879-37-8

Usage

Uses

Used in Organic Synthesis:
3-Indoleacetamide is used as a key intermediate in the synthesis of complex organic molecules, such as the [5.5.6.6]diazafenestrane skeleton and indole-3-acetic acid. Its unique structure and reactivity make it a valuable building block for the development of novel compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
3-Indoleacetamide is used as a precursor in the synthesis of pharmaceutical compounds, particularly those with potential therapeutic applications. Its ability to be modified and incorporated into various molecular frameworks allows for the development of new drugs with improved efficacy and selectivity.
Used in Chemical Research:
3-Indoleacetamide is utilized in chemical research to study the properties and reactivity of the indole ring and its derivatives. This knowledge can be applied to the design and synthesis of new compounds with specific functions and applications in various fields, including materials science, agrochemicals, and environmental chemistry.

InChI:InChI=1/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)

Upstream product

• 239127-19-6 ethyl 3-indolylmethyl sulfide 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 50720-05-3 indolyl acetyl chloride 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 18443-04-4 3-indolylacetic acid ethyl imido ester hydrochloride 
• 63853-74-7 5-methoxypyrrolidin-2-one 
• 100-63-0 phenylhydrazine 
• 778-82-5 ethyl 3-indoleacetate 
• 61-54-1 tryptamine 
• 120-72-9 indole 
• 3638-64-0 1-nitroethylene 
• 150-90-3 sodium succinate 
• 2380-94-1 1H-indol-4-ol 
• 6986-48-7 bis-1-chloroethyl ether 

Downstream Products

• 61-54-1 tryptamine 
• 87-51-4 indole-3-acetic acid 
• 150114-41-3 1-methylindole-3-acetamide 
• 119139-23-0 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione 
• 219817-92-2 3-<4-(1-(methoxymethyl)-1H-2-(phenylthio)imidazol-5-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl>indole 
• 257874-86-5 2-(1-{3-[(tert-butyl)dimethylsilanyloxy]propyl}-1H-indol-3-yl)acetamide 
• 257876-71-4 2-{1-[(R)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide 
• 257875-28-8 2-{1-[(S)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide 
• 526-55-6 2-(3-indole)-ethanol 
• 1266346-01-3 3-(1H-indol-3-yl)-4-((4-methoxyphenyl)amino)pyrrole-2,5-dione 
• 1266346-02-4 3-(1H-indol-3-yl)-4-((4-morpholinophenyl)amino)pyrrole-2,5-dione 
• 257874-88-7 3-[1-(3-bromopropyl)-1H-indol-3-yl]-4-(phenylamino)-1H-pyrrole-2,5-dione 
• 257878-84-5 3-[1-(3-hydroxypropyl)-1H-indol-3-yl]-4-(phenylamino)-1H-pyrrole-2,5-dione 
• 257878-87-8 3-[1-(2-hydroxyethyl)-1H-indol-3-yl]-4-(phenylamino)-1H-pyrrole-2,5-dione 

Relevant academic research and scientific papers

Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex

Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished by its high activity and selectivity, wide substrate scope and modest reaction conditions. A variety of primary amines, RCH2NH2 (R = aliphatic, aromatic and heteroaromatic), are converted to the corresponding amides using ambient air as an oxidant in the presence of a sub-stoichiometric amount of KOtBu in tBuOH. A set of control experiments, Hammett relationships, kinetic studies and DFT calculations are undertaken to divulge mechanistic details of the amine oxidation using 1. The catalytic reaction involves abstraction of two amine protons and two benzylic hydrogen atoms of the metal-bound primary amine by the oxo and hydroxo ligands, respectively. A β-hydride transfer step for the benzylic C-H bond cleavage is not supported by Hammett studies. The nitrile generated by the catalytic oxidation undergoes hydration to afford the amide as the final product. This journal is

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

Molecular-docking-guided design and synthesis of new IAA-tacrine hybrids as multifunctional AChE/BChE inhibitors

A series of new indole-3-acetic acid (IAA)-tacrine hybrids as dual acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) inhibitors were designed and prepared based on the molecular docking mode of AChE with an IAA derivative (1a), a moderate AChE inhibitor identified by screening our compound library for anti-Alzheimer's disease (AD) drug leads. The enzyme assay results revealed that some hybrids, e.g. 5d and 5e, displayed potent dual in vitro inhibitory activities against AChE/BChE with IC50 values in low nanomolar range. Molecular modeling studies in tandem with kinetic analysis suggest that these hybrids target both catalytic active site and peripheral anionic site of cholinesterase (ChE). Molecular dynamic simulations and Molecular Mechanics/Poisson-Boltzmann Surface Area (MM-PBSA) calculations indicate that 5e has more potent binding affinity than hit 1a, which may explain the stronger inhibitory effect of 5e on AChE. Furthermore, their predicted pharmacokinetic properties and in vitro influences on mouse brain neural network electrical activity were discussed. Taken together, compound 5e can be highlighted as a lead compound worthy of further optimization for designing new anti-AD drugs.

[18F]MALEIMIDE-BASED GLYCOGEN SYNTHASE KINASE-3BETA LIGANDS FOR POSITRON EMISSION TOMOGRAPHY IMAGING AND RADIOSYNTHESIS METHOD

The present invention provides a compound having the structure: (Formula I), and a method of inhibiting Glycogen synthase kinase-3 β (GSK-3β) in a subject comprising administering to the subject said compound, so as to thereby inhibit the GSK-3β in the subject.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.

Direct reductive coupling of indoles to nitrostyrenes en route to (indol-3-yl)acetamides

A highly efficient one-pot method for the reductive coupling of indoles to nitrostyrenes in polyphosphoric acid doped with PCl3 was developed. This method allows direct and expeditious access to primary (indol-3-yl)acetamides, interesting as anti-cancer drug candidates.

Screening of NOS activity and selectivity of newly synthesized acetamidines using RP-HPLC

Nitric Oxide Synthase (NOS) inhibitors could play a powerful role in inflammatory and neurodegenerative diseases. In this work, novel acetamidine derivatives of NOS were synthesized and the inhibitor activity was evalued. To screen the activity and selectivity, the l-citrulline residue, after the enzymatic NOS assay, was derivatized with o-phthaldialdehyde/N-acetyl cysteine (OPA/NAC) and then evaluated by RP-HPLC method with fluorescence detection.All compounds did not affect the activity of endothelial and neuronal isoforms, while nine of them possessed a percentage of iNOS activity at 10 μM lower than 50%, and were selected for IC50 evaluation. Among them, a compound emerged as a very potent (IC50 of 53 nM) and selective iNOS inhibitor.

Selective aerobic hydrolysis of nitriles to amides using cobalt(II)/zinc

A novel protocol has been developed for the aerobic hydrolysis of nitriles to amides using cobalt(II)/zinc without using any strong acids and bases under solvent-free conditions. The reaction showed good performance for benzonitriles with sensitive groups such as ester and carboxylic acid.

Biotransformation of Indole to 3-Methylindole by Lysinibacillus xylanilyticus Strain MA

An indole-biotransforming strain MA was identified as Lysinibacillus xylanilyticus on the basis of the 16S rRNA gene sequencing. It transforms indole completely from the broth culture in the presence of an additional carbon source (i.e., sodium succinate). Gas-chromatography-mass spectrometry identified indole-3-acetamide, indole-3-acetic acid, and 3-methylindole as transformation products. Tryptophan-2-monooxygenase activity was detected in the crude extracts of indole-induced cells of strain MA, which confirms the formation of indole-3-acetamide from tryptophan in the degradation pathway of indole. On the basis of identified metabolites and enzyme assay, we have proposed a new transformation pathway for indole degradation. Indole was first transformed to indole-3-acetamide via tryptophan. Indole-3-acetamide was then transformed to indole-3-acetic acid that was decarboxylated to 3-methylindole. This is the first report of a 3-methylindole synthesis via the degradation pathway of indole.