acetolupuphenone | 35049-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: acetolupuphenone
• 英文别名: 2-Acetyl-3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one；2-acetyl-3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• CAS: 35049-58-2
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: OFVIRHKTSPGAQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetolupuphenone 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到
  参考文献：
  名称：

  蛇麻酮的便捷合成及其衍生化为 2,8-7H-二氢色烯-7-酮

  摘要：

  一种合成 β 酸或蛇麻酮的方便且改进的方法，已知这些酸或蛇麻酮具有e.克。抗癌、抗炎、抗氧化和抗菌活性已被开发成功。这些复杂结构进一步衍生为相应的二氢色烯-7-酮，包括天然产物马丘酮，以简化其分析并确认其分子结构。除了实用和安全的实验室程序之外，与这种新方法相关的优点包括使用水作为溶剂以及从乙腈中直接结晶羽扇豆酮，使我们的策略与现有方法相比更加有效和良性。

  DOI：

  10.1002/open.202000008
• 作为产物：
  描述：

  间苯三酚 在 aluminum (III) chloride 、 氨 作用下， 以 乙醚 、 硝基甲烷 、 二氯甲烷 为溶剂， 生成 acetolupuphenone
  参考文献：
  名称：

  The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells

  摘要：

  The beta-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231.The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the alpha-substituent R-1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.11.011

文献信息

• Expedient Synthesis of Lupulones and Their Derivatization to 2,8‐7 <i>H</i> ‐Dihydrochromen‐7‐ones
  作者：Lena Decuyper、Gurkirat Kaur、Charlotte Versyck、Eline Blondeel、Yves Depetter、Kristof Van Hecke、Matthias D'hooghe

  DOI：10.1002/open.202000008

  日期：2020.4

  A convenient and improved method for the synthesis of beta acids or lupulones, which are known to possess e. g. anti‐cancer, anti‐inflammatory, anti‐oxidative and antimicrobial activity, has been developed successfully. Further derivatization of these complex structures to the corresponding dihydrochromen‐7‐ones, including the natural product machuone, was realized to simplify their analysis and to

  一种合成 β 酸或蛇麻酮的方便且改进的方法，已知这些酸或蛇麻酮具有e.克。抗癌、抗炎、抗氧化和抗菌活性已被开发成功。这些复杂结构进一步衍生为相应的二氢色烯-7-酮，包括天然产物马丘酮，以简化其分析并确认其分子结构。除了实用和安全的实验室程序之外，与这种新方法相关的优点包括使用水作为溶剂以及从乙腈中直接结晶羽扇豆酮，使我们的策略与现有方法相比更加有效和良性。
• The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells
  作者：Elizabeth Tyrrell、Roland Archer、Matt Tucknott、Kay Colston、Grisha Pirianov、Dharahana Ramanthan、Rajdeep Dhillon、Alex Sinclair、G.A. Skinner

  DOI：10.1016/j.phytol.2011.11.011

  日期：2012.3

  The beta-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231.The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the alpha-substituent R-1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.