3471-31-6

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxyindole-3-acetic acid is used as a reactant for the preparation of aryloxybenzothiazoles, which act as inhibitors of NO production, helping in the development of treatments for various inflammatory and cardiovascular conditions.
5-Methoxyindole-3-acetic acid is also used as a reactant for the preparation of transcription inhibitors of novel Gli1, which have potential applications as antitumor agents, targeting specific cancer-related pathways.
Used in Neuropharmacology:
5-Methoxyindole-3-acetic acid is used as a reactant for the preparation of indole derivatives, which function as NR2B/NMDA receptor antagonists. These compounds have potential applications in the treatment of neurological disorders, such as Alzheimer's disease and schizophrenia.
Used in Anti-inflammatory Drug Development:
5-Methoxyindole-3-acetic acid is used as a reactant for the preparation of indolyl esters and amides related to indomethacin, which are selective COX-2 inhibitors. These compounds have potential applications in the development of anti-inflammatory drugs with reduced side effects.
Used in Immunology:
5-Methoxyindole-3-acetic acid is used as a reactant for the preparation of quinoline salicylic acid series of P-selectin antagonists. These compounds have potential applications in the treatment of inflammatory and autoimmune diseases by modulating cell adhesion and leukocyte recruitment.
Used in Prostaglandin Research:
5-Methoxyindole-3-acetic acid is used as a reactant for the preparation of prostaglandin D2 receptor antagonists. These compounds have potential applications in the treatment of allergic diseases, such as asthma and allergic rhinitis, by modulating the effects of prostaglandin D2.
Used in Plant Physiology Research:
5-Methoxyindole-3-acetic acid is used as a chemical reagent in the analysis of the physiological properties of auxins, which are plant hormones that regulate growth and development. This application aids in understanding the mechanisms of plant growth and the development of new agricultural technologies.

InChI:InChI=1/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)/p-1

Upstream product

• 2436-17-1 5-methoxyindole-3-acetonitrile 
• 57000-49-4 (5-methoxy-1H-indol-3-yl)acetic acid ethyl ester 
• 23304-48-5 (5-methoxy-1H-indol-3-yl)acetic acid methyl ester 
• 2426-19-9 (5-methoxy-1H-indol-3-yl)oxoacetyl chloride 
• 99988-56-4 methyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate 
• 104-94-9 4-methoxy-aniline 
• 3471-31-6 5-methoxy-1H-indole-3-acetic acid 
• 15478-18-9 (5-hydroxy-1H-indol-3-yl)acetic acid methyl ester 
• 54-16-0 5-Hydroxyindole-3-acetic acid 
• 14827-68-0 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetic acid 
• 858232-58-3 3-(carboxymethyl)-5-methoxy-1H-indole-2-carboxylic acid 
• 72963-98-5 ethyl 3-(2-ethoxy-2-oxoethyl)-5-methoxy-1H-indole-2-carboxylate 
• 1006-94-6 5-methoxylindole 

Downstream Products

• 54-16-0 5-Hydroxyindole-3-acetic acid 
• 57000-49-4 (5-methoxy-1H-indol-3-yl)acetic acid ethyl ester 
• 55887-55-3 N,O-Bis(trimethylsilyl)-5-methoxyindolyl-3-essigsaeureester 
• 185064-27-1 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid phenylmethyl ester 
• 23304-48-5 (5-methoxy-1H-indol-3-yl)acetic acid methyl ester 
• 924635-04-1 2-(1-(benzyloxycarbonyl)-5-methoxy-1H-indol-3-yl)acetic acid 
• 1067133-53-2 C₂₄H₂₈O₄N₂ 
• 712-09-4 5-methoxytryptophol 
• 487-93-4 bufotenin 
• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 

Relevant academic research and scientific papers

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst

Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.

Agent for Preventing or Ameliorating Hearing Impairment

It is to provide an agent for preventing or improving hearing loss, which comprises a low molecular compound which can be produced relatively easily and inexpensively as an active ingredient. One or more compounds selected from the group consisting of compounds represented by the following formulas (I0), (II), and (III) and a pharmaceutically acceptable salt of the compounds when R3 is OH are used as an agent for preventing or improving hearing loss.

A substituted indole -3 - acetic acid synthesis method (by machine translation)

The present invention provides a substituted indole - 3 - acetic acid synthesis method, comprises the following steps: (1) in order to replace the indole as the starting material, with the acylation reagent under the action of catalyst through the tutor - acylation to obtain the 1, 3 - diacetyl substituted indole; (2) intermediate 1, 3 - diacetyl substituted indole does not need refining, directly with the morpholine and sulfur by the Willgerodt - Kindler rearrangement reaction, the inorganic under the catalysis of alkali hydrolysis, acidified to obtain substituted indole - 3 - acetic acid. (by machine translation)

Aryl [a] indole [2,3 - the g] and quinolizine compound, preparation method thereof, pharmaceutical compositions and uses thereof

The invention relates to an aryl [a] indole [2,3-g] quinolizine compound as well as a preparation method, a pharmaceutical composition and application thereof, and particularly relates to a aryl [a] indole [2,3-g] quinolizine compound with a novel structure as shown in a general formula (I) and a derivative, a preparation method and a pharmaceutical composition thereof and application of the aryl [a] indole [2,3-g] quinolizine compound in preparation of a drug for treating diseases related to alpha 1-adrenoreceptor and urinary system diseases, such as benign prostatic hyperplasia, uroschesis and bladder outlet obstruction, especially.

Erythropoietin Expression Promoter

The present invention provides an erythropoietin expression-enhancing agent that can cancel the suppression of erythropoietin production or promote erythropoietin production, and a therapeutic or preventive drug for anemia, a liver function-improving agent, an ischemic injury-improving agent, a renal protective agent, and an insulin secretagogue comprising the erythropoietin expression-enhancing agent. The erythropoietin expression-enhancing agent of the present invention comprises one or more compounds selected from the group consisting of compounds represented by the following general formulas (I), (II), and (III) and pharmaceutically acceptable salts thereof when R3 is OH.

Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade

An enantioselective arylation-cyclization cascade has been accomplished using a combination of diaryliodonium salts and asymmetric copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction of pyrroloindolines, an important alkaloid structural motif that is commonly found among biologically active natural products.

Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana

Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-β-d-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these amino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis.

Design, synthesis, and melatoninergic activity of new azido- and isothiocyanato-substituted indoles

To develop irreversibly binding ligands for the melatonin receptor(s) as tools for tracing the primary melatonin binding site, we report on the design and synthesis of new melatoninergic azido- and isothiocyanato-substituted indoles. All active compounds were partial agonists or antagonists in the Xenopus melanophore assay, the most potent being the 5-OMe C3-substituted azido 45 and isothiocyanato 46 analogues.

Aromatic bromination versus oxidation of indolylmalonates by bromine

The reactions of 5-substituted indolylmalonates (2a-e), carrying an electron-withdrawing group at the N(1) position, with bromine in CCl4 or AcOH are reported. These substrates undergo oxidation in competition with the well-known aromatic bromination. Under the two sets of conditions, with parent indolylmalonate (2a), chemospecific oxidation is observed, whereas with 5-hydroxyindolylmalonate (2c), bromination at the 4- and 6-position is the dominating reaction. Investigation of the products composition of several 5-substituted indolylmalonates revealed the following trend: with a 5-substituted electron-withdrawing group like fluorine, the indolylmalonate undergoes oxidation rather than bromination. In contrast, with a 5-substituted electron-donating group, like a hydroxyl group, the ring bromination occurs preferentially over the oxidation. When the 5-substituent is an alkoxyl group, a significant amount of brominated-oxidized products is obtained. Monitoring the oxidation reaction by mass spectrometry allowed the characterization of the 2-bromoindolylidenemalonate intermediate. A bromonium ion is considered as possible pathway in the formation of this intermediate. The conformation of unsymmetrical methoxyl and benzyloxyl substituents was determined from 1H NMR spectra, single-crystal X-ray diffraction and ab initio calculations.

New N-(pyridin-4-yl)-(indol-3-yl)acetamides and propanamides as antiallergic agents

A series of new N-(pyridin-4-yl)-(indol-3-yl)alkylamides 44-84 has been prepared in the search of novel antiallergic compounds. Synthesis of the desired ethyl (2-methyindol-3-yl)acetates 1-4 was achieved by indolization under Fischer conditions; Japp-Klingemann method followed by 2- decarboxylation afforded the ethyl (indol-3-yl)alkanoates 17-25. Amidification was successfully carried out by condensation of the corresponding acids or their N-aryl(methyl) derivatives with 4-aminopyridine promoted by 2-chloro-1-methylpyridinium iodide. Efforts to improve the antiallergic potency of the title series by variation of the indole substituents (R1, R2, R) and the length of the alkanoic chain (n = 1, 2, 3) led to the selection of N-(pyridin-4-yl)-[1-(4-fluorobenzyl)indol-3- yl]acetamide 45, out of 41 compounds. This amide was 406-fold more potent than astemizole in the ovalbumin-induced histamine release assay, using guinea pig peritoneal mast cells, with an IC50 = 0.016 μM. Its inhibitory activity in IL-4 production test from Th-2 cells was identical to that of the reference histamine antagonist (IC50 = 8.0 μM) and twice higher in IL-5 assay: IC50 = 1.5 and 3.3 μM, respectively. In vivo antiallergic activity evaluation confirmed efficiency of 45 in sensitized guinea pig late phase eosinophilia inhibition, after parenteral and oral administration at 5 and 30 mg/kg, respectively. Its efficiency in inhibition of microvascular permeability was assessed in two rhinitis models; ovalbumin and capsaicin- induced rhinorrhea could be prevented after topical application of submicromolar concentrations of 45 (IC50 = 0.25 and 0.30 μM); and it also exerted significant inhibitory effect in the first test after iv and oral administration, with ID50 = 0.005 and 0.46 mg/kg.