1-hydroxy-3-(methoxymethoxy)-5,6-bis((2-methylbut-3-en-2-yl)oxy)-9H-xanthen-9-one | 951243-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-hydroxy-3-(methoxymethoxy)-5,6-bis((2-methylbut-3-en-2-yl)oxy)-9H-xanthen-9-one
• 英文别名: 1-Hydroxy-3-(methoxymethoxy)-5,6-bis(2-methylbut-3-en-2-yloxy)xanthen-9-one
• CAS: 951243-20-2
• 化学式: C₂₅H₂₈O₇
• 分子量: 440.493
• InChiKey: PDYKEGQRDXINII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-(methoxymethoxy)-5,6-bis((2-methylbut-3-en-2-yl)oxy)-9H-xanthen-9-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到
  参考文献：
  名称：

  Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents

  摘要：

  甘宝酸（GA）是一种特殊的藤黄属黄酮类化合物，因其显著的生物活性和独特的结构而备受关注。为了进一步探究其结构与活性的关系，我们制备了七种新型氧杂笼型加西黄酮，并首次在笼型支架中 B 环的 C-2 位和预烯基的 C-21/22 或 C-23 位上进行了变化。一些化合物在不同的癌细胞系中表现出很强的抗癌活性。特别是化合物 8 比 GA 对 A549 细胞系表现出更强的细胞毒活性和更好的选择性。通过观察形态学变化和Annexin-V/PI双染色检测，确定氧杂笼黄酮8是一种A549细胞凋亡诱导剂。此外，还讨论了这些新类似物的结构-活性关系。

  DOI：

  10.1071/ch14328
• 作为产物：
  描述：

  在 10 percent palladium on barium sulphate 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到1-hydroxy-3-(methoxymethoxy)-5,6-bis((2-methylbut-3-en-2-yl)oxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents

  摘要：

  甘宝酸（GA）是一种特殊的藤黄属黄酮类化合物，因其显著的生物活性和独特的结构而备受关注。为了进一步探究其结构与活性的关系，我们制备了七种新型氧杂笼型加西黄酮，并首次在笼型支架中 B 环的 C-2 位和预烯基的 C-21/22 或 C-23 位上进行了变化。一些化合物在不同的癌细胞系中表现出很强的抗癌活性。特别是化合物 8 比 GA 对 A549 细胞系表现出更强的细胞毒活性和更好的选择性。通过观察形态学变化和Annexin-V/PI双染色检测，确定氧杂笼黄酮8是一种A549细胞凋亡诱导剂。此外，还讨论了这些新类似物的结构-活性关系。

  DOI：

  10.1071/ch14328

文献信息

• A novel and efficient route to the construction of the 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold
  作者：Nian-Guang Li、Jin-Xin Wang、Xiao-Rong Liu、Chang-Jun Lin、Qi-Dong You、Qing-Long Guo

  DOI：10.1016/j.tetlet.2007.07.005

  日期：2007.9

  A short and efficient route to the synthesis of 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold 12 in good yield is reported. Essential to the synthesis was the implementation of selective protection of the catechol system in xanthone 2 with Ph2CCl2 and MOM groups. Subsequently, a biomimetic tandem Claisen/Diels–Alder reaction occurred to produce the desired tricyclic scaffold 11a as a single isomer. A

  据报道，一种短而有效的途径以高收率合成了4-氧杂-三环[4.3.1.0]癸烷-2-酮骨架12。合成必不可少的是在具有Ph 2 CCl 2和MOM基团的蒽酮2中实现邻苯二酚系统的选择性保护。随后，发生了仿生串联的Claisen / Diels-Alder反应，生成了所需的三环骨架11a，为单一异构体。还提出了该转换的优良区域的合理化和立体选择性的建议。
• Synthesis, structure-activity relationship and in vitro pharmacodynamics of A-ring modified caged xanthones in a preclinical model of inflammatory breast cancer
  作者：Oraphin Chantarasriwong、Andrew T. Milcarek、Theodore Habarth Morales、Aspen L. Settle、Celso O. Rezende、Bashayer D. Althufairi、Maria A. Theodoraki、Mary L. Alpaugh、Emmanuel A. Theodorakis

  DOI：10.1016/j.ejmech.2019.02.047

  日期：2019.4

  Inflammatory breast cancer (IBC) is a highly metastatic, lethal form of breast cancer that lacks targeted therapeutic strategies. Inspired by the promising cytotoxicity of gambogic acid and related caged xanthones in spheroids(MARY-X), an in vitro preclinical IBC model, we constructed a library of synthetic analogs and performed structure-activity relationship studies. The studies revealed that functionalizing the A-ring of the caged xanthone framework can significantly affect potency. Specifically, introduction of hydroxyl or fluorine groups at discrete positions of the A-ring leads to enhanced cytotoxicity at sub-micromolar concentrations. These compounds induce complete dissolution of spheroids(MARY-X) with subsequent apoptosis of both the peripherally- and centrally-located cells, proliferative and quiescent-prone (e.g. hypoxic), respectively. These results highlight the structural flexibility and pharmacological potential of the caged xanthone motif for the design of IBC-targeting therapeutics. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Synthesis and Bioevaluation of Novel Oxa-Caged Garcinia Xanthones as Anti-Tumour Agents
  作者：Guangqiang Miao、Junhai Ma、Kan Yang、Zhipeng Huang、Qinlan Gu、Yanjie Wang、Qinglong Guo、Qidong You、Jinxin Wang

  DOI：10.1071/ch14328

  日期：——

  Gambogic acid (GA), a special category of Garcinia xanthones, has attracted great attention owing to its striking bioactivities and unique structure. To further explore its structure–activity relationship, we prepared seven novel oxa-caged Garcinia xanthones that were for the first time varied at the C-2 position of B ring and at the C-21/22 or C-23 position of the prenyl group in the caged scaffold. Some compounds exhibited strong anti-proliferation activities in different cancer cell lines. Particularly, compound 8 showed more potent cytotoxic activity and better selectivity towards the A549 cell line than GA. Oxa-caged xanthones 8 was identified as an A549 cell apoptosis inducer through observations of morphological changes and Annexin-V/PI double-staining assay. Additionally, the structure–activity relationships of these new analogues were discussed.

  甘宝酸（GA）是一种特殊的藤黄属黄酮类化合物，因其显著的生物活性和独特的结构而备受关注。为了进一步探究其结构与活性的关系，我们制备了七种新型氧杂笼型加西黄酮，并首次在笼型支架中 B 环的 C-2 位和预烯基的 C-21/22 或 C-23 位上进行了变化。一些化合物在不同的癌细胞系中表现出很强的抗癌活性。特别是化合物 8 比 GA 对 A549 细胞系表现出更强的细胞毒活性和更好的选择性。通过观察形态学变化和Annexin-V/PI双染色检测，确定氧杂笼黄酮8是一种A549细胞凋亡诱导剂。此外，还讨论了这些新类似物的结构-活性关系。