3,3'-[3-(2-hydroxyphenyl)-3-oxopropane-1,1-diyl]bis(4-hydroxy-2H-chromen-2-one) | 1609702-43-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3'-[3-(2-hydroxyphenyl)-3-oxopropane-1,1-diyl]bis(4-hydroxy-2H-chromen-2-one)
• 英文别名: 4-Hydroxy-3-[1-(4-hydroxy-2-oxochromen-3-yl)-3-(2-hydroxyphenyl)-3-oxopropyl]chromen-2-one；4-hydroxy-3-[1-(4-hydroxy-2-oxochromen-3-yl)-3-(2-hydroxyphenyl)-3-oxopropyl]chromen-2-one
• CAS: 1609702-43-3
• 化学式: C₂₇H₁₈O₈
• 分子量: 470.435
• InChiKey: JEMYMCJFCCPZCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  色酮-3-甲酸 、 4-羟基香豆素 在 4-吡咯烷基吡啶 作用下， 以 氯仿 为溶剂， 以72%的产率得到3,3'-[3-(2-hydroxyphenyl)-3-oxopropane-1,1-diyl]bis(4-hydroxy-2H-chromen-2-one)
  参考文献：
  名称：

  Bis(4-hydroxy-2H-chromen-2-one): Synthesis and effects on leukemic cell lines proliferation and NF-κB regulation

  摘要：

  Synthesis of the bis-4-hydroxycoumarin-type compound, 3,3'-[3-(2-hydroxyphenyl)-3-oxopropane-1,1-diyl] bis(4-hydroxy-2H-chromen-2-one), was performed by two alternative pathways, either involving a basic organocatalyzed 1,4-conjugate addition tandem reaction of 4-hydroxycoumarin on chromone-3-carboxylic acid, or a double condensation of 4-hydroxycoumarin on omega-formyl-2'-hydroxyacetophenone. The anti-proliferative effects of the bis-4-hydroxycoumarin-type compound on human K-562 (chronic myeloid leukaemia) and JURKAT (acute T-cell leukaemia) cell lines using trypan blue staining, as well as its involvement in nuclear factor-kappa B (NF-kappa B) regulation analyzed by luciferase reporter gene assay, gene expression analysis and western blots were analysed. This compound inhibited TNF alpha-induced NF-kappa B activation in K-562 (IC50 17.5 mu M) and JURKAT (IC50 19.0 mu M) cell lines, after 8 h of incubation. Interestingly, it exerted mainly cytostatic effects at low doses on both cell lines tested, whereas it decreased JURKAT cell viability starting at 50 mu M from 24 h of treatment. Importantly, it did not affect the viability of peripheral blood mononuclear cells (PBMCs) from healthy donors, even at concentrations above 100 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.046