N-Arylation of Amino Acid Esters via an I₂-Mediated Metal-Free Multicomponent Benzannulation Strategy

Huang, Wenbo2; Rao, Xiaofeng3,4; Shi, Liqiao1; Yang, Bing2; Kuang, Buxiao2; Wu, Hongqu1; Ke, Shaoyong1; Liu, Changhui5

2023-11-15

10.1021/acs.joc.3c01907

JOURNAL OF ORGANIC CHEMISTRY   影响因子和分区

0022-3263

1520-6904

Herein, we present a novel method for the N-arylation of amino acid esters using alpha-bromoacetaldehyde acetal and acetoacetate via an I2-mediated metal-free benzannulation strategy, which disclosed the first synthetic application of N-arylation of amino acids using nonaromatic building blocks. The synthesized N-arylated amino acid derivatives were found to possess promising selective inhibition against human hepatocellular liver carcinoma cells, human melanoma cells, and human normal liver cells, with an IC50 value as low as 16.79 mu g center dot( -1).

SCI ; EI

英语

通讯

Innovation and Application of Key Technologies of Quality-improving and Efficiency-increasing of Fengtou Ginger Industry[2021A1515012341] ; Natural Science Foundation of Guangdong Province[51906252] ; National Natural Science Foundation of China[BK20190632] ; Natural Science Foundation of Jiangsu Province[2019M661980] ; China Postdoctoral Science Foundation["L2018031","2020-620-002-06"] ; Hubei Academy of Agricultural Sciences[2021-620-000-001-027]

Chemistry

Chemistry, Organic

WOS:001113306000001

AMER CHEMICAL SOC

20234915173636

Aromatic compounds ; Chemical reactions ; Esters

Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

2-s2.0-85178554605

Web of Science

1.Hubei Acad Agr Sci, Minist Agr & Rural Affairs, Hubei Biopesticide Engn Res Ctr, Key Lab Microbial Pesticides, Wuhan 430064, Peoples R China
2.Hubei Three Gorges Lab, Yichang 443007, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
4.Shenzhen Bay Lab, Shenzhen 518055, Peoples R China
5.China Univ Min & Technol, Sch Low Carbon Energy & Power Engn, Xuzhou 221116, Peoples R China

Huang, Wenbo,Rao, Xiaofeng,Shi, Liqiao,et al. N-Arylation of Amino Acid Esters via an I₂-Mediated Metal-Free Multicomponent Benzannulation Strategy[J]. JOURNAL OF ORGANIC CHEMISTRY,2023,88(23):16649-16654.

Huang, Wenbo.,Rao, Xiaofeng.,Shi, Liqiao.,Yang, Bing.,Kuang, Buxiao.,...&Liu, Changhui.(2023).N-Arylation of Amino Acid Esters via an I₂-Mediated Metal-Free Multicomponent Benzannulation Strategy.JOURNAL OF ORGANIC CHEMISTRY,88(23),16649-16654.

Huang, Wenbo,et al."N-Arylation of Amino Acid Esters via an I₂-Mediated Metal-Free Multicomponent Benzannulation Strategy".JOURNAL OF ORGANIC CHEMISTRY 88.23(2023):16649-16654.