Semisynthesis of triptolide analogues: effect of B-ring substituents on cytotoxic activities

Bioorg Med Chem Lett. 2014 Dec 15;24(24):5671-5674. doi: 10.1016/j.bmcl.2014.10.069.

Hongtao Xu ¹, Yi Chen ², Huanyu Tang ¹, Huijin Feng ¹, Yuanchao Li ³

Affiliations

1 Department of Medical Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China.
2 Division of Anti-tumor Pharmacology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China.
3 Department of Medical Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China. Electronic address: ycli@mail.shcnc.ac.cn.

PMID: 25467158 DOI: 10.1016/j.bmcl.2014.10.069

Abstract

A series of B-ring modified analogues of triptolide were synthesized and tested for their cytotoxicity against two human tumor cell lines (U251 and PC-3). From the current investigation, the structure-cytotoxic activity relationships of these analogues suggested that the introduction of hydroxyl, epoxide, halogen or olefinic groups on C5 and/or C6 could still retain the cytotoxicity, albeit a little less potency, and the C7,C8-β-epoxide group of triptolide was essential to its potent cytotoxic activity.

Keywords

Cytotoxic; Diterpenoid; Structure–cytotoxic activity relationships; Synthesis; Triptolide.

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