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

[Image: see text] 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...

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Autores principales: Kong, Lingkai, Meng, Jieru, Tian, Wenyue, Liu, Jiazheng, Hu, Xueping, Jiang, Zhi-Hong, Zhang, Wei, Li, Yanzhong, Bai, Li-Ping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8757360/
https://www.ncbi.nlm.nih.gov/pubmed/35036799
http://dx.doi.org/10.1021/acsomega.1c06017
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author Kong, Lingkai
Meng, Jieru
Tian, Wenyue
Liu, Jiazheng
Hu, Xueping
Jiang, Zhi-Hong
Zhang, Wei
Li, Yanzhong
Bai, Li-Ping
author_facet Kong, Lingkai
Meng, Jieru
Tian, Wenyue
Liu, Jiazheng
Hu, Xueping
Jiang, Zhi-Hong
Zhang, Wei
Li, Yanzhong
Bai, Li-Ping
author_sort Kong, Lingkai
collection PubMed
description [Image: see text] 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.
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spelling pubmed-87573602022-01-13 I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot Kong, Lingkai Meng, Jieru Tian, Wenyue Liu, Jiazheng Hu, Xueping Jiang, Zhi-Hong Zhang, Wei Li, Yanzhong Bai, Li-Ping ACS Omega [Image: see text] 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. American Chemical Society 2021-12-21 /pmc/articles/PMC8757360/ /pubmed/35036799 http://dx.doi.org/10.1021/acsomega.1c06017 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kong, Lingkai
Meng, Jieru
Tian, Wenyue
Liu, Jiazheng
Hu, Xueping
Jiang, Zhi-Hong
Zhang, Wei
Li, Yanzhong
Bai, Li-Ping
I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot
title I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot
title_full I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot
title_fullStr I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot
title_full_unstemmed I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot
title_short I(2)-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot
title_sort i(2)-catalyzed carbonylation of α-methylene ketones to synthesize 1,2-diaryl diketones and antiviral quinoxalines in one pot
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8757360/
https://www.ncbi.nlm.nih.gov/pubmed/35036799
http://dx.doi.org/10.1021/acsomega.1c06017
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