364-57-8Relevant academic research and scientific papers
Flavonol dyes with different substituents in photopolymerization
You, Jian,Fu, Hongyuan,Zhao, Di,Hu, Tianyu,Nie, Jun,Wang, Tao
, (2020)
To further expand the applications of flavonol dyes (3HFs) in photopolymerization, six flavonol dyes with different substituents were prepared by using the Algar–Flynn–Oyamada method. The steady-state photolysis and fluorescence quenching of 3HFs under the 385 nm LED light source showed that the proton transfer reaction preceded the charge transfer reaction between 3HFs and triethanolamine (TEOA) or iodonium salts (ONI), and groups with different electron properties could affect the photochemistry of 3HFs. The influence of substituents on the free radical polymerization efficiencies of 3HFs/TEOA and 3HFs/ONI was evaluated. Results showed that charge transfer occurred in the oxidation or reduction processes between 3HFs and TEOA or ONI. The possible mechanism was speculated, and the thermal feasibility of charge transfer between 3HFs and TEOA or ONI was calculated on the basis of the free energy changes of photoinduced electron transfer.
Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone
Xiong, Wei,Wang, Xiaohong,Shen, Xianyan,Hu, Cuifang,Wang, Xin,Wang, Fei,Zhang, Guolin,Wang, Chun
supporting information, p. 13160 - 13176 (2020/11/23)
A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.
Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
Zheng, Yuanyuan,Pu, Wenchen,Li, Jiao,Shen, Xianyan,Zhou, Qiang,Fan, Xin,Yang, Sheng-Yong,Yu, Yamei,Chen, Qiang,Wang, Chun,Wu, Xin,Peng, Yong
, p. 130 - 134 (2018/11/30)
Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.
Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction
Kaishap, Partha P.,Duarah, Gauri,Sarma, Bipul,Chetia, Dipak,Gogoi, Sanjib
, p. 456 - 460 (2018/02/21)
The first decarbonylative insertion of an alkyne through C?H/C?C activation of six-membered compounds is reported. The Ru-catalyzed reaction of 3-hydroxy-2-phenyl-chromones with alkynes works most efficiently in the presence of the ligand PPh3 to provide spiro-indenebenzofuranones. Unlike previously reported metal-catalyzed decarbonylative annulation reactions, in the present decarbonylative annulation reaction, the annulation occurs before extrusion of carbon monoxide.
