compounds searching for EP300/CBP histone acetyltransferase (HAT) inhibitors, 18 compounds were characterized by a suite of biochemical enzymatic assays and biophysical methods, including X-ray crystallography and native mass spectrometry. This work resulted in the discovery of three distinct mechanistic classes of EP300/CBP HAT inhibitors, including two classes not previously described. The profiles of an example of each class of inhibitor are described in detail. A subsequent medicinal chemistry effort led to the development of a novel class of orally bioavailable AcCoA-competitive EP300/CBP HAT inhibitors with in vivo activity. We believe that this work will prove to be a useful guide for other groups interested in the development of HAT inhibitors.

Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

As a key element in the construction of complex organic scaffolds, the formation of C?C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C?C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.

P300/CBP HAT INHIBITORS

Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with histone acetyltransferase (HAT).

Discovery of Indole Derivatives as Novel and Potent Dengue Virus Inhibitors

3-Acyl-indole derivative 1 was identified as a novel dengue virus (DENV) inhibitor from a DENV serotype 2 (DENV-2) phenotypic antiviral screen. Extensive SAR studies led to the discovery of new derivatives with improved DENV-2 potency as well as activity in nanomolar to micromolar range against the other DENV serotypes. In addition to the potency, physicochemical properties and metabolic stability in rat and human microsomes were improved during the optimization process. Chiral separation of the racemic mixtures showed a clear preference for one of the two enantiomers. Furthermore, rat pharmacokinetics of two compounds will be discussed in more detail, demonstrating the potential of this new series of pan-serotype-DENV inhibitors.

Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl3

We report the FeCl3-mediated direct addition of electron-rich arenes to the C2-position of electrophilic N-Ac indoles under mild conditions (room temperature, air). No functional group is required on the arene nucleophile: one of its C-H bonds is added to the C2=C3 double bond of the indole nucleus in a Friedel-Crafts-type reaction. This dearomatisation process delivered a broad range of C2-arylated indolines.

Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones

Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

VIRAL REPLICATION INHIBITORS

The present invention relates to a series of novel compounds, methods to prevent or treat viral infections in animals by using the novel compounds and to said novel compounds for use as a medicine, more preferably for use as a medicine to treat or prevent viral infections, particularly infections with RNA viruses, more particularly infections with viruses belonging to the family of the Flaviviridae, and yet more particularly infections with the Dengue virus. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the novel compounds, to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of viral infections. The invention also relates to processes for preparation of the compounds.

Studies with azoles and benzoazoles: A novel simple approach for synthesis of 3-functionally substituted 3-acylindoles

(Chemical Equation Presented) 3-Substituted acylindoles 8 are obtained via refluxing carboxylic acids with indole in acetic anhydride solutions. The formed 3-substituted acylindole 8a is readily converted into 4-aminopyrazol-3- ylindoles 20, and into 22.

N-benzylindole and benzopyrazole derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunemodulating effect

The N-benzylindole- and benzopyrazole derivatives of the general formula 1 STR1 possess anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effect and are suitable for the preparation of medicaments.