87084-40-0

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-1-(1H-INDOL-3-YL)-ETHANONE is used as a precursor in the synthesis of serotonin and melatonin for the development of therapeutic agents targeting conditions related to these neurotransmitters and hormones. Its involvement in the regulation of mood and sleep makes it a potential candidate for treating sleep disorders and mood disorders.
Used in Neurotransmitter Research:
In the field of neuroscience, 2-AMINO-1-(1H-INDOL-3-YL)-ETHANONE is utilized as a research compound to study the biosynthesis and functions of serotonin and melatonin. Understanding its role in neurotransmission can lead to the development of novel treatments for neurological and psychiatric conditions.
Used in Sleep Regulation Studies:
2-AMINO-1-(1H-INDOL-3-YL)-ETHANONE is employed in sleep research to investigate the mechanisms of melatonin synthesis and its impact on sleep-wake cycles. This research can contribute to the development of treatments for sleep disorders and the optimization of sleep quality.
Used in Mood Regulation Research:
As a precursor to serotonin, 2-AMINO-1-(1H-INDOL-3-YL)-ETHANONE is used in mood regulation research to explore the biochemical pathways and mechanisms underlying mood disorders. Insights gained from this research can pave the way for the development of new therapeutic strategies for mood-related conditions.

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

Upstream product

• 28755-03-5 3-chloroacetylindole 
• 1236196-94-3 methyl 5-(3-indolyl)oxazole-4-carboxylate 
• 17380-40-4 2-azido-1-(1H-indol-3-yl)ethan-1-one 
• 487-89-8 Indole-3-carboxaldehyde 
• 444108-97-8 2-(1H-indol-3-yl)-2-((trimethylsilyl)oxy)acetonitrile 
• 19611-93-9 2-bromo-1-(1H-indol-3-yl)ethanone 
• 103549-24-2 tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate 
• 19194-62-8 1H-indol-3-yl(oxo)acetonitrile 
• 689232-04-0 N-[2-oxo-2-(3-indolyl)ethyl]carbamic acid tert-butyl ester 

Downstream Products

• 233680-27-8 1-benzenesulfonyl-5-(1H-indol-3-yl)-1H,7H-pyrrolo[3,2-f]indole-4,8-dione 
• 134029-44-0 nortopsentine B 
• 53552-11-7 <2-(1H-indol-3-yl)-2-oxoethyl> ammonium chloride 
• 30256-72-5 8-oxo-N,N-dimethyltryptamine 
• 15879-28-4 1-indol-3-yl-2-methylamino-ethanone 

Relevant academic research and scientific papers

A concise synthesis of indolic enamides: coscinamide A, coscinamide B, and igzamide

A concise synthesis of indolic enamides coscinamide A, coscinamide B, and the brominated tryptamine derivative igzamide is described. Both E- and Z-isomers of these natural compounds were obtained during the thermally assisted dehydration reaction and wer

Reduction of 2,5-bis(3′-indolyl)pyrazines to 2,5-bis(3′- indolyl)piperazines: Synthesis of bisindolylpiperazine marine alkaloids dragmacidin A, B, and C

A concise total synthesis of the bisindole alkaloids drag-macidin A, B and C is described that centers on the preparation and reduction of 2,5-bis(3′-indolyl)pyrazines to 2,5-bis(3′-indolyl)piperazines. Georg Thieme Verlag Stuttgart.

The potential of achiral sponge-derived and synthetic bromoindoles as selective cytotoxins against PANC-1 tumor cells

Our quest to isolate and characterize natural products with in vitro solid tumor selectivity is driven by access to repositories of Indo-Pacific sponge extracts. In this project an extract of a species of Haplosclerida sponge obtained from the US NCI Natural Products Repository displayed, by in vitro disk diffusion assay (DDA) and IC50 determinations, selective cytotoxicity with modest potency to a human pancreatic cancer cell line (PANC-1) relative to the human lymphoblast leukemia cell line (CCRF-CEM). Two brominated indoles, the known 6-bromo conicamin (1) and the new derivative, 6-Br-8-keto-conicamin A (2), were identified and 2 (IC50 1.5 μM for the natural product vs 4.1 μM for the synthetic material) was determined to be responsible for the cytotoxic activity of the extract against the PANC-1 tumor cell line. The new natural product and ten additional analogs were prepared for further SAR testing.

Metabolism of the phytoalexins camalexins, their bioisosteres and analogues in the plant pathogenic fungus Alternaria brassicicola

The metabolism of the phytoalexins camalexin (1), 1-methylcamalexin (10) and 6-methoxycamalexin (11) by Alternaria brassicicola and their antifungal activity is reported. This work establishes that camalexins are slowly biotransformed (ca. six days) to the corresponding indole-3-thiocarboxamides, which are further transformed to the indole-3-carboxylic acids. These metabolites are substantially less inhibitory to A. brassicicola than the parent camalexins, indicating that these enzyme-mediated transformations are detoxifications. In addition, analyses of the metabolism of synthetic isomers and bioisosteres of camalexin (1) indicate that isomers of camalexin in the thiazole ring are not metabolized. Based on these results, the potential intermediates that lead to formation of indole-3-thiocarboxamides are proposed.

Synthesis of 5-(3-indolyl)oxazole natural products. Structure revision of Almazole D

The synthesis and utility of β-oxotryptamine and β-oxytryptophan ester synthons provide a convenient entry to 5-(3-indolyl)oxazole natural products leading to a structure revision of almazole D.

Methods for making bis-heterocyclic alkaloids

Methods for making bis-heterocyclic compounds, especially bis-heterocyclic compounds having five and six-membered heterocyclic linkers are described. Also described are methods for making an alpha amino ketone synthon that enables facile syntheses of bisindole compounds, including topsentins and dragmacidins.

A facile synthesis of dragmacidin B and 2,5-bis(6′-bromo-3′-indolyl)piperazine

(matrix presented) A short synthesis of dragmacidin B (1), 2,5-bis(6′-bromo-3′-indolyl)piperazine (2), and corresponding didebromo analogues 8 and 9 is described. The key steps involve the dimerization of oxotryptamines 4 and 11 to give bis(indolyl)pyrazines 5 and 12, which upon selective reduction and reductive methylation with sodium cyanoborohydride afforded the requisite piperazine natural products.

Synthesis of a bis-pyrrolo-quinone structure analogue to wakayin

The addition of different amines to indole-4,7-quinone is studied. The application of this reaction with indolyl-2-oxoethylamine lead to the preparation of an analogue of wakayin 2.