Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

Total synthesis of novel D-ring-modified triptolide analogues: structure–cytotoxic activity relationship studies on the D-ring of triptolide†

Bing Zhou,a   Xiaomei Li,a   Huanyu Tang,a   Zehong Miao,a   Huijin Fenga  and  Yuanchao Li*a  

* Corresponding authors

a Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Road Zu Chong Zhi, Zhangjiang Hi-Tech Park, Shanghai, PR China
E-mail: ycli@mail.shcnc.ac.cn
Fax: + 86-21-50807288
Tel: + 86-21-50806600 ext 3502

Abstract

The total synthesis of a trans-position butenolide analogue of triptolide 3 and the semi-synthesis of analogue 4, with a furan ring, and compound 5, without a planar D-ring, are described. Studies into the antitumor activity of these compounds suggest that the five-membered unsaturated lactone ring (D-ring) of triptolide is essential to its potent anticancer activity and the C18 carbonyl group may exert an important influence on the interaction between triptolide and the target molecule(s) responsible for initiating their cytotoxic effects.

Graphical abstract: Total synthesis of novel D-ring-modified triptolide analogues: structure–cytotoxic activity relationship studies on the D-ring of triptolide

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Article information

DOI
https://doi.org/10.1039/C0OB01239D
Article type
Paper
Submitted
23 Dec 2010
Accepted
14 Feb 2011
First published
15 Feb 2011

Org. Biomol. Chem., 2011,9, 3176-3179

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Total synthesis of novel D-ring-modified triptolide analogues: structure–cytotoxic activity relationship studies on the D-ring of triptolide

B. Zhou, X. Li, H. Tang, Z. Miao, H. Feng and Y. Li, Org. Biomol. Chem., 2011, 9, 3176 DOI: 10.1039/C0OB01239D

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