Systemic study on the biogenic pathways of yezo’otogirins: total synthesis and antitumor activities of (±)-yezo’otogirin C and its structural analogues.
Systemic study on the biogenic pathways of yezo’otogirins: total synthesis and antitumor activities of (±)-yezo’otogirin C and its structural analogues.
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DOI：
10.1021/jo502267g
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发表时间：
2015-01
期刊：
影响因子：
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通讯作者：
Wei Yang;Jingming Cao;Mengxun Zhang;Rongfeng Lan;Lizhi Zhu;Guangyan Du;Shuzhong He;Chi-Sing Lee
中科院分区：
文献类型：
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作者：
Wei Yang;Jingming Cao;Mengxun Zhang;Rongfeng Lan;Lizhi Zhu;Guangyan Du;Shuzhong He;Chi-Sing Lee
本文系统地研究了在好氧和厌氧条件下生成yezo 'otogirin C的仿生途径，发现根据生理条件，这两种途径都是天然产物的可行途径。由于活化能较低，当体内氧水平较高时，好氧过程更有利。在本研究过程中，从一种现成的化合物出发，在不使用任何保护基团的情况下，通过四步（31%的总收率）建立了高效合成（±）-yezo 'otogirin C的途径。天然产物及其结构类似物对几种人类癌细胞具有抗肿瘤活性，并在不同阶段阻滞细胞周期。
A systematic study of the biomimetic pathways to yezo’otogirin C under aerobic and anaerobic conditions has been investigated, and both are found to be feasible pathways to the natural product depending on the physiological conditions. Because of the lower activation energy, the aerobic process would be more favorable when the in vivo oxygen level is high. In the course of this study, a highly efficient synthetic route to (±)-yezo’otogirin C has been established in four steps (31% overall yield) from a readily available compound without using any protecting groups. The natural product and its structural analogues exhibited antitumor activities against several human cancer cell lines and appeared to arrest cell cycles in different phases.