1297474-24-8Relevant academic research and scientific papers
Optimization of TRPV6 calcium channel inhibitors using a 3D ligand-based virtual screening method
Simonin, Céline,Awale, Mahendra,Brand, Michael,Van Deursen, Ruud,Schwartz, Julian,Fine, Michael,Kovacs, Gergely,H?fliger, Pascal,Gyimesi, Gergely,Sithampari, Abilashan,Charles, Roch-Philippe,Hediger, Matthias A.,Reymond, Jean-Louis
, p. 14748 - 14752 (2015)
Herein, we report the discovery of the first potent and selective inhibitor of TRPV6, a calcium channel overexpressed in breast and prostate cancer, and its use to test the effect of blocking TRPV6-mediated Ca2+-influx on cell growth. The inhib
Desymmetrizing Isomerization of Alkene via Thiazolinyl Iminoquinoline Cobalt Catalysis
Liu, Wenbo,Zheng, Yushan,Mao, Yihui,Chen, Jieping,Ren, Xiang,Cheng, Zhaoyang,Lu, Zhan
supporting information, p. 1158 - 1163 (2022/02/14)
We report a cobalt-catalyzed desymmetrizing isomerization of exo-cyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were desi
The Silicon-Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes
Zhou, Hui,Bae, Han Yong,Leutzsch, Markus,Kennemur, Jennifer L.,Bécart, Diane,List, Benjamin
supporting information, p. 13695 - 13700 (2020/08/24)
The use of chiral enol silanes in fundamental transformations such as Mukaiyama aldol, Michael, and Mannich reactions as well as Saegusa-Ito dehydrogenations has enabled the chemical synthesis of enantiopure natural products and valuable pharmaceuticals. However, accessing these intermediates in high enantiopurity has generally required the use of either stoichiometric chiral precursors or stoichiometric chiral reagents. We now describe a catalytic approach in which strongly acidic and confined imidodiphosphorimidates (IDPi) catalyze highly enantioselective interconversions of ketones and enol silanes. These "silicon-hydrogen exchange reactions"enable access to enantiopure enol silanes via tautomerizing σ-bond metatheses, either in a deprotosilylative desymmetrization of ketones with allyl silanes as the silicon source or in a protodesilylative kinetic resolution of racemic enol silanes with a carboxylic acid as the silyl acceptor.
Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
supporting information, p. 17023 - 17026,4 (2012/12/12)
Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.
Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
supporting information, p. 17023 - 17026 (2013/01/15)
Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.
Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors
Ekkati, Anil R.,Mandiyan, Valsan,Ravindranathan, Krishna P.,Bae, Jae H.,Schlessinger, Joseph,Jorgensen, William L.
scheme or table, p. 2228 - 2231 (2011/05/05)
Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC50 of 6 μM for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties.
