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

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 deriva-tives(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-pro liferative 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.

Keywords

Caffeic acid / Sulphonamide / Lipophilicity / Anti-oxidant / Cytotoxicity

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