5,7-dihydroxy-3-(3',4'-dihydroxyphenyl)-2H-1-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,7-dihydroxy-3-(3',4'-dihydroxyphenyl)-2H-1-chromen-2-one
• 英文别名: 5,7-dihydroxy-3-(3',4'-dihydroxyphenyl)coumarin；3-(3,4-dihydroxyphenyl)-5,7-dihydroxycoumarin；5,7,3',4'-tetrahydroxy-3-phenylcoumarin；3-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-coumarin；3-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-cumarin；3-(3,4-Dihydroxyphenyl)-5,7-dihydroxychromen-2-one
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: UGXNCLFMWOIXDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2(3),9(10),16(17),23(24)-tetra(2,3-dihydro-1H-inden-5-yloxy)phthalocyaninatotitanium(IV) oxide 、 5,7-dihydroxy-3-(3',4'-dihydroxyphenyl)-2H-1-chromen-2-one 以88.5%的产率得到3-(3-(3,4-dioxyphenyl)-5,7-dihydroxycoumarino)-2(3),9(10),16(17),23(24)-tetra(2,3-dihydro-1H-inden-5-yloxy)phthalocyaninatotitanium
  参考文献：
  名称：

  Synthesis, characterization and dielectric properties of novel axial coumarin-substituted titanium(IV) phthalocyanines

  摘要：

  The oxotitanium(IV) phthalocyanine (2) and axial coumarin-substituted derivatives (5 and 6) have been synthesized, and characterized by IR, UV-Vis, fluorescence, H-1 NMR, MALDI-TOF mass spectrometry and elemental analysis. It was observed that the reaction of novel oxotitanium(IV) phthalocyanine with orthodihyroxycoumarin compounds gives its derivatives, substituted by coumarin at the axial position. The electronic and interface state density properties of the Ag/Pc/p-Si diodes have been investigated by current-voltage (I-V) and conductance-frequency-voltage (G-omega-V) methods. It was found that, the conduction mechanism of the diodes is controlled by the thermoionic emission mechanism. From the analysis of frequency, omega, dependence of electrical conductivity, sigma(ac), it was found that the sigma(ac) obeys the power law given by sigma(ac), = sigma(0)w(s). The interface state density of the diodes were determined from (G/omega)-omega plots. It was found that the kind of substitution affects both the interface and omega electrical properties of the phthalocyanine complexes considerably. The obtained results show that the Ag/6/p-Si heterojunction is a good candidate for the electronic device applications. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.09.055
• 作为产物：
  描述：

  3-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-2-one 在 氢碘酸 作用下， 生成 5,7-dihydroxy-3-(3',4'-dihydroxyphenyl)-2H-1-chromen-2-one
  参考文献：
  名称：

  Baker, Journal of the Chemical Society, 1929, p. 1596

  摘要：

  DOI：

文献信息

• <i>In Vitro</i>Inhibition of Human Placental Glutathione<i>S</i>-Transferase by 3-Arylcoumarin Derivatives
  作者：Mustafa Muhlis Alparslan、Özkan Danış

  DOI：10.1002/ardp.201500151

  日期：2015.9

  investigated the inhibitory effects of differently substituted 3‐arylcoumarin derivatives on human placental GST, identified as GSTP1‐1, using 1‐chloro‐2,4‐dinitrobenzene as a substrate. A known potent inhibitor of GST, ethacrynic acid was used as a positive control. Among the tested compounds, 6,7‐dihydroxy substituted coumarin derivatives exhibited the highest inhibitory activity (IC50 = 13.50–20.83 μM). These

  谷胱甘肽 S 转移酶 (EC: 2.5.1.18, GSTs) 是 II 相解毒酶，可催化各种亲电子化合物与谷胱甘肽 (GSH) 的结合，因此通常会产生反应性较低且水溶性更好的化合物。然而，有证据表明 GSTs，尤其是 GSTP1 的表达升高与肿瘤细胞对化疗药物的抗性有关。在这项研究中，我们合成并研究了不同取代的 3-芳基香豆素衍生物对人胎盘 GST 的抑制作用，鉴定为 GSTP1-1，使用 1-氯-2,4-二硝基苯作为底物。已知的 GST 强效抑制剂 ethacrynic 酸用作阳性对照。在测试的化合物中，6,7-二羟基取代的香豆素衍生物表现出最高的抑制活性（IC50 = 13.50–20.83 μM）。
• Synthesis of selected 3- and 4-arylcoumarin derivatives and evaluation as potent antioxidants
  作者：Ozkan Danis、Serap Demir、Cihan Gunduz、Mustafa Muhlis Alparslan、Selcuk Altun、Basak Yuce-Dursun

  DOI：10.1007/s11164-016-2445-7

  日期：2016.6

  radical scavenging, with better performance than known antioxidants in DPPH and metal-chelating assays. In addition, the cupric-reducing antioxidant capacity and ferric-reducing antioxidant power of the synthesized compounds were investigated for antioxidant activity. Among them, 5g , h and 6a , b showed significantly better Trolox equivalent antioxidant capacity (TEAC) than standard compounds. The results

  合成了一系列羟基，甲氧基和乙酰氧基取代的3-和4-芳基香豆素。筛选所有标题化合物的抗氧化能力，清除1,1-二苯基-1-吡啶并肼基（DPPH）自由基的能力以及螯合铁离子的能力。此外，使用分子特性预测评估所有衍生物，并使用Molinspiration评估药物相似性。结果发现，所有研究的衍生物均符合Lipinski关于药物相似性的5条规则，因此有可能进一步研究。在 邻位 具有两个羟基（例如 4h ， 5b ， h 和 6a）的 3-或4-芳香豆素 在自由基清除中具有显着的半最大有效浓度（EC 50），其性能优于已知的抗氧化剂。此外，研究了合成化合物的还原铜的抗氧化能力和还原铁的抗氧化能力。其中 5g ， h 和 6a ， b 与标准化合物相比，具有明显更好的Trolox等效抗氧化能力（TEAC）。结果表明，在芳族香豆素结构的苯并吡喃酮环的6-位和7-位具有二羟基的化合物是该系列中最活跃的抗氧化剂