Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives

• Published in: Natural product research Vol. 25; no. 3; pp. 203 - 221
• Main Authors: Zou, Hong-Bin, Zhang, Liang, Yang, Lei-Xiang, Yang, Liu-Qing, Zhao, Yu, Yu, Yong-Ping, Stöckigt, Joachim
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis Group 01.02.2011
• Subjects: alcohols; anticarcinogenic activity; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; aromatic compounds; Cell Line, Tumor; Cell Survival - drug effects; chemical reactions; cinnamic alcohol derivatives; cytotoxicity; Drug Screening Assays, Antitumor - methods; HeLa Cells; HL-60 Cells; human cell lines; Humans; inhibitory concentration 50; neoplasms; Propanols - chemistry; Propanols - pharmacology; Structure-Activity Relationship; structure-activity relationships
• ISSN: 1478-6427; 1478-6419; 1478-6427
• DOI: 10.1080/14786410902830175

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 IC₅₀ values of 0.4 and 0.5 µM, respectively. The structure–activity relationships of the derivatives are discussed.