244081-42-3

Basic information

• Product Name: 2-[[3-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxy-ethyl]amino]propyl]- 1H-indol-7-yl]oxy]acetic acid
• Synonyms: 2-[[3-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxy-ethyl]amino]propyl]- 1H-indol-7-yl]oxy]acetic acid;rafabegron
• CAS NO: 244081-42-3
• Molecular Formula: C₂₁H₂₃ClN₂O₄
• Molecular Weight: 402.87
• Mol File: 244081-42-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 665°Cat760mmHg
• Flash Point: 356°C
• Appearance: /
• Density: 1.345g/cm³
• Vapor Pressure: 1.36E-18mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-[[3-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxy-ethyl]amino]propyl]- 1H-indol-7-yl]oxy]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[3-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxy-ethyl]amino]propyl]- 1H-indol-7-yl]oxy]acetic acid(244081-42-3)
• EPA Substance Registry System: 2-[[3-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxy-ethyl]amino]propyl]- 1H-indol-7-yl]oxy]acetic acid(244081-42-3)

Safety Data

• Hazardous Substances Data: 244081-42-3(Hazardous Substances Data)

Usage

Chemical structure

Consists of an indole ring structure linked to an acetic acid molecule.

Explanation

Different sources of media describe the Explanation of 244081-42-3 differently. You can refer to the following data:
1. The core structure of the compound is an indole ring, which is connected to an acetic acid group, giving the molecule its unique properties.
2. The molecule has several chiral centers with the (2R) configuration, which contributes to its 3D structure and may influence its biological activity.
3. The compound's unique structure and functional groups make it of interest for potential biological activities, which could lead to applications in drug development and other areas of medicine.
4. The intricate structure of the molecule provides opportunities for researchers to explore its properties and potential uses in various fields, such as medicine and biotechnology.

Stereochemistry

Contains multiple (2R) stereocenters.

Functional groups

3-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxy-ethyl]amino]propyl] group.

Potential applications

Pharmaceutical research and drug development.

Opportunities for further investigation

Due to its complex structure and diverse functional groups.

InChI:InChI=1/C21H23ClN2O4/c1-13(23-11-18(25)14-4-2-5-16(22)9-14)8-15-10-24-21-17(15)6-3-7-19(21)28-12-20(26)27/h2-7,9-10,13,18,23-25H,8,11-12H2,1H3,(H,26,27)/t13-,18+/m1/s1

Upstream product

• 566200-66-6 3-[(2R)-(7-benzyloxy-1H-indol-3-yl)propyl]-(5R)-(3-chlorophenyl)-1,3-oxazolidin-2-one 
• 566200-63-3 2-[2-(7-benzyloxy-1H-indol-3-yl)-1-methyl-ethylamino]-1-(3-chloro-phenyl)-ethanol 
• 294178-11-3 7-benzyloxy-3-(2-nitro-1-propenyl)indole 
• 179819-93-3 (+/-)-3-(2-aminopropyl)-7-benzyloxyindole 
• 92855-65-7 7-(benzyloxy)-1H-indole-3-carbaldehyde 
• 20289-27-4 7-benzyloxyindole 
• 853022-60-3 (5R)-(3-chlorophenyl)-3-[(2R)-(7-hydroxy-1H-indol-3-yl)propyl]-1,3-oxazolidin-2-one 
• 853022-56-7 methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate 

Downstream Products

• 853022-56-7 methyl [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7-yloxy]acetate 

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.