One-pot synthesis of 1,4-dihydroxy-2-((E)-1-hydroxy-4-phenylbut-3-enyl)anthracene-9,10-diones as novel shikonin analogs and evaluation of their antiproliferative activities.
One-pot synthesis of 1,4-dihydroxy-2-((E)-1-hydroxy-4-phenylbut-3-enyl)anthracene-9,10-diones as novel shikonin analogs and evaluation of their antiproliferative activities.
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新型紫草素类似物1,4-二羟基-2-((E)-1-羟基-4-苯基丁-3-烯基)蒽-9,10-二酮的一锅合成及其抗增殖活性评价。
DOI：
10.1016/j.bmcl.2016.04.006
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发表时间：
2016
影响因子：
2.7
通讯作者：
Wang,Guangdi
中科院分区：
文献类型：
--
作者：
Zhao,Li-Ming;Cao,Feng-Xia;Jin,Hai-Shan;Zhang,Jie-Huan;Szwaya,Jeffrey;Wang,Guangdi
在温和的条件下，以奎宁苷和β，γ-不饱和醛为原料，在甲醇中一锅法合成了一系列紫草素类似物，并研究了它们对4种癌细胞株和1种正常细胞株的细胞毒活性。合成的化合物对HeLa细胞具有细胞毒性，对正常细胞系无明显毒性。进一步的修饰导致发现了一种新的四环蒽醌（4 b/4 b ′），其对宫颈癌、乳腺癌和胰腺癌细胞系具有强效细胞毒活性，对对照乳腺上皮细胞系MCF-10的生长无显著影响。化合物4 b/4 b ′具有良好的细胞毒性和选择性，有望成为进一步优化的先导化合物。
A series of shikonin analogs have been synthesized in a one-pot reaction of quinizarin with β,γ-unsaturated aldehydes in MeOH under mild conditions and investigated for their cytotoxicity against four cancer cell lines and one normal cell line. The synthesized compounds were found to be cytotoxic against HeLa cells with no apparent toxicity against normal cell line. Further modification led to the discovery of a novel tetracyclic anthraquinone (4b/4b′) with potent cytotoxic activities against cervical, breast and pancreatic cancer cell lines with no significant effect on the growth of the control mammary epithelial cell line MCF-10. The good cytotoxicity and selectivity of compound4b/4b′ suggest that it could be a promising lead for further optimization.