ω-formyl-2'-hydroxyacetophenone | 87059-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ω-formyl-2'-hydroxyacetophenone
• 英文别名: 1-(2-hydroxyphenyl)-propan-1,3-dione；(Z)-3-hydroxy-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 87059-79-8
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: INSPSAHTPWMTAG-WAYWQWQTSA-N

物化性质

• 沸点：
  318.3±42.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基香豆素 、 ω-formyl-2'-hydroxyacetophenone 在 4-吡咯烷基吡啶 作用下， 以 氯仿 为溶剂， 以83%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
• 作为产物：
  描述：

  2-羟基-2,3-二氢色烯-4-酮 以 氘代氯仿 为溶剂， 反应 200.0h， 以2%的产率得到2-(formylacetyl)phenol
  参考文献：
  名称：

  Examination of the ring-chain isomerism of 2-hydroxy-chromanones with 1H NMR spectroscopy

  摘要：

  DOI：

  10.1016/s0040-4039(01)81693-2

文献信息

• Zsuga, M.; Szabo, V.; Korodi, F., Acta Chimica Hungarica, 1983, vol. 112, # 1, p. 111 - 119
  作者：Zsuga, M.、Szabo, V.、Korodi, F.

  DOI：——

  日期：——
• Examination of the ring-chain isomerism of 2-hydroxy-chromanones with 1H NMR spectroscopy
  作者：János Borbély、Vince Szabó

  DOI：10.1016/s0040-4039(01)81693-2

  日期：1984.1
• Bis(4-hydroxy-2H-chromen-2-one): Synthesis and effects on leukemic cell lines proliferation and NF-κB regulation
  作者：Oualid Talhi、Michael Schnekenburger、Jana Panning、Diana G.C. Pinto、José A. Fernandes、Filipe A. Almeida Paz、Claus Jacob、Marc Diederich、Artur M.S. Silva

  DOI：10.1016/j.bmc.2014.03.046

  日期：2014.6

  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.