443-73-2Relevant articles and documents
A substituted indole -3 - acetic acid synthesis method (by machine translation)
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Paragraph 0074, (2017/05/02)
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)
Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade
Zhu, Shaolin,MacMillan, David W. C.
supporting information; experimental part, p. 10815 - 10818 (2012/08/07)
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.
New N-(pyridin-4-yl)-(indol-3-yl)acetamides and propanamides as antiallergic agents
Menciu, Cecilia,Duflos, Muriel,Fouchard, Fabienne,Le Baut, Guillaume,Emig, Peter,Achterrath, Ute,Szelenyi, Istvan,Nickel, Bernd,Schmidt, Jürgen,Kutscher, Bernhard,Günther, Eckhardt
, p. 638 - 648 (2007/10/03)
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.
