192711-11-8Relevant articles and documents
DMAP Mediated Efficient Construction of Functionalized Chromenes through One-Pot Reaction of para-Quinone Methides with Allenoates
Song, Zefeng,Jia, Yuping,Zhang, Daizhou,Wang, De
supporting information, p. 1942 - 1948 (2021/04/05)
A novel DMAP-mediated Rauhut-Currier/oxa-Michael addition cascade reaction of hydroxylphenyl-substituted para-quinone methide with allenoate was reported for the first time. A series of functionalized chromenes were successfully obtained with moderate to
Cyclization Reaction-Based Turn-on Probe for Covalent Labeling of Target Proteins
Fujita, Yuki,Ikebe, Yuka,Itoh, Toshimasa,Kojima, Hiroyuki,Ohashi, Nami,Takeuchi, Ryosuke,Yamamoto, Keiko
, p. 334 - 349 (2020/03/17)
Fluorescent molecules have contributed to basic biological research but there are currently only a limited number of probes available for the detection of non-enzymatic proteins. Here, we report turn-on fluorescent probes mediated by conjugate addition and cyclization (TCC probes). These probes react with multiple amino acids and exhibit a 36-fold greater emission intensity after reaction. We analyzed the reactions between TCC probes and nuclear receptors by electrospray ionization mass spectrometry, X-ray crystallography, spectrofluorometry, and fluorescence microscopy. In vitro analysis showed that probes consisting of a protein ligand and TCC could label vitamin D receptor and peroxisome proliferator-activated receptor γ. Moreover, we demonstrated that not only a ligand unit but also a peptide unit can label the target protein in a complex mixture. Non-enzymatic proteins are challenging targets for turn-on probes. Here, Kojima et al. report turn-on fluorescent probes mediated by conjugate addition and cyclization (TCC probes). These probes react with nuclear receptors and emit bright fluorescence after the reaction. TCC probes are potent tools for molecular imaging and chemical proteomics.
Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans
Chen, Ke,Liu, Shuai,Wang, Dan,Hao, Wen-Juan,Zhou, Peng,Tu, Shu-Jiang,Jiang, Bo
supporting information, p. 11524 - 11530 (2017/11/10)
The combination of AgTFA and Sc(OTf)3 enables the bimetallic synergistic catalysis of β-alkynyl ketones and para-quinone methides (p-QMs), allowing direct synthesis of 17 examples of benzo[c]xanthenes with generally good yields through a benzannulation/1,6-addition/cyclization sequence. Exchanging p-QMs for quinone imine ketal resulted in 10 examples of tetracyclic naphtho[1,2-b]benzofurans via a similar benzannulation/1,4-addition/cyclization cascade. During these reaction processes, AgTFA and Sc(OTf)3 could be perfectly compatible, together with the realization of C(sp3)-H functionalization adjacent to carbonyl group on the β-alkynyl ketone unit.