Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues.

A series of novel β-hydroxyisovalerylshikonin analogues bearing oxygen-containing substituents at the side-chain hydroxyl of shikonin were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against multi-drug resistant (MDR) cell lines DU-145 and HeLa. Most compounds exhibited significant inhibitory activity on both cell lines. The structure-activity relationship showed the analogues with ether substituents displayed the most potent antitumour activity and selective cytotoxicity towards DU-145. Among the compounds with ether substituents, increasing the steric hindrance in the carbon bearing β-hydroxyl or replace the β-hydroxyl with acetoxy or methoxy would lead to the decline of cytotoxicity. Copyright © 2011 Elsevier Masson SAS. All rights reserved.

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Zhen Rao, Xin Liu, Wen Zhou, Jing Yi, Shao-Shun Li. Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues. European journal of medicinal chemistry. 2011 Sep;46(9):3934-41

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PMID: 21689869

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