18944-77-9Relevant articles and documents
Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie
, (2022/01/13)
This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.
Site-Selective C(sp3)–H Functionalization of Fluorinated Alkanes Driven by Polar Effects Using a Tungstate Photocatalyst
Fukuyama, Takahide,Nishikawa, Tomohiro,Ryu, Ilhyong
supporting information, p. 1424 - 1428 (2019/09/12)
The TBADT-catalyzed C(sp3)–H functionalization of perfluorophenyl- and perfluoroalkyl-substituted alkanes was studied to determine how the fluorous substituents affect site-selectivity. Alkylation of alkyl-substituted perfluorobenzene avoids α-C–H bonds, unlike their alkylbenzene counterparts, allowing site-selective functionalization of C–H bonds remote to the aromatic ring. Alkylation of alkanes having a perfluoroalkyl group also avoided α-C–H bonds. Radical polar effects in the SH2 transition states could explain this avoidance of α-C–H functionalization.
The potential role of the 5,6-dihydropyridin-2(1: H)-one unit of piperlongumine on the anticancer activity
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Yue,Mu, Wen-Wen,Yang, Jie
, p. 42128 - 42136 (2020/12/09)
Piperlongumine (PL), a potent anticancer agent from the plant long pepper (Piper longum), contains the 5,6-dihydropyridin-2(1H)-one heterocyclic scaffold and cinnamoyl unit. In this paper, we synthesized a series of PL analogs and evaluated their cytotoxicity against cancer cells for the sake of exploring which pharmacophore plays a more potent role in enhancing the anticancer activities of PL. These results illustrated that the position effect, not the electronic effect, of substituents plays a certain role in the cytotoxicity of PL and its analogs. More important, the 5,6-dihydropyridin-2(1H)-one unit, a potent pharmacophore in enhancing the antiproliferative activities of PL, could react with cysteamine and lead to ROS generation, and then bring about the occurrence of ROS-induced downstream events, followed by cell cycle arrest and apoptosis. This work suggests that introducing a lactam unit containing Michael acceptors may be a potent strategy to enhancing the anticancer activity of drugs. This journal is
