(1S,2S,5R,8S,10S,11R,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.15,8.01,11.02,8]octadecane-7,9,16-trione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,5R,8S,10S,11R,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.15,8.01,11.02,8]octadecane-7,9,16-trione
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: LWOAEMJVKDXOEG-GVWZTLLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  毛萼乙素 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到(1S,2S,5R,8S,10S,11R,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.15,8.01,11.02,8]octadecane-7,9,16-trione
  参考文献：
  名称：

  Synthesis and cytotoxicity of some new eriocalyxin B derivatives

  摘要：

  Eriocalyxin B (1) was regarded as the promising candidate for new anticancer agent because of its potent activity and novel mechanism of action. Systematic modifications of 1 were done, and nineteen derivatives were synthesized and their cytotoxicities against five tumor cell lines were evaluated. The structure-activity relationship (SAR) of 1 confirmed that the alpha,beta-unsaturated ketone moieties in ring A and D are the leading active sites; the 7,20-epoxy moiety, OH-6 and OH-7 play an important role in keeping the cytotoxicity. The 6,7-seco derivative 19 had remarkable activity while derivative 20 oxidized from 19 was completely inactive, which suggested that the carboxyl group could destroy the cytoxicity of 20 despite the presence of alpha,beta-unsaturated ketone moiety. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.11.004

文献信息

• Total Synthesis-Enabled Systematic Structure–Activity Relationship Study for Development of a Bioactive Alkyne-Tagged Derivative of Neolaxiflorin L
  作者：Mengxun Zhang、Magnolia Muk-Lan Lee、Weijian Ye、Wing-Yan Wong、Brandon Dow Chan、Sibao Chen、Lizhi Zhu、William Chi-Shing Tai、Chi-Sing Lee

  DOI：10.1021/acs.joc.9b00748

  日期：2019.6.7

  20-epoxy-ent-kuarenoid and was found to be a promising anticancer drug candidate in our previous study. In order to study its structure–activity relationship (SAR), a diversity-oriented synthetic route toward two libraries of (±)-NL analogs, including analogs containing different functionalities in the same 7,20-epoxy-ent-kuarene skeleton and analogs with skeletal changes, has been developed. The results of

  Neolaxiflorin L（NL）是一种低丰度香茶7,20 -环氧耳鼻喉科-kuarenoid和被认为是一个有前途的在我们以前的研究抗癌候选药物。为了研究其结构-活性关系（SAR），朝向（±）-NL类似物两个库，其中包括含在相同的7,20-环氧不同功能类似物一个多样性导向合成路线ENT -kuarene骨架和类似物随着骨骼的变化，已经被开发出来。这种具有全合成功能的SAR的结果成功产生了具有生物活性的炔烃标记的NL衍生物，这可能是蛋白质组学研究的有用探针。

表征谱图