39547-16-5

Usage

InChI:InChI=1/C12H13NO3/c1-16-9-3-4-11-10(6-9)8(7-13-11)2-5-12(14)15/h3-4,6-7,13H,2,5H2,1H3,(H,14,15)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 1006-94-6 5-methoxylindole 
• 79-10-7 acrylic acid 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 90858-80-3 ethyl 3-(3-ethoxy-3-oxopropyl)-5-methoxy-1H-indole-2-carboxylate 
• 100394-23-8 3-(2-carboxyethyl)-5-methoxy-1H-indole-2-carboxylic acid 
• 474640-46-5 4-ethoxythiocarbonylsulfanyl-5-[methanesulfonyl-(4-methoxy-phenyl)-amino]-pentanoic acid ethyl ester 
• 23004-83-3 N-(4-methoxyphenyl)-N-(prop-2-en-1-yl)methanesulfonamide 
• 474640-47-6 3-(1-methanesulfonyl-5-methoxy-2,3-dihydro-1H-indol-3-yl)-propionic acid ethyl ester 
• 76834-78-1 ethyl 3-(5-Methoxy-1H-indol-3-yl)propionate 

Downstream Products

• 76834-78-1 ethyl 3-(5-Methoxy-1H-indol-3-yl)propionate 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 

Relevant academic research and scientific papers

Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

Indolyl α-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of RhII, PdII, and CuII, as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.

Hypervalent Iodine-Mediated Cyclization of Homotryptamine Derivatives

A facile and efficient cyclization of homotryptamines and their derivatives has been established for the construction of 4a-chlorotetrahydropyrido[2,3-b]indoles and 3,3-spirocyclic 3H-indoles using hypervalent iodine (1-chloro-1,2-benziodoxol-3-one) under mild conditions. The broad substrate scope and successful gram-scale experiment grant this metal-free transformation great potential for further application.

Radical-Mediated Dearomatization of Indoles with Sulfinate Reagents for the Synthesis of Fluorinated Spirocyclic Indolines

The dearomative introduction of trifluoromethyl and 1,1-difluoroethyl radicals, generated from their corresponding sulfinate salts, into the C2 position of indole derivatives allows the diastereoselective synthesis of three-dimensional 3,3-spirocyclic indolines over C-H functionalized indoles.

Sodium Iodide/Hydrogen Peroxide-Mediated Oxidation/Lactonization for the Construction of Spirocyclic Oxindole-Lactones

The sodium iodide/hydrogen peroxide-mediated oxidation/lactonization of indolepropionic acids was achieved, affording the corresponding spirocyclic oxindole-lactones in moderate to high yields. This metal-free procedure features mild reaction conditions, non-toxicity and easy handling, with hydrogen peroxide (H2O2) as a clean oxidant. (Figure presented.).

PPAR ACTIVE COMPOUNDS

Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

A convergent approach to 2-substituted-5-methoxyindoles. Application to the synthesis of melatonin

A convergent, radical based synthesis of 5-methoxyindoles including melatonin is described.

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.