I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot

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

doi:10.1021/acsomega.1c06017

I₂-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot

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

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I2. 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-ACE2h host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC50 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 IC50 values ranging from 6.25 to 28.55 μM.

Original language	English
Pages (from-to)	1380-1394
Number of pages	15
Journal	ACS Omega
Volume	7
Issue number	1
DOIs	https://doi.org/10.1021/acsomega.1c06017
State	Published - 11 Jan 2022

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acsomega.1c06017

Cite this

@article{6f5556e35a74401c9474b34b96f85722,

title = "I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot",

abstract = "An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I2. 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-ACE2h host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC50 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 IC50 values ranging from 6.25 to 28.55 μM.",

author = "Lingkai Kong and Jieru Meng and Wenyue Tian and Jiazheng Liu and Xueping Hu and Jiang, \{Zhi Hong\} and Wei Zhang and Yanzhong Li and Bai, \{Li Ping\}",

year = "2022",

month = jan,

day = "11",

doi = "10.1021/acsomega.1c06017",

language = "英语",

volume = "7",

pages = "1380--1394",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot

AU - Kong, Lingkai

AU - Meng, Jieru

AU - Tian, Wenyue

AU - Liu, Jiazheng

AU - Hu, Xueping

AU - Jiang, Zhi Hong

AU - Zhang, Wei

AU - Li, Yanzhong

AU - Bai, Li Ping

PY - 2022/1/11

Y1 - 2022/1/11

N2 - An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I2. 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-ACE2h host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC50 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 IC50 values ranging from 6.25 to 28.55 μM.

AB - An efficient approach for the synthesis of 1,2-diaryl diketones was developed from readily available α-methylene ketones by catalysis of I2. 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-ACE2h host cells as dual blockers of both human ACE2 receptor and viral spike RBD with IC50 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 IC50 values ranging from 6.25 to 28.55 μM.

UR - https://www.scopus.com/pages/publications/85121999949

U2 - 10.1021/acsomega.1c06017

DO - 10.1021/acsomega.1c06017

M3 - 文章

AN - SCOPUS:85121999949

SN - 2470-1343

VL - 7

SP - 1380

EP - 1394

JO - ACS Omega

JF - ACS Omega

IS - 1

ER -

I₂-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot

Abstract

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this