144024-36-2

Basic information

• Product Name: 1H-Indole, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-[(4-methylphenyl)sulfon yl]-, (S)-
• CAS NO: 144024-36-2
• Molecular Formula: C21H26N2O4S
• Molecular Weight: 402.514
• Mol File: 144024-36-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-[(4-methylphenyl)sulfon yl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-[(4-methylphenyl)sulfon yl]-, (S)-(144024-36-2)
• EPA Substance Registry System: 1H-Indole, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-[(4-methylphenyl)sulfon yl]-, (S)-(144024-36-2)

Safety Data

• Hazardous Substances Data: 144024-36-2(Hazardous Substances Data)

Usage

Chemical class

Indole derivative

Structural features

+ Sulfonyl group
+ Amino-propoxy group
+ Methylphenyl group
+ Hydroxy group

Stereochemistry

(S) enantiomer (left-handed configuration)

Potential properties

Pharmaceutical properties for drug development

Further research needed

Biological activities and potential applications

Upstream product

• 144024-34-0 (R)-(-)-3-<1-(4-methylphenyl)sulfonyl-4-indolyloxy>-1-<(4-methylphenyl)sulfonyloxy>-2-propanol 
• 75-31-0 isopropylamine 
• 144024-31-7 4,4-dimethoxy-1-<1-(4-methylphenyl)sulfonyl-3-pyrrolyl>-1-butanone 
• 144024-32-8 4-<1-(4-methylphenyl)sulfonyl-3-pyrrolyl>-4-oxobutanal 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 

Downstream Products

• 26328-11-0 (S)-pindolol 

Relevant articles and documents

Preparation of alkyl-substituted indoles in the benzene portion. Part 7. Synthesis of (±)- and (S)-(-)-pindolol

A new, short-step synthesis of a β-adrenergic blocking agent, pindolol, 1-(4-indolyloxy)-3-(2-propylamino)-2-propanol, is described. The acid-catalyzed indole cyclization reaction of 4-[1-(4-methylphenyl)sulfonyl-3-pyrrolyl]-4-oxobutanal (14) in the presence of (±)-3-chloro-1,2-propanediol (12) and (R)-1-O-[(4-methylphenyl)sulfonyl]glycerol (24) afforded (±)-1-chloro-3-[1-(4-methylphenyl)sulfonyl-4-indolyloxy]-2-propanol (15) and (R)-(-)-3-[1-(4-methylphenyl)sulfonyl-4-indolyloxy]-1-[(4-methylphenyl sulfonyloxy]-2-propanol (25). Reaction of these with isopropylamine and removal of the protecting group at the indole nitrogen gave (±)- and (S)-(-)-pindolol (3 and 4), thus constituting an efficient three-step synthesis of 3 and 4 from the readily available aldehyde (14).