91444-33-6Relevant academic research and scientific papers
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
, p. 1096 - 1102 (2021/01/26)
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
Thermal and spectroscopic studies of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles as non-competitive antagonists of GluK1/GluK2 receptors
Bartyzel, Agata,Kaczor, Agnieszka A.,G?uchowska, Halina,Pitucha, Monika,Wróbel, Tomasz M.,Matosiuk, Dariusz
, p. 935 - 944 (2018/03/21)
This paper reports the thermal stability and thermal degradation of six derivatives of indole by means of TG-DSC (in air) and TG-FTIR (in nitrogen) techniques. The compounds were also characterized by infrared spectroscopy. In addition, IR spectra were ca
Oxygenophilic Lewis Acid Promoted Synthesis of 2-Arylindoles from Anilines and Cyanoepoxides in Alcohol
Xu, Chuangchuang,Xu, Jiaxi
, p. 14733 - 14742 (2018/11/27)
A convenient synthetic method to indoles from anilines and cyanoepoxides was developed under the catalysis of BF3·OEt2 or AlCl3 in alcohols. The reaction involves a tandem reaction of the regiospecific ring-opening of cyanoepoxides with anilines, elimination of cyanide, intramolecular aromatic electrophilic substitution, and water elimination. The Lewis acid generated protic acid is an efficient catalyst. The method features readily accessible starting materials, wide substrate scope, transition-metal-free environment, and regiospecificity in the ring-opening of cyanoepoxides.
Structural studies, homology modeling and molecular docking of novel non-competitive antagonists of GluK1/GluK2 receptors
Kaczor, Agnieszka A.,Karczmarzyk, Zbigniew,Fruziński, Andrzej,Pihlaja, Kalevi,Sinkkonen, Jari,Wiin?maki, Kirsti,Kronbach, Christiane,Unverferth, Klaus,Poso, Antti,Matosiuk, Dariusz
, p. 787 - 795 (2014/01/23)
Non-competitive ligands of kainate receptors have focused significant attention as medicinal compounds because they seem to be better tolerated than competitive antagonists and uncompetitive blocker of these receptors. Here we present structural studies (
Novel non-competitive antagonists of kainate GluK1/GluK2 receptors
Kaczor, Agnieszka Anna,Kronbach, Christiane,Unverferth, Klaus,Pihlaja, Kalevi,Wiinam?ki, Kirsti,Sinkkonen, Jari,Kijkowska-Murak, Urszula,Wróbel, Tomasz,Stacha, Tomasz,Matosiuk, Dariusz
, p. 891 - 898 (2013/02/22)
A series of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles is synthesized by Fisher or Bischler method, followed by alkylation with an appropriate alkyl or aryl halide. Two compounds exhibit non-competitive antagonism towards GluK1 and six - towards GluK2 receptor. The values of IC 50 are in micromolar range. The investigated compounds belong to the most active GluK1 non-competitive inhibitors and are the first known negative allosteric modulators of GluK2 receptor. The observed pattern of activity is rationalized by molecular modelling, in particular by construction of the pharmacophore model.
Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling
Fuerstner, Alois,Jumbam, Denis N.,Seidel, Guenter
, p. 1125 - 1130 (2007/10/02)
Highly reactive titanium on graphite is used to reductively cyclize electron-rich acylamino carbonyl compounds 7, 8, 12, 14, and 16 to the corresponding indole derivatives 9, 10, 13, 15, and 17.Compound 9b is a known precursor of the mammary tumor-inhibiting compound zindoxifene (2).The other products are new analogues of this anticancer drug, exhibiting the substitution pattern previously recognized to be essential for high pharmacological activity. - Key Words: Indoles, 2-aryl- / Titanium graphite / Zindoxifene / Tumor-growth inhibitors / Alkylidenation, intramolecular
2-Phenylindoles. Relationship between Structure, Estrogen Receptor Affinity, and Mammary Tumor Inhibiting Activity in the Rat
Angerer, Erwin von,Prekajac, Jelica,Strohmeier, Josef
, p. 1439 - 1447 (2007/10/02)
A number of 2-phenylindole derivatives with one hydroxy group in the meta or para position of the phenyl ring and a second one in position 5, 6, or 7 of the indole nucleus were synthesized.In addition, different alkyl groups were introduced into positions
