碘催化α-亚甲基酮的羰基化反应一锅法合成1,2-二芳基二酮和抗病毒喹喔啉类化合物

I-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot.

作者信息

Kong Lingkai, Meng Jieru, Tian Wenyue, Liu Jiazheng, Hu Xueping, Jiang Zhi-Hong, Zhang Wei, Li Yanzhong, Bai Li-Ping

机构信息

State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Guangdong-Hong Kong-Macao Joint Laboratory of Respiratory Infectious Disease, Macau University of Science and Technology, Taipa 999078, Macau, People's Republic of China.

School of Chemistry and Chemical Engineering, Linyi University, Linyi, Shandong 276000, People's Republic of China.

出版信息

ACS Omega. 2021 Dec 21;7(1):1380-1394. doi: 10.1021/acsomega.1c06017. eCollection 2022 Jan 11.

An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I. In the same oxidation system, a novel one-pot procedure was established for the construction of antiviral and anticancer quinoxalines. The reactions proceeded well with a wide variety of substrates and good functional group tolerance, affording desired compounds in moderate to excellent yields. Quinoxalines 4ca and 4ad inhibited viral entry of SARS-CoV-2 spike pseudoviruses into HEK-293T-ACE2 host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC values of 19.70 and 21.28 μM, respectively. In addition, cytotoxic evaluation revealed that 4aa, 4ba, 4ia, and 4ab suppressed four cancer cells with IC values ranging from 6.25 to 28.55 μM.