Asymmetric synthesis of chiral (thio)chromanes and exploration on their structure-activity relationship in macrophages

Zhang, Xiao1,2; Zhou, Qian3; Zhou, Yue3; Wang, Zihao5,6; Wang, Jun2,4; Wang, Mingfu1,3

2023-10-11

10.1039/d3ra06428j

RSC ADVANCES   影响因子和分区

2046-2069

["A CuCl/(R,R)-Ph-BPE-catalyzed enantioselective hydroallylation of 2H-chromenes and 2H-thiochromenes with allylic phosphate electrophiles is developed, which enables highly efficient and atom-economical asymmetric access to a series of 4-allyl chromanes and thiochromanes in high yields (up to 91%) with excellent enantioselectivities (up to 99% ee). These valuable chiral chromane and thiochromane products can serve as crucial intermediates for accessing bioactive compounds containing oxygen and sulfur atoms. In addition, the antioxidant and anti-inflammatory effects of various chromanes and thiochromanes were investigated in RAW 264.7 macrophages. The chromanes and thiochromanes exhibited significant inhibitory effects on the production of reactive oxygen species (ROS) and the secretion of pro-inflammatory cytokines, including interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-alpha). These findings indicate that the newly synthesized chromanes and thiochromanes hold promise as potential lead compounds for the development of antioxidant and anti-inflammatory drugs.","A CuCl/(R,R)-Ph-BPE-catalyzed enantioselective hydroallylation of 2H-(thio)chromenes is developed, which enables access to a series of 4-allyl (thio)chromanes in high yields (up to 91%) with excellent enantioselectivities (up to 99% ee)."]

SCI ; EI

英语

其他

This work was supported by Shenzhen Science and Technology Program (ZDSYS20220117155800001), Health@InnoHK Initiative Fund of the Hong Kong Special Administrative Region Government (ITC RC/IHK/4/7), and Shenzhen Basic Research Program for Shenzhen Virtual[ZDSYS20220117155800001] ; Shenzhen Science and Technology Program[ITC RC/IHK/4/7] ; Health@InnoHK Initiative Fund of the Hong Kong Special Administrative Region Government[2021Szvup132]

Chemistry

Chemistry, Multidisciplinary

WOS:001083235000001

ROYAL SOC CHEMISTRY

20234415003798

Antioxidants ; Cell death ; Copper compounds ; Enantioselectivity ; Lead compounds ; Oxygen

Biology:461.9 ; Immunology:461.9.1 ; Physical Chemistry:801.4 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804 ; Organic Compounds:804.1 ; Inorganic Compounds:804.2

Web of Science

1.Univ Hong Kong, Sch Biol Sci, Hong Kong 999077, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
3.Shenzhen Univ, Inst Adv Study, Shenzhen Key Lab Food Nutr & Hlth, Shenzhen 518060, Peoples R China
4.Hong Kong Baptist Univ, Dept Chem, Hong Kong 999077, Peoples R China
5.Hong Kong Baptist Univ, Sch Chinese Med, Hong Kong 999077, Peoples R China
6.Hong Kong Baptist Univ, Ctr Chinese Herbal Med Drug Dev, Hong Kong 999077, Peoples R China

Zhang, Xiao,Zhou, Qian,Zhou, Yue,et al. Asymmetric synthesis of chiral (thio)chromanes and exploration on their structure-activity relationship in macrophages[J]. RSC ADVANCES,2023,13(43):30391-30400.

Zhang, Xiao,Zhou, Qian,Zhou, Yue,Wang, Zihao,Wang, Jun,&Wang, Mingfu.(2023).Asymmetric synthesis of chiral (thio)chromanes and exploration on their structure-activity relationship in macrophages.RSC ADVANCES,13(43),30391-30400.

Zhang, Xiao,et al."Asymmetric synthesis of chiral (thio)chromanes and exploration on their structure-activity relationship in macrophages".RSC ADVANCES 13.43(2023):30391-30400.