Synthesis and structure-activity relationship studies of cytotoxic cinnamic alcohol derivatives.
Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC(50) values of 0.4 and 0.5 µM, respectively. The structure-activity relationships of the derivatives are discussed.
Zou
Hong-Bin
HB
Institute of Materia Medica, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
Zhang
Liang
L
Yang
Lei-Xiang
LX
Yang
Liu-Qing
LQ
Zhao
Yu
Y
Yu
Yong-Ping
YP
Stöckigt
Joachim
J
D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor / Q000379:methods*; D018922:HL-60 Cells; D006367:HeLa Cells; D006801:Humans; D020005:Propanols / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D020005:Propanols; C020722:cinnamyl alcohol