Issue 9, 2011

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2010
Accepted
14 Feb 2011
First published
15 Feb 2011

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

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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