56363-84-9Relevant academic research and scientific papers
Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air
Bao, Xuefei,Chen, Guoliang,Dong, Jinhua,Du, Fangyu,Li, Hui,Liang, Xinjie,Wu, Ying,Zhang, Yongsheng
supporting information, (2020/08/03)
L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.
Application of quebrachitol in hydrolysis reaction of copper-catalyzed aryl halide
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Paragraph 0045-0047, (2019/07/16)
The invention belongs to the technical field of drug synthesis, and provides application of quebrachitol in a hydrolysis reaction of a copper-catalyzed aryl halide. According to the hydrolysis reaction, copper serves as a catalyst, quebrachitol serves as a ligand, and the hydrolysis reaction is carried out on the aryl halide. The invention further provides a catalytic system of the hydrolysis reaction of the aryl halide. The reaction system comprises the copper catalyst, the quebrachitol, alkali and water, and the system is environmentally friendly and is suitable for industrial application.
Target hopping as a useful tool for the identification of novel EphA2 protein-protein antagonists
Tognolini, Massimiliano,Incerti, Matteo,Pala, Daniele,Russo, Simonetta,Castelli, Riccardo,Hassan-Mohamed, Iftiin,Giorgio, Carmine,Lodola, Alessio
supporting information, p. 67 - 72 (2014/01/17)
Lithocholic acid (LCA), a physiological ligand for the nuclear receptor FXR and the G-protein-coupled receptor TGR5, has been recently described as an antagonist of the EphA2 receptor, a key member of the ephrin signalling system involved in tumour growth. Given the ability of LCA to recognize FXR, TGR5, and EphA2 receptors, we hypothesized that the structural requirements for a small molecule to bind each of these receptors might be similar. We therefore selected a set of commercially available FXR or TGR5 ligands and tested them for their ability to inhibit EphA2 by targeting the EphA2-ephrin-A1 interface. Among the selected compounds, the stilbene carboxylic acid GW4064 was identified as an effective antagonist of EphA2, being able to block EphA2 activation in prostate carcinoma cells, in the micromolar range. This finding proposes the "target hopping" approach as a new effective strategy to discover new protein-protein interaction inhibitors. Target hopping: Given the ability of lithocholic acid to recognize FXR, TGR5 and EphA2 receptors, we hypothesized the structural requirements to bind each of these receptors might be similar. We selected a set of commercially available FXR or TGR5 ligands and tested them for their ability to inhibit EphA2 by targeting the EphA2-ephrin-A1 interface. Moreover, a small panel of GW4064 derivatives was synthesized. Copyright
The site-selective functionalization of halogen-bearing phenols: An exercise in diversity-oriented organometallic synthesis
Marzi, Elena,Schlosser, Manfred
, p. 3393 - 3401 (2007/10/03)
The organometallic approach to diversity-oriented organic synthesis was subjected to a further test, this time in the phenol series. The model compounds selected were 2,3,6-trifluorophenol, the three isomers of (trifluoromethoxy) phenol and the three isomers of chlorophenol. A combination of optionally site selective metalations and protective group-controlled metalations enabled the selective generation of several isomeric intermediates in each case and their subsequent conversion into functionalized derivatives, in particular hydroxybenzoic acids.
Optimization of alkylidene hydrazide based human glucagon receptor antagonists. Discovery of the highly potent and orally available 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1h-indol-4ylmethylene]hydrazide
Madsen, Peter,Ling, Anthony,Plewe, Michael,Sams, Christian K.,Knudsen, Lotte B.,Sidelmann, Ulla G.,Ynddal, Lars,Brand, Christian L.,Andersen, Birgitte,Murphy, Douglas,Teng, Min,Truesdale, Larry,Kiel, Dan,May, John,Kuki, Atsuo,Shi, Shenghua,Johnson, Michael D.,Teston, Kimberly Ann,Feng, Jun,Lakis, James,Anderes, Kenna,Gregor, Vlad,Lau, Jesper
, p. 5755 - 5775 (2007/10/03)
Highly potent human glucagon receptor (hGluR) antagonists have been prepared employing both medicinal chemistry and targeted libraries based on modification of the core (proximal) dimethoxyphenyl group, the benzyl ether linkage, as well as the (distal) benzylic aryl group of the lead 2, 3-cyano-4-hydroxybenzoic acid (3,5-dimethoxy-4-isopropylbenzyloxybenzylidene)hydrazide. Electron-rich proximal aryl moieties such as mono- and dimethoxy benzenes, naphthalenes, and indoles were found to be active. The SAR was found to be quite insensitive regarding the linkage to the distal aryl group, since long and short as well as polar and apolar linkers gave highly potent compounds. The presence of a distal aryl group was not crucial for obtaining high binding affinity to the hGluR. In many cases, however, the affinity could be further optimized with substituted distal aryl groups. Representative compounds have been tested for in vitro metabolism, and structure - metabolism relationships are described. These efforts lead to the discovery of 74, NNC 25-2504, 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide, with low in vitro metabolic turnover. 74 was a highly potent noncompetitive antagonist of the human glucagon receptor (IC50 = 2.3 nM, KB = 760 pM) and of the isolated rat receptor (IC50 = 430 pM, KB = 380 pM). Glucagonstimulated glucose production from isolated primary rat hepatocytes was inhibited competitively by 74 (Ki = 14 nM). This compound was orally available in dogs (Fpo = 15%) and was active in a glucagon-challenged rat model of hyperglucagonemia and hyperglycemia.
Sulfonamide compounds and medicinal use thereof
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Page column 109, (2010/02/04)
A sulfonamide compound of the formula (I):R 1 --SO 2 NHCO--A--R 2 (I)wherein R 1 is alkyl, alkenyl, alkynyl and the like; A is an optionally substituted heteropolycyclic group except benzimidazolyl, indolyl, 4,7-dihydrobenzimidazolyl and 2,3-dihydrobenzoxazinyl; X is alkylene, oxa, oxa(lower)alkylene and the like; and R 2 is optionally substituted aryl, substituted biphenylyl and the like, a salt thereof and a pharmaceutical composition comprising the same. The sulfonamide compound is effective for the diseases treatable based on their blood sugar level-depressing activity, cGMP-PDE (especially PDE-V)-inhibiting activity, smooth muscle relaxing activity, bronchodilating activity, vasodilating activity, smooth muscle cell suppressing activity, and antiallergic activity.
IMIDAZOLE COMPOUNDS AND MEDICINAL USE THEREOF
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, (2008/06/13)
Imidazole compounds represented by general formula (I): wherein each symbol is as defined in the specification, and salts thereof, and a pharmaceutical composition containing same are provided. These compounds are useful in treating the diseases curable based on a hypoglycemic action, and the diseases curable based on a cGMP-PDE inhibitory action, a smooth muscle relaxing action, a bronchodilating action, a vasodilating action, a smooth muscle cell inhibitory action and an allergy inhibitory action.
Mesomorphic compound having β-hydroxycarboxyl group as chiral source and liquid crystal composition
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, (2008/06/13)
Disclosed is a mesomorphic compound having a β-hydroxycarboxyl group as the chiral source, which is represented by the formula: STR1 wherein m and n are integers of from 1 to 18, X1 and X2 independently represent fluorine, chlorine or hydrogen, Y represents STR2 or --O--, Z represents a direct bond, STR3 --CH hd 2O-- or --OCH2 --, and * indicates the asymmetric carbon. The mesomorphic compound is valuable as a ferroelectric liquid crystal or an additive to a ferroelectric liquid crystal or to a compound showing the SmC phase and having no chiral group.
Mesomorphic Phenyl Benzoate and 1,3-Dioxane Derivatives Bearing Terminal Vinyl Group
Kamogawa, Hiroyoshi,Hirose, Tomoki,Nanasawa, Masato
, p. 3517 - 3518 (2007/10/02)
4-Alkylphenyl 2-chloro-4-(4-vinylbenzoyloxy) benzoates and 2-phenyl-1,3-dioxane derivatives with terminal vinyl groups were synthesized.Most of the novel compounds obtained possess characteristic mesomorphic ranges.
