IBS_STOCK1N-22287 | 314745-43-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: IBS_STOCK1N-22287
• 英文别名: 5-Hydroxy-2-phenyl-7-(3-phenylprop-2-enoxy)chromen-4-one
• CAS: 314745-43-2
• 化学式: C₂₄H₁₈O₄
• 分子量: 370.405
• InChiKey: VXRQEDMGPFPQNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  IBS_STOCK1N-22287 在 N,N-二乙基苯胺 作用下， 反应 3.0h， 生成 5,7-dihydroxy-8-(1-phenyl-2-propenyl)flavone
  参考文献：
  名称：

  Upregulation of both heme oxygenase-1 and ATPase inhibitory factor 1 renders tumoricidal activity by synthetic flavonoids via depleting cellular ATP

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.08.055
• 作为产物：
  描述：

  白杨素 、 ethyl cinnamylcarbonate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 IBS_STOCK1N-22287
  参考文献：
  名称：

  Upregulation of both heme oxygenase-1 and ATPase inhibitory factor 1 renders tumoricidal activity by synthetic flavonoids via depleting cellular ATP

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.08.055

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.