中文版 | English
题名

Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity

作者
发表日期
2022-06-03
DOI
发表期刊
ISSN
2375-2548
EISSN
2375-2548
卷号8期号:22
摘要

Flavanols are privileged heterocyclic compounds in medicinal chemistry. It is notable to develop an efficient and straightforward protocol for accessing chiral flavanols with precise control of the stereocenters. Here, a highly efficient kinetic resolution of chromenes was reported via Cu-catalyzed asymmetric hydroboration. This previously unidentified approach features a one-step synthesis of chiral flavan-3-ols containing two vicinal stereogenic centers via a highly efficient kinetic resolution (s factor up to 1060, >99% ee for most products). In addition, the anti-inflammation effects of these diversified flavan-3-ols were studied by the in vitro experiments and RNA sequencing analysis. These flavan-3-ols showed inhibitory effects on the secretion of pro-inflammation cytokines including interleukin-1β (IL-1β), IL-6, and tumor necrosis factor-α (TNF-α), as well as inhibiting the inflammation responses through down-regulating the gene transcriptions closely related to PI3K-Akt signaling pathway and TNF signaling pathway. The results suggested that these newly synthesized flavan-3-ols have the potential to be lead compounds for anti-inflammatory drugs.

相关链接[Scopus记录]
收录类别
SCI ; EI
语种
英语
重要成果
NI论文
学校署名
其他
资助项目
Guangdong Innovative Program[2019BT02Y335]
WOS研究方向
Science & Technology - Other Topics
WOS类目
Multidisciplinary Sciences
WOS记录号
WOS:000808053900020
出版者
EI入藏号
20222512241930
EI主题词
Catalysis ; Cell Death ; Kinetics ; Lead Compounds ; Pathology ; Stereochemistry ; Transcription
EI分类号
Medicine And Pharmacology:461.6 ; Biology:461.9 ; Fluid Flow, General:631.1 ; Chemistry:801 ; Chemical Reactions:802.2 ; Organic Compounds:804.1 ; Classical Physics ; Quantum Theory ; Relativity:931
Scopus记录号
2-s2.0-85131701317
来源库
Scopus
引用统计
被引频次[WOS]:14
成果类型期刊论文
条目标识符http://sustech.caswiz.com/handle/2SGJ60CL/336244
专题理学院_化学系
作者单位
1.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
2.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
3.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
4.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
5.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
6.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
7.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
8.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
9.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
10.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
11.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
12.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
13.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
14.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
15.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
16.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
17.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
18.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
19.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
20.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
21.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
22.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
23.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
24.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
25.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
26.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
27.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
28.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
29.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
30.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
31.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
32.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
33.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
34.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
35.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
36.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
37.Department of Chemistry,Hong Kong Baptist University,Hong Kong,
38.Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China
39.School of Chinese Medicine,Hong Kong Baptist University,Hong Kong,
40.School of Pharmaceutical Sciences,Shenzhen University,Shenzhen,Health Science Center,518066,China
第一作者单位化学系
推荐引用方式
GB/T 7714
Yang,Qingjing,Wang,Zihao,Hor,Catherine Hong Huan,et al. Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity[J]. Science Advances,2022,8(22).
APA
Yang,Qingjing.,Wang,Zihao.,Hor,Catherine Hong Huan.,Xiao,Haitao.,Bian,Zhaoxiang.,...&Wang,Jun Joelle.(2022).Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity.Science Advances,8(22).
MLA
Yang,Qingjing,et al."Asymmetric synthesis of flavanols via Cu-catalyzed kinetic resolution of chromenes and their anti-inflammatory activity".Science Advances 8.22(2022).
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