2447-16-7

Basic information

• Product Name: 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE
• Synonyms: 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE;2-(4-chloro-1H-indol-3-yl)ethanaMine;2-(4-chloro-1H-indol-3-yl)ethanaMine HCl;4-Chlorotryptamine
• CAS NO: 2447-16-7
• Molecular Formula: C10H11ClN2
• Molecular Weight: 194.6607
• Mol File: 2447-16-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 375.7°Cat760mmHg
• Flash Point: 181°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 7.61E-06mmHg at 25°C
• Refractive Index: 1.675
• PKA: 16.31±0.30(Predicted)
• CAS DataBase Reference: 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE(2447-16-7)
• EPA Substance Registry System: 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE(2447-16-7)

Safety Data

• Hazardous Substances Data: 2447-16-7(Hazardous Substances Data)

Usage

General Description

2-(4-Chloro-1H-indol-3-yl)-ethylamine is a chemical compound with the molecular formula C10H11ClN2. It is a derivative of indole, which is a heterocyclic aromatic compound that is commonly found in plant-based compounds and pharmaceuticals. 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE is an ethylamine derivative of 4-chloroindole, and it is used in the synthesis of various pharmaceutical drugs and research chemicals. It has potential applications in the field of medicinal chemistry and drug development, and its structural features make it a valuable building block for the creation of novel chemical compounds with biological activity. Additionally, this compound may have biological properties that are yet to be fully explored and utilized for various applications.

InChI:InChI=1/C10H11ClN2/c11-8-2-1-3-9-10(8)7(4-5-12)6-13-9/h1-3,6,13H,4-5,12H2

Upstream product

• 27542-41-2 (S)-2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid 
• 1452838-23-1 (E)-4-chloro-3-(2-nitrovinyl)-1H-indole 
• 876-72-2 4-chloroindole-3-carboxaldehyde 
• 25235-85-2 4-chloro-1H-indole 

Relevant articles and documents

Facile in Vitro Biocatalytic Production of Diverse Tryptamines

Tryptamines are a medicinally important class of small molecules that serve as precursors to more complex, clinically used indole alkaloid natural products. Typically, tryptamine analogues are prepared from indoles through multistep synthetic routes. In the natural world, the desirable tryptamine synthon is produced in a single step by l-tryptophan decarboxylases (TDCs). However, no TDCs are known to combine high activity and substrate promiscuity, which might enable a practical biocatalytic route to tryptamine analogues. We have now identified the TDC from Ruminococcus gnavus as the first highly active and promiscuous member of this enzyme family. RgnTDC performs up to 96 000 turnovers and readily accommodates tryptophan analogues with substituents at the 4, 5, 6, and 7 positions, as well as alternative heterocycles, thus enabling the facile biocatalytic synthesis of >20 tryptamine analogues. We demonstrate the utility of this enzyme in a two-step biocatalytic sequence with an engineered tryptophan synthase to afford an efficient, cost-effective route to tryptamines from commercially available indole starting materials.

PYRAZOLE AMIDE DERIVATIVE

The present invention relates to a novel compound having a function of inhibiting RORγ activity. The present invention also relates to pharmaceutical composition comprising the compound, a use of the compound in treating or preventing autoimmune diseases, inflammatory diseases, metabolic diseases, or cancer diseases.

Discovery of a novel and potent human and rat β3-adrenergic receptor agonist, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl] -1H-indol-7-yloxy]acetic acid

In search for potent and selective β3-adrenergic receptor (β3-AR) agonists as potential drugs for the treatment of type II diabetes and obesity, a novel series of 1-(3-chlorophenyl)-2-aminoethanol derivatives were prepared and evaluated for their biological activity at human β1-, β2-, and β3-ARs and rat β3-AR expressed in Chinese hamster ovary (CHO) cells. Replacement of the right-hand side (RHS, benzene ring) in the 'first generation' β3-AR agonists BRL 37344 and CL 316243 with a 1H-indole ring gave compound 31 with unique pharmacological properties among β3-AR agonists. Initial in vitro assays showed that 31 possesses modest rat and human β3-ARs agonistic activity. Introduction of various substituent into the indole nucleus of 31 afforded a number of compounds with good β3-ARs agonistic activity. In particular, 90 having a carboxylic acid functionality at the 7-position of the indole nucleus showed the most potent human β3-AR agonistic activity. Finally, optical resolution of 90 led to the identification of the most promising compound, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H- indol-7-yloxy]acetic acid (96, AJ-9677). This compound exhibited potent human β3-AR agonistic activity (EC50 = 0.062 nM, IA = 116%) with 210- and 103-fold selectivity over human β2-AR and β1-AR, respectively. Compound 96 also exhibited potent rat β3-AR agonistic activity (EC50 = 0.016 nM, IA = 110%). Moreover, repeated oral administration of 96 inhibited body weight gain and significantly decreased glucose, insulin, free fatty acid, and triglyceride concentrations in plasma in KK-Ay/Ta mice. On the basis of this pharmacological profile, 96 entered clinical development as a drug for the treatment of type II diabetes and obesity.