61675-19-2

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-3-(2-NITROVINYL)-INDOL is used as a reactant for the preparation of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These inhibitors play a crucial role in regulating cellular processes such as inflammation, cell growth, and apoptosis, making them important targets for the development of therapeutic agents.
Used in Chemical Industry:
5-METHOXY-3-(2-NITROVINYL)-INDOL is used as a reactant for the synthesis of indole lipoic acid derivatives. These derivatives exhibit antioxidant properties and are effective against lipid peroxidation, a process that can lead to cellular damage and contribute to various diseases, including cardiovascular and neurodegenerative disorders.
Used in Biotechnology Industry:
5-METHOXY-3-(2-NITROVINYL)-INDOL is used as a reactant for the preparation of indole ethylamine derivatives. These derivatives have been found to act as melatonin analogs, which are important for regulating sleep-wake cycles, mood, and other physiological processes. The development of melatonin analogs can be useful in the treatment of sleep disorders and other conditions related to the circadian rhythm.

InChI:InChI=1/C11H10N2O3/c1-16-9-2-3-11-10(6-9)8(7-12-11)4-5-13(14)15/h2-7,12H,1H3/b5-4-

Upstream product

• 10601-19-1 5-methoxyindole-3-carboxaldehyde 
• 75-52-5 nitromethane 
• 1006-94-6 5-methoxylindole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 73430-27-0 (E)-N,N-dimethyl-2-nitroethenamine 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 1554471-88-3 2-bromo-4-(1-(5-methoxy-1H-indol-3-yl)-2-nitroethyl)aniline 
• 847851-60-9 C₂₂H₂₆N₂O₂ 
• 1631136-28-1 C₂₉H₃₂N₂O₂ 
• 1020701-51-2 N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide 
• 67199-10-4 methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 947767-16-0 C₁₈H₂₀N₂O 
• 20731-70-8 5-methoxy-α-methyltryptamine 
• 3589-72-8 6-methoxyharman 
• 66012-82-6 N-Propionyl-5-methoxytryptamine 

Relevant academic research and scientific papers

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.

Method for synthesizing melatonin intermediate by taking methoxyphenamine as raw material

The invention belongs to the technical field of compound synthesis, and aims to solve the problem that expensive reducing agents are needed in the present method for synthesizing melatonin, and the cost is high. The invention provides a method for synthesizing melatonin intermediate by taking methoxyphenamine as a raw material, and the like. Pt / Al with supported catalyst by taking methoxyaniline and ethylene glycol as raw materials2 O3 One-step hydrothermal method synthesizes 5 - methoxyindole and then obtains melatonin precursor 3 methoxytryptamine by 5 -step hydrothermal reaction. 5 - Methoxyindole is firstly synthesized by taking ethylene glycol and paramethoxyaniline as raw materials, then 3 methoxytryptamine is obtained through 5 - steps, and the total yield of the reaction is 14.0%. final synthesis of melatonin. A new melatonin synthesis route is designed, and the melatonin precursor 5 - methoxytryptamine is synthesized by using a raw material aniline derivative and ethylene glycol which are simple in application structure and low in cost.

Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow

A metal-free, phosphine-catalyzed intramolecular “umpolung Michael addition” on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope of five- and six-membered spiroindol(en)ines in moderate to excellent yields in batch as well as under continuous-flow conditions. Triphenylphosphine-catalyzed nucleophilic activation of alkynes allows the exclusive formation of exo-product under mild reaction conditions.

Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Indole Derivatives: Access to 1-(Trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indole and β-Carboline Derivatives

A visible-light-induced trifluoromethylation of isonitrile-substituted indole derivatives has been developed from the reaction of isonitrile-substituted indoles with Togni II reagent, affording 1-(trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indoles in mo

An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives

An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.

Revision of the Structure and Total Synthesis of Topsentin C

An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.

Chiral anion phase transfer of aryldiazonium cations: An enantioselective synthesis of C3-diazenated pyrroloindolines

Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air- and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core. Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99% yield and 96% ee (MTBE=methyl tert-butyl ether).

Synthesis and structureactivity relationship of novel conformationally restricted analogues of serotonin as 5-HT6 receptor ligands

5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structureactivity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the Ki of 23.4 and 20.5nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

First total synthesis of marine alkaloid hyrtiosulawesine

Hyrtiosulawesine was isolated from Indonesian specimens of the marine sponges Hyrtios erectus and H. reticulatu in 2002. We report here the first total synthesis of hyrtiosulawesine using an efficient and convenient synthetic strategy which could be widely used in the synthesis of other β-caboline compounds. All structures of new compounds were confirmed by 1H NMR, 13C NMR and HRMS.

INDOLE COMPOUNDS, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein: R1 represents an alkyl, cycloalkyl or cycloalkylalkyl group,R2 and R3, together with the nitrogen atom carrying them, form a heterocycle having from 5 to 8 ring members,and n represents from 2 to 6. Medicinal products containing the same which are useful in treating disorders of the to melatoninergic system.