154258-38-5Relevant articles and documents
Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks
Thomas, Joice,Goyvaerts, Vince,Liekens, Sandra,Dehaen, Wim
supporting information, p. 9966 - 9970 (2016/07/19)
Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.
Highly fluorinated (σ-Aryl)-chelating titanium(IV) post-metallocene: Characterization and scalar [C-H???F-C] coupling
Liu, Cham-Chuen,So, Loi-Chi,Lo, Jerry C. Y.,Chan, Michael C. W.,Kaneyoshi, Hiromu,Makio, Haruyuki
, p. 5274 - 5281 (2012/11/07)
The observation of weak intramolecular C-H???F-C interactions in group 4 (σ-aryl)-chelating complexes using NMR spectroscopic and neutron diffraction studies was recently reported. In this work, a new titanium(IV) catalyst precursor supported by a tridentate pyridine-2-phenolate-6-(σ-aryl) ligand, featuring a metal center surrounded by multiple CF3 substituents, has been synthesized. The nature of intramolecular interactions in the bis(benzyl) complex in solution was probed using multinuclear NMR spectroscopic experiments (including [ 1H,19F]-HMQC and -HMBC), which reveal scalar coupling across C-H???F-C interactions between methylene hydrogens and the proximal CF3 group on the σ-aryl (but not the phenolate) moiety. High activities are observed for ethylene polymerization at different temperatures, which exceed those for the tBu-phenolate congener.
Novel thienopyridine derivatives as specific anti-hepatocellular carcinoma (HCC) agents: Synthesis, preliminary structure-activity relationships, and in vitro biological evaluation
Zeng, Xiu-Xiu,Zheng, Ren-Lin,Zhou, Tian,He, Hai-Yun,Liu, Ji-Yan,Zheng, Yu,Tong, Ai-Ping,Xiang, Ming-Li,Song, Xiang-Rong,Yang, Sheng-Yong,Yu, Luo-Ting,Wei, Yu-Quan,Zhao, Ying-Lan,Yang, Li
supporting information; experimental part, p. 6282 - 6285 (2010/12/18)
Novel thienopyridine derivatives 1b-1r were synthesized, based on a hit compound 1a that was found in a previous cell-based screening of anticancer drugs. Compounds 1a-1r have the following features: (1) their anticancer activity in vitro was first reported by our group. (2) The most potent analog 1g possesses hepatocellular carcinoma (HCC)-specific anticancer activity. It can specifically inhibit the proliferation of the human hepatoma HepG2 cells with an IC50 value of 0.016 μM (compared with doxorubicin as a positive control, whose IC50 was 0.37 μM). It is inactive toward a panel of five different types of human cancer cell lines. (3) Compound 1g remarkably induces G0/G1 arrest and apoptosis in HepG2 cells in vitro at low micromolar concentrations. These results, especially the HCC-specific anticancer activity of 1g, suggest their potential in targeted chemotherapy for HCC.
