566200-64-4

Basic information

• Product Name: Acetic acid, [[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7- yl]oxy]-, methyl ester
• CAS NO: 566200-64-4
• Molecular Formula: C22H25ClN2O4
• Molecular Weight: 416.904
• Mol File: 566200-64-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Acetic acid, [[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7- yl]oxy]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7- yl]oxy]-, methyl ester(566200-64-4)
• EPA Substance Registry System: Acetic acid, [[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H-indol-7- yl]oxy]-, methyl ester(566200-64-4)

Safety Data

• Hazardous Substances Data: 566200-64-4(Hazardous Substances Data)

Upstream product

• 179819-98-8 methyl [3-(2-aminopropyl)-1H-indol-7-yloxy]acetate 
• 566200-65-5 [2-(3-chloro-phenyl)-2-hydroxy-ethyl]-[2-(7-hydroxy-1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 566200-63-3 2-[2-(7-benzyloxy-1H-indol-3-yl)-1-methyl-ethylamino]-1-(3-chloro-phenyl)-ethanol 
• 500138-65-8 3-[2-(tert-butoxycarbonyl)aminopropyl]-7-hydroxy-1H-indole 
• 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 
• 2380-86-1 6-hydroxy-1H-indole 
• 500138-64-7 7-benzyloxy-3-[2-(tert-butoxycarbonyl)aminopropyl]-1H-indole 
• 853021-90-6 methyl [3-[2-(tert-butoxycarbonyl)aminopropyl]-1H-indol-7-yloxy]acetate 
• 179819-91-1 methyl [3-(2-nitropropyl)-1H-indol-6-yloxy]acetate 
• 179819-70-6 methyl (1H-indol-6-yloxy)acetate 
• 115648-90-3 (S)-3-chlorostyrene oxide 

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.

INDOLE DERIVATIVES HAVING A 2 PHENYL-ETHANOLAMINO-SUBSTITUTED LOWER ALKYL GROUP AT THE 2- OR 3- POSITION THEREOF

An indole derivative of the formula: STR1 wherein R 1 is lower alkoxy, lower alkoxycarbonyl-lower alkoxy, carboxy-lower alkoxy, lower alkoxycarbonyl, phenyl-lower alkoxy, lower alkyl being optionally substituted by hydroxy, di-lower alkylaminosulfonyl, etc., R 2 is hydrogen, halogen, lower alkoxy, lower alkoxycarbonyl-lower alkoxy, carboxy-lower alkoxy, etc., R 3 is hydrogen or lower alkyl, R 4 is halogen or trifluoromethyl, R 5 is lower alkyl, or a salt thereof, these compounds being potent β 3-adrenergic receptor-stimulating agent with excellent adrenoceptor selectivity, and being useful in the prophylaxis or treatment of obesity or diabetes mellitus.