92256-33-2

Basic information

• Product Name: Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-
• CAS NO: 92256-33-2
• Molecular Formula: C14H16N2O3
• Molecular Weight: 260.293
• Mol File: 92256-33-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-(92256-33-2)
• EPA Substance Registry System: Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-(92256-33-2)

Safety Data

• Hazardous Substances Data: 92256-33-2(Hazardous Substances Data)

Usage

Description

Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-, is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique chemical structure, which includes a butanoic acid backbone with an indole-containing ethylamine side chain attached to the 4-position. This structure endows it with potential applications in the development of therapeutic agents.

Uses

Used in Pharmaceutical Industry:
Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-, is used as a key intermediate in the synthesis of Canthin-6-one (C175635), an anticancer agent. It is particularly effective against cancer cells that exhibit multi-drug resistance, making it a valuable component in the development of cancer treatments.
Additionally, Butanoic acid, 4-[[2-(1H-indol-3-yl)ethyl]amino]-4-oxo-, is utilized in the synthesis of β-carbolinium compounds, which have demonstrated antimalarial properties. This application highlights its potential in contributing to the development of new treatments for malaria, a disease that continues to impact global health.

Upstream product

• 108-30-5 succinic acid anhydride 
• 61-54-1 tryptamine 
• 604-98-8 succinyl-coenzyme A 

Downstream Products

• 60755-87-5 canthin-6-one-3-N-oxide 
• 91147-07-8 3-(9H-Pyrido<3,4-b>indol-1-yl)propansaeure-methylester 
• 479-43-6 canthin-6-one 
• 92870-51-4 N'-<3-(methoxycarbonyl)propanoyl>tryptamine 

Relevant articles and documents

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Solution phase and nanoparticular biosynthetically inspired interconnections in the canthin-6-one β-carboline series and study of phenotypic properties on C. elegans

Based on the biosynthetic line of canthin-6-one alkaloids from their simple precursors such as tryptamine, the present work is focused on the study of alternative protocol of the Bischler-Napieralski reaction and has led to a full coverage of the different biosynthetic intermediates. Nanoparticles were also prepared as mimics of biosynthetic assembly lines and some interesting biological results in term of chemical ecology are also reported. Canthin-6-one, a particular representative β-carboline alkaloid, was targeted for synthesis keeping in mind its biosynthetic origin. In fact, several biosynthetic intermediates were synthesized and nanoparticular mimicry of key steps was also achieved permitting further evaluation of biological properties for this class of alkaloids. Copyright

Novel supramolecular palladium catalyst for the asymmetric reduction of imines in aqueous media

A novel approach to the asymmetric reduction of dihydro-β-carboline derivatives to the corresponding tetrahydro-β-carbolines is described based on the supramolecular lyophilized complex formed from β-cyclodextrin/ imines as an enzyme mimetic and palladium hydride as the reducing agent. The methodology allowed us to develop a short and efficient preparation of (R)-harmicine and (R)-deplancheine alkaloids in high overall yields and ee of 89 and 90%, respectively.