42528-36-9Relevant academic research and scientific papers
Synthesis of N-Carbonyl Acridanes as Highly Potent Inhibitors of Tubulin Polymerization via One-Pot Copper-Catalyzed Dual Arylation of Nitriles with Cyclic Diphenyl Iodoniums
Peng, Xiaopeng,Li, Ling,Ren, Yichang,Xue, Huanxin,Liu, Jin,Wen, Shijun,Chen, Jianjun
, p. 2030 - 2038 (2020)
A novel Copper-catalyzed cascade reaction between six-membered cyclic diaryliodonium salts and nitriles is reported for the facile access to a variety of N-carbonyl acridanes in good to excellent yields (up to 82%). The reaction is efficient and atom-economical with a broad substrate scope (e. g. both aryl / alkyl nitriles and substituted / unsubstituted cyclic diaryliodonium salts compatible in the system). This method is particularly useful for the synthesis of substituted N-carbonyl acridanes which are present in many pharmaceutically important compounds, but are not easy to obtain in conventional approaches. Furthermore, one of the newly synthesized acridanes displayed high antiproliferative activity against MB-468 cancer cells (IC50=26 nM, comparable to paclitaxel and colchicine) by inhibiting tubulin polymerization. Together, these findings might grant a rapid access to a novel molecular scaffold with potential anticancer utilities. (Figure presented.).
Copper-Catalyzed N,N-Diarylation of Amides for the Construction of 9,10-Dihydroacridine Structure and Applications in the Synthesis of Diverse Nitrogen-Embedded Polyacenes
Tan, Mei-Ling,Tong, Shuo,Hou, Sheng-Kai,You, Jingsong,Wang, Mei-Xiang
, p. 5417 - 5422 (2020/07/08)
We reported herein CuI/DMEDA catalyzed N,N-diarylation reaction of amides with various di(o-bromoaryl)methanes to produce diverse 9,10-dihydroacridine derivatives. The resulting 9,10-dihydroacridine derivatives were oxidized selectively under mild conditions to afford acridine, acridinone, and acridinium derivatives. The copper-catalyzed N,N-diarylation reaction coupled with oxidative aromatization reaction enabled the facile construction of nitrogen atom-embedded tetracenes and pentacenes of different ortho-fused patterns. The luminescence properties, especially the effect of fusion pattern on fluorescence emission of acquired N-polycenes, were also demonstrated.
