1. One-pot construction of functionalized aziridines and maleimides via a novel pseudo-Knoevenagel cascade reaction
- Author
-
Jie Lei, Gui-Ting Song, Liu-Jun He, Ya-Fei Luo, Dian-Yong Tang, Hui-Kuan Lin, Brendan Frett, Hong-yu Li, Zhong-Zhu Chen, and Zhi-Gang Xu
- Subjects
Molecular Structure ,Cell Survival ,010405 organic chemistry ,Aziridines ,Metals and Alloys ,Antineoplastic Agents ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Catalysis ,0104 chemical sciences ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,Maleimides ,Cell Line, Tumor ,Materials Chemistry ,Ceramics and Composites ,Humans ,Drug Screening Assays, Antitumor ,Cell Proliferation - Abstract
An Ugi, novel pseudo-Knoevenagel, ring expansion cascade reaction was discovered and utilized for the synthesis of aziridinyl succinimides in one-pot. Subsequently, densely functionalized aziridines and maleimides have been designed and synthesized through similar cascade reactions. The target compounds were prepared by means of a mild reaction and a simple operation procedure, which could be applicable to a broad scope of starting materials. This series of novel cascade reactions generates opportunities for the tailored synthesis of a wide range of biologically active scaffolds through tuneable Ugi inputs. Discovery of compound 8i with comparable potency to sorafenib in liver cancer cell lines could provide a new avenue for liver cancer drug discovery.
- Published
- 2020