5192-04-1

Usage

Uses

Used in Pharmaceutical Industry:
7-Aminoindole is used as a reactant for the preparation of various pharmaceutical compounds, including:
1. Fluorescent anion receptors and sensors, which are essential tools in the detection and monitoring of anions in biological systems.
2. Sulfate receptors, which play a crucial role in the recognition and binding of sulfate ions, with potential applications in drug design and development.
3. Protein Kinase C θ (PKCθ) inhibitors, which are being investigated for their potential therapeutic effects in treating various diseases, including cancer and autoimmune disorders.
4. Factor Xa Inhibitors, which are important in the development of anticoagulant drugs for the prevention and treatment of blood clot-related conditions.
5. Aurora kinase inhibitors, which have potential applications in cancer therapy by targeting the Aurora kinase family, known to be involved in cell division and tumor growth.
6. Antagonists of the Mineralocorticoid Receptor, which can be used in the treatment of hypertension and other cardiovascular diseases.
7. Potent histone deacetylase (HDAC) inhibitors, which are being studied for their potential role in the treatment of various cancers by modulating gene expression.
8. TRPV1 antagonists, which have potential applications in the treatment of pain and inflammation.
9. Derivatives of N-(7-indolyl)benzenesulfonamide as cell cycle inhibitors, which are being investigated for their potential use in cancer therapy by disrupting cell cycle progression.

InChI:InChI=1/C8H8N2/c9-7-3-1-2-6-4-5-10-8(6)7/h1-5,10H,9H2

Upstream product

• 2942-37-2 8-nitrocinnoline 
• 6960-42-5 7-nitro-1H-indole 
• 51417-51-7 7-bromo-1H-indole 
• 253-66-7 Cinnoline 
• 96831-52-6 4-chloro-7-nitroindole 
• 528-29-0 1,2-Dinitrobenzene 
• 6293-87-4 o-nitrophenylhydrazine hydrochloride 
• 292853-66-8 2-(2-(2-nitrophenyl)hydrazono)propionic acid ethyl ester 
• 6960-45-8 7-nitro-1H-indole-2-carboxylic acid 
• 6960-46-9 ethyl 7-nitroindole-2-carboxylate 
• 4129-17-3 diphenylphosphoranyl azide 
• 61149-50-6 Ethyl pyruvate N-(5-methyl-2-nitrophenyl) hydrazone 
• 577-19-5 2-nitrophenyl bromide 
• 81524-76-7 7-azido-1H-indole 

Downstream Products

• 247186-87-4 4-chloro-N-(1H-indol-7-yl)benzenesulfonamide 
• 247186-85-2 N-(1H-indol-7-yl)-4-methoxybenzenesulfonamide 
• 165668-23-5 N-(7-indolyl)-4-nitrobenzenesulfonamide 
• 165669-24-9 4-cyano-N-(1H-indole-7-yl)benzenesulfonamide 
• 165669-28-3 N-(1H-indole-7-yl)-4-sulfamoylbenzenesulfonamide 
• 737801-80-8 (1H-indol-7-yl)carbamic acid benzyl ester 
• 1065237-08-2 7-amino-L-tryptophan 
• 1174734-62-3 C₁₅H₁₃N₃O 
• 959969-87-0 C₂₂H₁₈N₄O₂ 
• 1334246-10-4 (1-(5,8-Dimethyl-9H carbazol-1-yl)-3-phenylurea) 
• 1334246-11-5 (1-(5,8-Dimethyl-9H-carbazol-1-yl)-3-(4-methoxyphenyl)urea) 
• 1334246-13-7 (N-(5,8-Dimethyl-9H-carbazol-1-yl)-N-methyl-3-trifluoromethylbenzenesulfonamide) 
• 1348013-18-2 7-(3-biphenyl-4-yl-5-ethyl-4H-1,2,4-triazol-4-yl)-1H-indole 
• 1379535-57-5 (Z)-3-(1H-Indole-7-ylamino)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Self-assembling porous network nanostructure 7-aminoindole decorated reduced graphene oxide for high-performance asymmetric supercapacitor

The design and preparation of novel green and efficient energy storage electrode materials is a crucial way to solve the problem of intermittent energy storage of renewable energy. In this paper, the composite electrode materials of rGO decorated by organic 7-aminoindole (7-Ai) molecule with the characteristics of fast reversible redox kinetics are synthesized successfully. The modified 7-AirGOs composites can not only produce extra pseudocapacitance, which greatly improve the specific capacitance, but also form a stable mesoporous nanostructure to facilitate the diffusion and transport of ions. By investigating the influence of 7-Ai molecule content on the electrochemical performance of the composite electrodes, the 7-AirGO1 electrode is chosen as the optimum electrode, which exhibits a high specific capacitance of 425.73 F g?1 at 0.5 A g?1 and an excellent rate capability with the current density increased to 20 A g?1. Furthermore, the asymmetric supercapacitor assembled by the 7-AirGO1 and AC as positive and negative electrode respectively delivers an energy density of 14.60 W h kg?1 and a power density up to 10,500 W kg?1, as well as a cycling stability with a capacitance retention of 97.98% at a current density of 4 A g?1 for over 20,000 cycles. These results indicate that rGO-aminoindole composites are of great potential in flexible and wearable micro energy storage devices.

The halide binding behavior of 2-carbamoyl-7-ureido-l//-indoles: Conformational aspects

Indole-based anion receptors with an carboxamide unit in 2-and an urea in 7-position were prepared and found to bind halides (as well as acetate and nitrate) in chloroform solu-tions at room temperature. Investigations of the binding be-haviour show that the receptor is selective for chloride. Sur-prisingly, the truncated receptor 3 without the 2-carbamoyl substituent shows the highest affinity for Cl-. Thorough 1H, 13C and 15N NMR investigations indicate different binding modes for acetate, nitrate and halides to the receptor 2. The observation of a major conformational, change of this receptor during the binding of the halide ions leads to an understand-ing of the relative binding affinities of 3 > 4 > 2 for chloride. The results of the NMR study are supported by ab initio cal-culations. In addition, ESI FTICR MS competition experi-ments of the indole 2 and the quinoline 1 reveal the "self-aggregation" of the receptors and show that halides have a higher affinity to 2 than to 1.

Synthesis, structure and the binding properties of the amide-based anion receptors derived from 1H-indole-7-amine

Indole-7-amine was investigated as an alternative to aniline in construction of amide-based anion receptors. Replacement of aniline with indolamine introduces additional binding site-indolyl NH, which can enhance anion binding for more than five times. The molecular modelling of indole-containing receptors revealed the correlation between their conformational preferences and their affinity towards anions.

Cu-Catalyzed Directed C7?H Imidation of Indolines via Cross-Dehydrogenative Coupling

Cu(I)-catalyzed C7?H imidation of indolines via cross-dehydrogenative coupling is developed. The reaction involves C?H activation of indolines via six-membered metallacycle and various imides were coupled with indolines, with a broad substrate scope, and

Metal-induced pre-organisation for anion recognition in a neutral platinum-containing receptor

The presence of Pt(ii) allows pre-organisation of 4,4′- dicarboxamidoindole-2,2′-bipyridine, enhancing anion affinity with the resulting complex displaying selectivity for dihydrogen phosphate in DMSO-d 6-0.5% water. Moreover the Pt(ii) complex behaves as a colorimetic sensor for fluoride.

HFIP as Protonation Reagent and Solvent for Regioselective Alkylation of Indoles with All-Carbon Centers

The regio- and chemoselective construction of indole bearing an all-carbon center at the C3-position, a versatile bioactive building block, by C(sp2)-C(sp3) formation with olefins has been achieved through utilization of hexafluoroisopropanol (HFIP) as the protonation reagent and solvent. The catalytic reactions are operationally simple and green compared with previous reports utilizing elaborated olefins and catalysts. This protocol allows for alkylation of a variety of substituted indoles with diverse of styrene type alkenes in excellent yields and with high selectivity. Application of this protocol to the synthesis of drug was pursued and with an improved yield in contrast to previous art. Catalytic kinetics and deuterium-labeling experiments suggest that the rate-determining step involves the protonation of olefin by HFIP to generate carbocation, followed by electrophilic addition to indole derivative.

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets

Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.

Novel diarylamides and diarylureas with N-substitution dependent activity against medulloblastoma

Medulloblastoma – highly aggressive and heterogeneous tumours of the cerebellum – account for 15–20% of all childhood brain tumours, and are the most common high-grade childhood embryonal tumour of the central nervous system. Herein, potent in vitro antic

Ruthenium(II)-Catalyzed Direct C7-Selective Amidation of Indoles with Dioxazolones at Room Temperature

A protocol for the preparation of 7-amido indoles via regioselective C-H bond functionalization has been first accomplished under Ru(II) catalysis. Indole derivatives and 4-aryl/heteroaryl/benzyl/alkyl dioxzaolines containing various substituents were applicable for this transformation, readily providing the amidated indoles in moderate to good yields. This novel process has many advantages, including good compatibility with diverse functional groups, broad substrate scopes, and mild reaction conditions. Deuteration studies and control experiments have been performed to understand the mechanism of this transformation.