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

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

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

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

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

Characterization of arylalkylamine n-acyltransferase from tribolium castaneum: an investigation into a potential next-generation insecticide target

The growing issue of insecticide resistance has meant the identification of novel insecticide targets has never been more important. Arylalkylamine N-acyltransferases (AANATs) have been suggested as a potential new target. These promiscuous enzymes are involved in the N-acylation of biogenic amines to form N-acylamides. In insects, this process is a key step in melanism, hardening of the cuticle, removal of biogenic amines, and in the biosynthesis of fatty acid amides. The unique nature of each AANAT isoform characterized indicates each organism accommodates an assembly of discrete AANATs relatively exclusive to that organism. This implies a high potential for selectivity in insecticide design, while also maintaining polypharmacology. Presented here is a thorough kinetic and structural analysis of AANAT found in one of the most common secondary pests of all plant commodities in the world, Tribolium castaneum. The enzyme, named TcAANAT0, catalyzes the formation of short-chain N-acylarylalkylamines, with short-chain acyl-CoAs (C2-C10), benzoyl-CoA, and succinyl-CoA functioning in the role of acyl donor. Recombinant TcAANAT0 was expressed and purified from E. coli and was used to investigate the kinetic and chemical mechanism of catalysis. The kinetic mechanism is an ordered sequential mechanism with the acyl-CoA binding first. pH-rate profiles and site-directed mutagenesis studies identified amino acids critical to catalysis, providing insights about the chemical mechanism of TcAANAT0. A crystal structure was obtained for TcAANAT0 bound to acetyl-CoA, revealing valuable information about its active site. This combination of kinetic analysis and crystallography alongside mutagenesis and sequence analysis shines light on some approaches possible for targeting TcAANAT0 and other AANATs for novel insecticide design.

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

USE OF CANTHIN-6-ONE AND ITS ANALOGS IN THE TREATMENT OF MYCOBACTERIA-LINKED PATHOLOGIES ( amended

The present invention relates to the use, for the preparation of a medicament intended for the treatment or the prevention of pathologies linked to, or caused by mycobacteria, of at least one of the compounds of the following formula (I): in which B represents in particular a nitrogen atom, and R1, R2, R3, R4, R5, R6, R7 and R8 represent in particular a hydrogen atom.

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.

Construction of the "left domain" of haplophytine

(Chemical Equation Presented) Left of the middle: Synthesis of the "left" structural domain (2) of haplophytine (1) features a stereoselective construction of its sterically congested carbon-carbon bond (C9′-C15) and an efficient cascade sequence involvin

Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities

Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities. 2005 American Chemical Society and American Society of Pharmacognosy.

The first total synthesis of bufobutanoic acid by two routes based on nucleophilic substitution reaction on indole nucleus

Regioselective nucleophilic substitution reaction of 1- hydroxytryptamines led to establish two novel routes for the first synthesis of bufobutanoic acid. An effective synthesis of 5-benzyloxytryptamine from tryptamine is also reported.