651326-28-2Relevant academic research and scientific papers
Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives
Li, Shan,Liang, Jian,Liu, Xiaofeng,Xian, Liqing,Du, Mingxu
, p. 1041 - 1053 (2020/10/02)
A simple and efficient method of iodine-mediated aminohalogenation-oxidation of fluorinated N’-propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes was developed. This method showed good functional group compatibility and wide substrat
Bi(iii)-catalyzed aminooxygenation of propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes and their decarbonylations
Li, Shan,Li, Yajun,Feng, Bin,Liang, Jian,You, Geyun,Liu, Xiaofeng,Xian, Liqing
, p. 6400 - 6403 (2020/06/21)
The first example of main group metal Bi(iii)-catalyzed aminooxygenation of fluorinated propargyl amidines was developed to produce 2-fluoroalkyl imidazole-5-carbaldehydes in moderate to excellent yields, in which phenol played a critical role and could be recovered and recycled. In the presence of KOt-Bu, an unconventional decarbonylation occurred on the 2-fluoroalkyl imidazole-5-carbaldehydes.
Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes
Chu, Lingling,Qing, Feng-Ling
supporting information; experimental part, p. 1298 - 1304 (2012/02/16)
This article describes the copper-catalyzed oxidative trifluoromethylation of heteroarenes and highly electron-deficient arenes with CF 3SiMe3 through direct C-H activation. In the presence of catalyst Cu(OAc)2, ligand 1,10-phenanthroline and cobases tert-BuONa/NaOAc, oxidative trifluoromethylation of 1,3,4-oxadiazoles with CF3SiMe3 proceeded smoothly using either air or di-tert-butyl peroxide as an oxidant to give the corresponding trifluoromethylated 1,3,4-oxadiazoles in high yields. Di-tert-butyl peroxide was chosen as the suitable oxidant for oxidative trifluoromethylation of 1,3-azoles and perfluoroarenes. Cu(OH)2 and Ag2CO3 were the best catalyst and oxidant for direct oxidative trifluoromethyaltion of indoles. The optimum reaction conditions enable oxidative trifluoromethylation of a range of heteroarenes that bear numerous functional groups. The prepared trifluoromethylated heteroarenes are of importance in the areas of pharmaceuticals and agrochemicals. The preliminary mechanistic studies of these oxidative trifluoromethylations are also reported.
Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities
Sun, Xicheng,Qiu, Jian,Strong, Sarah A.,Green, Louis S.,Wasley, Jan W.F.,Blonder, Joan P.,Colagiovanni, Dorothy B.,Mutka, Sarah C.,Stout, Adam M.,Richards, Jane P.,Rosenthal, Gary J.
, p. 5849 - 5853 (2011/10/19)
The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.
Novel imidazole compounds as a new series of potent, orally active inhibitors of 5-lipoxygenase
Mano, Takashi,Stevens, Rodney W.,Ando, Kazuo,Nakao, Kazunari,Okumura, Yoshiyuki,Sakakibara, Minoru,Okumura, Takako,Tamura, Tetsuya,Miyamoto, Kimitaka
, p. 3879 - 3887 (2007/10/03)
Replacement of the dihydroquinolinone pharmacophore of Zeneca's ZD2138 by ionizable imidazolylphenyl moiety has lead to the discovery of a novel series of potent and orally active 5-lipoxygenase (5-LO) inhibitors. The synthesis and structure-activity relationship (SAR) of this series of compounds are described herein.
