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Oscillatoxin E and Its C7 Epimer Show Distinct Growth Inhibition Profiles against Several Cancer Cell Lines
Heterocycles ( IF 0.6 ) Pub Date : 2021-09-14 , DOI: 10.3987/com-21-14538
Yusuke Hanaki , Yusuke Araki , Toshio Nishikawa , Ryo C. Yanagita

Oscillatoxins (OTXs) are naturally occurring polyketides produced by some marine cyanobacteria. We have recently reported the total synthesis and in vitro biological activities of OTX-D, E, and F. Their spiro-ether structure was synthesized with an intramolecular Mukaiyama aldol reaction as a key step. Although the desired isomer was stereoselectively obtained, some amount of its C7 epimer was also produced as a byproduct. Using the C7 epimer, we investigated the effect of stereochemistry at the spiro-center of OTX-E (1) on its antiproliferative activity against several cancer cell lines. Growth inhibitory activity of 1 and its C7 epimer 2 was not strong, but they showed different efficacy profiles from each other. This result suggests that our synthetic method for OTXs would contribute to not only total synthesis of natural products but also to construction of chemical libraries containing unique biologically active compounds.

中文翻译:

Oscillatoxin E 及其 C7 差向异构体对几种癌细胞系显示出不同的生长抑制特性

Oscillatoxins (OTXs) 是由一些海洋蓝藻产生的天然聚酮化合物。我们最近报道了OTX-D、E 和 F的全合成和体外生物活性。它们的螺醚结构是通过分子内向山羟醛反应合成的,作为关键步骤。尽管立体选择性地获得了所需的异构体,但也产生了一些其 C7 差向异构体作为副产物。使用 C7 差向异构体,我们研究了 OTX-E ( 1 )螺旋中心的立体化学对其针对几种癌细胞系的抗增殖活性的影响。1及其C7差向异构体2的生长抑制活性不强,但它们显示出彼此不同的功效特征。这一结果表明,我们的 OTX 合成方法不仅有助于天然产物的全合成,而且有助于构建包含独特生物活性化合物的化学库。
更新日期:2021-09-14
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