Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications

doi:10.1007/s40242-020-0014-5

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (5): 795-803.doi: 10.1007/s40242-020-0014-5

Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications

PENG Xiaoyu^1,5, ZHAO Anran³, HUANG Kelin⁵, HU Tingju¹, LIU Buming⁴, HUANG Yan⁴, CHEN Hailan^1,2, CHAI Ling⁴, LIN Cuiwu¹

1. School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, P. R. China;
2. School of Animal Science and Technology, Guangxi University, Nanning 530004, P. R. China;
3. Laboratory Medicine Department, First Affiliated Hospital of Guangxi Medical University, Nanning 530021, P. R. China;
4. Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Guangxi Institute of Traditional Medical and Pharmaceutical Sciences, Nanning 530022, P. R. China;
5. China Academy of Science and Technology Development Guangxi Branch, Nanning 530022, P. R. China

收稿日期:2020-01-16 修回日期:2020-04-21 出版日期:2020-10-01 发布日期:2020-10-01
通讯作者: CHEN Hailan, CHAI Ling, LIN Cuiwu E-mail:hlchen@gxu.edu.cn;cicichai001@163.com;lincuiwu@gxu.edu.cn
基金资助:
Supported by the Guangxi Natural Science Foundation, China(No.2016GXNSFBA380053) and the Fund of the Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, China(No.Guizhongzhongkai201505).

Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications

PENG Xiaoyu^1,5, ZHAO Anran³, HUANG Kelin⁵, HU Tingju¹, LIU Buming⁴, HUANG Yan⁴, CHEN Hailan^1,2, CHAI Ling⁴, LIN Cuiwu¹

1. School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, P. R. China;
2. School of Animal Science and Technology, Guangxi University, Nanning 530004, P. R. China;
3. Laboratory Medicine Department, First Affiliated Hospital of Guangxi Medical University, Nanning 530021, P. R. China;
4. Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Guangxi Institute of Traditional Medical and Pharmaceutical Sciences, Nanning 530022, P. R. China;
5. China Academy of Science and Technology Development Guangxi Branch, Nanning 530022, P. R. China

Received:2020-01-16 Revised:2020-04-21 Online:2020-10-01 Published:2020-10-01
Contact: CHEN Hailan, CHAI Ling, LIN Cuiwu E-mail:hlchen@gxu.edu.cn;cicichai001@163.com;lincuiwu@gxu.edu.cn
Supported by:
Supported by the Guangxi Natural Science Foundation, China(No.2016GXNSFBA380053) and the Fund of the Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, China(No.Guizhongzhongkai201505).

摘要/Abstract

摘要： Structural modification of native compounds is an effective way to develop new drugs with increased pharmacological activities and improved material characteristics. In this study, caffeic acid sulphonamide derivatives(CSs) were synthesised by conjugating sulphonamides to the backbone of caffeic acid. The structures of these derivatives were elucidated by means of Fourier transform infrared spectroscopy(FTIR), ¹H NMR, ¹³C NMR, and electrospray ionization mass spectroscopy(ESI-MS). A content determination method was established by ultraviolet detection. The lipophilicity, 2,2-diphenyl-1-picrylhydrazy free radical(DPPH) scavenging capacity, anti-coagulant effects, anti-bacterial activity, cytotoxicity, in vitro anti-proliferative activity against tumour cells, and the ability of the compounds to promote the proliferation of chondrocytes were evaluated. The results indicate that CSs exhibit strong DPPH scavenging activity, high lipophilicity, good anti-coagulant activities, wide anti-bacterial activity range, low cytotoxicity, and an excellent ability to promote chondrocyte proliferation.

关键词: Caffeic acid, Sulphonamide, Lipophilicity, Anti-oxidant, Cytotoxicity

Abstract: Structural modification of native compounds is an effective way to develop new drugs with increased pharmacological activities and improved material characteristics. In this study, caffeic acid sulphonamide derivatives(CSs) were synthesised by conjugating sulphonamides to the backbone of caffeic acid. The structures of these derivatives were elucidated by means of Fourier transform infrared spectroscopy(FTIR), ¹H NMR, ¹³C NMR, and electrospray ionization mass spectroscopy(ESI-MS). A content determination method was established by ultraviolet detection. The lipophilicity, 2,2-diphenyl-1-picrylhydrazy free radical(DPPH) scavenging capacity, anti-coagulant effects, anti-bacterial activity, cytotoxicity, in vitro anti-proliferative activity against tumour cells, and the ability of the compounds to promote the proliferation of chondrocytes were evaluated. The results indicate that CSs exhibit strong DPPH scavenging activity, high lipophilicity, good anti-coagulant activities, wide anti-bacterial activity range, low cytotoxicity, and an excellent ability to promote chondrocyte proliferation.

Key words: Caffeic acid, Sulphonamide, Lipophilicity, Anti-oxidant, Cytotoxicity

PENG Xiaoyu, ZHAO Anran, HUANG Kelin, HU Tingju, LIU Buming, HUANG Yan, CHEN Hailan, CHAI Ling, LIN Cuiwu. Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications[J]. 高等学校化学研究, 2020, 36(5): 795-803.

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Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications

Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications

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