76834-78-1Relevant academic research and scientific papers
Anhydrous Hydrogen Iodide-Mediated Reductive Indolization of in Situ-Generated Cyclopropyl Hydrazones
Yasui, Motohiro,Fujioka, Hiroki,Takeda, Norihiko,Ueda, Masafumi
, p. 43 - 47 (2021/12/17)
Fischer-type indolization of N-aryl-C-cyclopropyl hydrazones generated in situ followed by chemoselective reduction using tert-butyl iodide as an anhydrous HI generator was developed. This protocol provides indoles bearing carboxylic acid derivative units. A series of control experiments indicated the HI-mediated formation and reduction of spirocyclopropyl indolenines. Anhydrous HI functions as a Br?nsted acid as well as a reducing agent, facilitating the successful conversion of unstable reaction intermediates and iodinated mixtures in equilibrium.
Radical-Mediated Dearomatization of Indoles with Sulfinate Reagents for the Synthesis of Fluorinated Spirocyclic Indolines
Ryzhakov, Dmytro,Jarret, Maxime,Guillot, Régis,Kouklovsky, Cyrille,Vincent, Guillaume
, p. 6336 - 6339 (2017/12/08)
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.
Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor
James, Michael J.,O'Brien, Peter,Taylor, Richard J. K.,Unsworth, William P.
supporting information, p. 9671 - 9675 (2016/08/10)
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.
Novel N -Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential
De La Fuente Revenga, Mario,Fernández-Sáez, Nerea,Herrera-Arozamena, Clara,Morales-García, José A.,Alonso-Gil, Sandra,Pérez-Castillo, Ana,Caignard, Daniel-Henri,Rivara, Silvia,Rodríguez-Franco, María Isabel
, p. 4998 - 5014 (2015/07/02)
Herein we present a new family of melatonin-based compounds, in which the acetamido group of melatonin has been bioisosterically replaced by a series of reversed amides and azoles, such as oxazole, 1,2,4-oxadiazole, and 1,3,4-oxadiazole, as well as other related five-membered heterocycles, namely, 1,3,4-oxadiazol(thio)ones, 1,3,4-triazol(thio)ones, and an 1,3,4-thiadiazole. New compounds were fully characterized at melatonin receptors (MT1R and MT2R), and results were rationalized by superimposition studies of their structures to the bioactive conformation of melatonin. We also found that several of these melatonin-based compounds promoted differentiation of rat neural stem cells to a neuronal phenotype in vitro, in some cases to a higher extent than melatonin. This unique profile constitutes the starting point for further pharmacological studies to assess the mechanistic pathways and the relevance of neurogenesis induced by melatonin-related structures.
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.
Reactions of Organic Anions, 147.- Simple and General Synthesis of Hydroxy- and Methoxyindoles via Vicarious Nucleophilic Substitution of Hydrogen
Makosza, Mieczyslaw,Danikiewicz, Witold,Wojciechowski, Krzysztof
, p. 203 - 208 (2007/10/02)
A simple synthesis of 4-, 5-, 6-, and 7-hydroxy- and -methoxyindoles via cyanoalkylation of O-protected nitrophenols by vicarious nucleophilic substitution of hydrogen, followed by catalytic hydrogenation of the (2-nitroaryl)acetonitriles obtained is described.
