I 2 -Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot.
Lingkai KongJieru MengWenyue TianJiazheng LiuXueping HuZhi-Hong JiangWei ZhangYanzhong LiLi-Ping BaiPublished in: ACS omega (2021)
An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I 2 . 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 h host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC 50 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 50 values ranging from 6.25 to 28.55 μM.
Keyphrases
- sars cov
- angiotensin converting enzyme
- angiotensin ii
- induced apoptosis
- endothelial cells
- respiratory syndrome coronavirus
- cell cycle arrest
- induced pluripotent stem cells
- high intensity
- minimally invasive
- hydrogen peroxide
- endoplasmic reticulum stress
- oxidative stress
- signaling pathway
- pluripotent stem cells
- binding protein
- cell proliferation
- protein kinase