Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents.
A series of new bromophenols and chlorophenols were prepared by a practical route. The in vitro antioxidative activity of the halophenols was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, and their cytoprotective activity was also tested on hydrogen peroxide (H(2)O(2))-induced injury in human umbilical vein endothelial cells (HUVEC). All halophenols tested displayed moderate to good DPPH radical-scavenging activity, and two bromophenols, 2,3'-dibromo-4,5,6'-trihydroxydiphenylmethanone (16c) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone (17c) exhibited high protective activity against H(2)O(2)-induced injury in HUVEC with EC(50) values of 0.4 and 0.8 microM, respectively. The preliminary structure-activity relationships of these compounds were also investigated in order to determine the essential structures required for their bioactivities.
Zhao
Wanyi
W
School of Pharmaceutical Science, Shanxi Medical University, Taiyuan 030001, China.
Feng
Xiue
X
Ban
Shurong
S
Lin
Wenhan
W
Li
Qingshan
Q
D000975:Antioxidants / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects*; D002478:Cells, Cultured; D004730:Endothelium, Vascular / Q000166:cytology / Q000187:drug effects; D006219:Halogens / Q000737:chemistry*; D006801:Humans; D010636:Phenols / Q000737:chemistry / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
D000975:Antioxidants; D006219:Halogens; D010636:Phenols