5458-69-5Relevant articles and documents
Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins
Yang, Lu,Zhu, Jiang,Xie, Fukai,Peng, Xiaoshi,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
, p. 1053 - 1060 (2019/09/06)
A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.
Design, synthesis, and biological evaluation of some novel indolizine derivatives as dual cyclooxygenase and lipoxygenase inhibitor for anti-inflammatory activity
Shrivastava, Sushant K.,Srivastava, Pavan,Bandresh, Robin,Tripathi, Prabhash Nath,Tripathi, Avanish
, p. 4424 - 4432 (2017/07/22)
Some novel indolizine derivatives were synthesized by bioisosteric modification of imidazo[1,2-a]pyridine for anti-inflammatory activity. The physicochemical characterization and structure of compounds were elucidated by state of the art spectroscopic technique. Induced fit docking was performed for initial screening to elucidate the interactions with corresponding amino acids of cyclooxygenase (COX-1, COX-2) and lipoxygenase (LOX) enzymes. The target compounds 53–60 were then evaluated against in vivo carrageenan and arachidonic acid induced rat paw edema models for anti-inflammatory activity. Amongst all the synthesized derivatives, compound 56 showed the significant anti-inflammatory activity in both rat paw edema models with very less ulcerogenic liability in comparison to standard diclofenac, celecoxib, and zileuton. The compounds 56 was further assessed to observe in vitro enzyme inhibition assay on both cyclooxygenase and lipoxygenase enzyme where it showed a preferential and selective non-competitive enzyme inhibition towards the COX-2 (IC50?=?14.91?μM, Ki?=?0.72?μM) over COX-1 (IC50?>?50?μM) and a significant non-competitive inhibition of soybean lipoxygenase enzyme (IC50?=?13.09?μM, Ki?=?0.92?μM). Thus, in silico, in vivo, and in vitro findings suggested that the synthesized indolizine compound 56 has a dual COX-2 and LOX inhibition characteristic and parallel in vivo anti-inflammatory activity in comparison to the standard drugs.
Compounds and methods for treating cancer by inhibiting the urokinase receptor
-
Page/Page column 53; 55; 56; 59, (2017/09/15)
Compounds and methods for treating or preventing cancer associated with binding to the urokinase receptor are provided. Biological processes affected by the compounds include cell migration, cell growth, cell adhesion, angiogenesis, cancer cell invasion, apoptosis, tumor formation, tumor progression, metastasis, degradation of the extracellular matrix, pericellular proteolysis, activation of plasminogen, changes in the levels of an extracellular protease, and changes in the levels of a VEGF receptor.
Nickel(ii)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine imines with alkylidene malonates
Li, Jiangting,Lian, Xiangjin,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 5134 - 5140 (2013/07/05)
We demonstrated an asymmetric 1,3-dipolar cycloaddition of azomethine betaines with alkylidene malonates by using a chiral N,N'-dioxide- NiII complex as a catalyst. Both aromatic- and aliphatic-substituted alkylidene malonates were found to be suitable for the reaction. A range of transpyrazolone derivatives was exclusively obtained with excellent yields (up to 99% yield) and good enantioselectivities (up to 97% ee) under mild reaction conditions. The reaction could be carried out on a gram scale with the good results being maintained. Control experiments were performed to elucidate the specific diastereoselectivity of the reaction. The formation of single trans isomers was dominated by secondary orbital interactions between the ester groups of the dipolarophile and the azomethine imine. On the basis of the experimental results and previous reports, a possible catalytic model was assumed.
Chiral-Zn(NTf2)2-complex-catalyzed diastereo- and enantioselective direct conjugate addition of arylacetonitriles to alkylidene malonates
Yao, Jingjing,Liu, Xiaohua,He, Peng,Zhu, Yin,Lian, Xiangjin,Lin, Lili,Feng, Xiaoming
supporting information, p. 16424 - 16430 (2013/12/04)
Chiral N,N′-dioxide/Zn(NTf2)2 complexes were demonstrated to be highly effective in the direct asymmetric conjugate addition of arylacetonitriles to alkylidene malonates under mild conditions. A wide range of substrates were tolerated to afford their corresponding products in moderate-to-good yields with high diastereoselectivities (82:18->99:1 d.r.) and enantioselectivities (81-99 % ee). The reactions performed well, owing to the high Lewis acidity of the metal triflimidate and a ligand-acceleration effect. The N,N′-dioxide also benefited the deprotonation process as a Bronsted base. The catalytic reaction could be performed on the gram-scale with retention of yield, diastereoselectivity, and enantioselectivity. The products that contained functional groups were ready for further manipulation. In addition, a possible catalytic model was proposed to explain the origin of the asymmetric induction. Copyright
COMPOUNDS AND METHODS FOR TREATING CANCER BY INHIBITING THE UROKINASE RECEPTOR
-
Page/Page column 70; 75, (2013/03/26)
Compounds and methods for treating or preventing cancer associated with binding to the urokinase receptor are provided. Biological processes affected by the compounds include cell migration, cell growth, cell adhesion, angiogenesis, cancer cell invasion, apoptosis, tumor formation, tumor progression, metastasis, degradation of the extracellular matrix, pericellular proteolysis, activation of plasminogen, changes in the levels of an extracellular protease, and changes in the levels of a VEGF receptor.
Virtual screening targeting the urokinase receptor, biochemical and cell-based studies, synthesis, pharmacokinetic characterization, and effect on breast tumor metastasis
Wang, Fang,Li, Jing,Sinn, Anthony L.,Knabe, W. Eric,Khanna, May,Jo, Inha,Silver, Jayne M.,Oh, Kyungsoo,Li, Liwei,Sandusky, George E.,Sledge, George W.,Nakshatri, Harikrishna,Jones, David R.,Pollok, Karen E.,Meroueh, Samy O.
experimental part, p. 7193 - 7205 (2012/01/02)
Virtual screening targeting the urokinase receptor (uPAR) led to (±)-3-(benzo[d][1,3]dioxol-5-yl)-N-(benzo[d][1,3]dioxol-5-ylmethyl) -4-phenylbutan-1-amine 1 (IPR-1) and N-(3,5-dimethylphenyl)-1-(4- isopropylphenyl)-5-(piperidin-4-yl)-1H-pyrazole-4-carbox
Asymmetric cyanation of activated olefins with ethyl cyanoformate catalyzed by a modular titanium catalyst
Wang, Jun,Li, Wei,Liu, Yanling,Chu, Yangyang,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
supporting information; experimental part, p. 1280 - 1283 (2010/06/15)
"Chemical Equation Presented" Asymmetric cyanation of a class of easily available olefins with a favorable cyanide source ethyl cyanoformate (CNCOOEt) was realized by an interesting modular catalyst. High yields and ee values were obtained for a range of substrates under solvent-free and mild reaction conditions. The products obtained could be easily transformed to the enantioenriched useful intermediates 5,6, and pharmaceutically Important γ-aminobutyric acid 7.
A versatile palladium-mediated three-component reaction for the one-pot synthesis of stereodefined 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans
Bottex,Cavicchioli,Hartmann,Monteiro,Balme
, p. 175 - 179 (2007/10/03)
A one-pot reaction between equimolecular amounts of various propargyl alcohols Michael acceptors, and unsaturated halides (or triflates) in the presence of a palladium(0) catalyst provides a simple and flexible entry into highly substituted 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans. The efficiency of this palladium-mediated three-component reaction has been shown to be strongly influenced by the nature of the catalyst system, and in this regard, a palladium(0) catalyst generated in situ by reduction of PdCl2(PPh3)2 with n-butyllithium has been found particularly effective.
Process for the synthesis of α-substituted acrylic acids and their application
-
, (2008/06/13)
Process for the synthesis of a-substituted acrylic acids and their application. Process for the synthesis of a-substituted acrylic acids of general formula (I) and their application to the synthesis of N- (mercaptoacyl) aminoacid derivatives of formula (II). STR1
