(±)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]chrysin | 1616279-90-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (±)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]chrysin
• 英文别名: 5,7-Dihydroxy-8-[1-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-2-phenylchromen-4-one；5,7-dihydroxy-8-[1-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-2-phenylchromen-4-one
• CAS: 1616279-90-3
• 化学式: C₂₅H₂₀O₆
• 分子量: 416.43
• InChiKey: AIWFCANTYRMORD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白杨素 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三氯化硼 、 potassium carbonate 作用下， 以 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 (±)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]chrysin
  参考文献：
  名称：

  Gram-scale synthesis of anti-pancreatic flavonoids (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-chrysin and -galangin

  摘要：

  Gram-scale total synthesis of (+/-)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.057

文献信息

• Upregulation of both heme oxygenase-1 and ATPase inhibitory factor 1 renders tumoricidal activity by synthetic flavonoids via depleting cellular ATP
  作者：Phil Jun Lee、Iljin Shin、Seung-Yong Seo、Hyoungsu Kim、Hong Pyo Kim

  DOI：10.1016/j.bmcl.2014.08.055

  日期：2014.10

  Heme oxygenase-1 (HO-1) and ATPase inhibitory factor (ATPIF) 1 is often overexpressed in different types of cancer cells. Chrysin is a naturally-occurring flavonoid with antioxidant potentials, but also known to promote apoptosis. We have synthesized four chrysin derivatives and found compounds 1 and 4 remarkably upregulated the expression of HO-1, a cytoprotective enzyme. A robust expression of ATPIF1 was only seen in compound 4. Upregulation of both proteins triggers cell death in hydrogen peroxide-primed cells. Ten derivatives of compound 4 were synthesized and measured the expression of HO-1 and ATPIF1. Again, upregulation of both proteins by compound 8 killed the cells via apoptosis. To gain a physiological significance, we treated the synthetic flavonoids in colon cancer cells, HT29 and HCT116 cells and confirmed that overexpression of both HO-1 and ATPIF1 was critical for tumor cell death with an impaired mitochondrial energetics. It would provide a strategy for developing selective anti-tumor candidates. (C) 2014 Elsevier Ltd. All rights reserved.
• Gram-scale synthesis of anti-pancreatic flavonoids (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-chrysin and -galangin
  作者：Hyoungsu Kim、Donghee Lim、Iljin Shin、Dongjoo Lee

  DOI：10.1016/j.tet.2014.05.057

  日期：2014.8

  Gram-scale total synthesis of (+/-)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. (C) 2014 Elsevier Ltd. All rights reserved.