2447-16-7

Usage

Uses

Used in Pharmaceutical Drug Synthesis:
2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE is used as a key intermediate in the synthesis of pharmaceutical drugs for its ability to contribute to the development of novel chemical compounds with potential therapeutic effects.
Used in Research Chemicals:
In the field of research, 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE is used as a building block for creating new chemical entities that can be studied for their biological activity and potential applications in medicine.
Used in Medicinal Chemistry:
2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE is utilized as a structural component in medicinal chemistry to design and develop new drugs with improved efficacy and selectivity.
Used in Drug Development:
In the pharmaceutical industry, 2-(4-CHLORO-1H-INDOL-3-YL)-ETHYLAMINE is used as a precursor in drug development to facilitate the creation of innovative medications that address unmet medical needs.

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

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

Relevant academic research and scientific papers

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.

Method for preparing chlorine substituted indole derivative

The invention discloses a method for preparing a chlorine substituted indole derivative 2-(4-chloro-1H-indol-3-yl)-ethyl carbamate. The method comprises the following steps: by taking 4-chloroindole as an initial raw material, carrying out a Friedel-crafts reaction, amidation, reduction and t-butyloxycarboryl protection reaction, thereby obtaining the target product. The compound is an important medical intermediate.

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.

Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade

A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization proc

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.