566200-31-5

Basic information

• Product Name: 1H-Indole-3-carboxaldehyde, 7-ethoxy-
• CAS NO: 566200-31-5
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Mol File: 566200-31-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-carboxaldehyde, 7-ethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-carboxaldehyde, 7-ethoxy-(566200-31-5)
• EPA Substance Registry System: 1H-Indole-3-carboxaldehyde, 7-ethoxy-(566200-31-5)

Safety Data

• Hazardous Substances Data: 566200-31-5(Hazardous Substances Data)

Usage

Derivative of indole

This compound is derived from indole, a heterocyclic compound commonly found in plants.

Contains an aldehyde and an ethoxy functional group

The molecule contains an aldehyde group (-CHO) and an ethoxy group (-OCH2CH3), which give it its unique chemical properties.

Used in organic synthesis

This compound is often used as a building block in organic synthesis, to create a variety of other chemical compounds.

Building block for pharmaceuticals and agrochemicals

The compound is used in the production of various pharmaceuticals and agrochemicals, making it an important substance in these industries.

Potential biological activities

1H-Indole-3-carboxaldehyde, 7-ethoxyhas been studied for its potential biological activities, including anti-inflammatory and cytotoxic effects.

Versatile compound

This compound has a range of potential applications in the chemical and pharmaceutical industries, making it a versatile substance.

Upstream product

• 2380-84-9 7-Indolol 
• 68-12-2 N,N-dimethyl-formamide 
• 927181-96-2 7-ethoxy-1H-indole 

Downstream Products

• 179819-92-2 3-(2-aminopropyl)-7-ethoxyindole 

Relevant articles and documents

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.