15224-25-6

Usage

Uses

Used in Organic Chemistry:
3-Benzoylindole is used as a key intermediate in the synthesis of various organic compounds due to its unique structure and reactivity.
Used in Pharmaceutical Chemistry:
3-Benzoylindole is used as a building block for the development of new pharmaceutical drugs, leveraging its chemical properties to create novel therapeutic agents.
Used in Materials Science:
3-Benzoylindole is used as a component in the creation of advanced materials, such as dyes and plastics, where its chemical structure contributes to the desired properties of the final product.
Used in Research and Development:
3-Benzoylindole serves as a valuable compound in research settings, where its properties are further explored and understood to unlock new applications and uses in various industries.

InChI:InChI=1/C15H11NO/c17-15(11-6-2-1-3-7-11)13-10-16-14-9-5-4-8-12(13)14/h1-10,16H

Upstream product

• 120-72-9 indole 
• 925-90-6 ethylmagnesium bromide 
• 611-74-5 N,N-dimethylbenzamide 
• 19798-74-4 2-Ethoxy-2-phenyl-1,3-dioxolane 
• 98-88-4 benzoyl chloride 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 80360-19-6 phenyl(1-(phenylsulfonyl)-1H-indol-3-yl)methanone 
• 111122-98-6 3-(2-Phenyl-benzo[1,3]oxathiol-2-yl)-1H-indole 
• 82414-15-1 3-Phenyl-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid ethyl ester 
• 102652-00-6 (3-Indolyl)methoxyphenylcarbenium-tetrafluoroborat 
• 81581-98-8 1-[3-Acetyl-2-(1H-indol-3-yl)-2-phenyl-imidazolidin-1-yl]-ethanone 
• 91477-17-7 phenyl(1-tosyl-1H-indol-3-yl)methanone 
• 576-15-8 N-acetylindole 
• 2227-79-4 benzenecarbothioamide 

Downstream Products

• 19012-01-2 3-benzoyl-1-methylindole 
• 111562-63-1 2-(3-phenyl-1⁽²⁾H-pyrazol-4-yl)-aniline 
• 109678-22-0 2-cyano-3-(α-phenyl)indoleacetonitrile 
• 109662-80-8 3-benzoyl-1-diethylphosphonoindole 
• 109662-81-9 1-cyano-1-diethylphosphono-3-(α-phenyl)indoleacetonitrile 
• 91477-16-6 N-ethoxycarbonyl-3-benzoylindole 
• 67060-92-8 (1H-indole-1,3-diyl)bis(phenylmethanone) 
• 120-72-9 indole 
• 94-33-7 C₉H₁₀O₃ 
• 91477-18-8 N-methoxycarbonyl-3-benzoylindole 
• 91477-17-7 phenyl(1-tosyl-1H-indol-3-yl)methanone 
• 607-28-3 (E)-1H-indole-2,3-dione 3-oxime 
• 82414-25-3 3-benzoylindole, Z-oxime 
• 85729-25-5 N-(1H-indol-3-yl)benzamide 

Relevant academic research and scientific papers

A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.

[reaction--see text] Indoles are selectively acylated at the 3-position in high yields on treatment with a wide variety of acyl chlorides in CH(2)Cl(2) in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds under mild conditions and is applicable to indoles bearing various functional groups without NH protection.

Binding Mode and Structure–Activity Relationships of ITE as an Aryl Hydrocarbon Receptor (AhR) Agonist

Discovered as a modulator of the toxic response to environmental pollutants, aryl hydrocarbon receptor (AhR) has recently gained attention for its involvement in various physiological and pathological pathways. AhR is a ligand-dependent transcription factor activated by a large array of chemical compounds, which include metabolites of l-tryptophan (l-Trp) catabolism as endogenous ligands of the receptor. Among these, 2-(1′H-indole-3′-carbonyl)thiazole-4-carboxylic acid methyl ester (ITE) has attracted interest in the scientific community, being endowed with nontoxic, immunomodulatory, and anticancer AhR-mediated functions. So far, no information about the binding mode and interactions of ITE with AhR is available. In this study, we used docking and molecular dynamics to propose a putative binding mode of ITE into the ligand binding pocket of AhR. Mutagenesis studies were then instrumental in validating the proposed binding mode, identifying His 285 and Tyr 316 as important key residues for ligand-dependent receptor activation. Finally, a set of ITE analogues was synthesized and tested to further probe molecular interactions of ITE to AhR and characterize the relevance of specific functional groups in the chemical structure for receptor activity.

The Reactions of Electron-Rich Heterocycles with Derivatives of Orthocarboxylic Acids; VIII. Proton Acid-Catalyzed Acylation of Indoles by 2-Alkoxy-1,3-dioxolanes

In acid-catalyzed reactions with 3-unsubstituted indoles 1, 2-alkoxy-1,3-dioxolanes 2a-c behave as acyl equivalents.Depending on the substitution patterns of the reaction partners, the 1,3-dioxolanium ions 3a-c, generated in situ from the cyclic ortho esters by the action of sulfosalicylic acid, react to form tris-(3-indolyl)alkanes 6 and 9, bis-(3-indolyl)ethenes 7, or 3-benzoylindoles 8.Analogous reactivity was observed with related acyclic ortho esters.

Acylation of the zinc salt of indole

The indole Grignard reagent was transmetallated with ZnCl2 and the resulting zinc salt of indole was acylated with a number of acid chlorides and gave 3-acylindoles in yields superior to those obtained with the indole Grignard reagent.

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation

Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.

NbCl5 and AgClO4 promoted regio-selective acylation of indoles

In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.

METHODS OF TREATING CANCER

The present disclosure relates to methods of treating cancer in a patient using a combination of an inhibitor of an immune checkpoint protein and an indole compound or its phosphate derivative.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Synthesis of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates

An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.