5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-benzo[b]furan-2-one | 27439-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-benzo[b]furan-2-one
• 英文别名: E-Marginalin；marginalin；(3E)-5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-1-benzofuran-2-one
• CAS: 27439-06-1
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: OBAXSLNBFZJCNP-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  亚精胺 、 5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-benzo[b]furan-2-one 以 二氯甲烷 为溶剂， 生成 N'-(3-aminopropyl)butane-1,4-diamine;(3E)-5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-1-benzofuran-2-one
  参考文献：
  名称：

  Barbier, Michel, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1990, vol. 45, # 10, p. 1455 - 1456

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 在 吗啉 、 氢氧化钾 、 吡啶盐酸盐 、 对甲苯磺酸 、 sulfur 、 三氯氧磷 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 50.0h， 生成 5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-benzo[b]furan-2-one
  参考文献：
  名称：

  异金龙：几何异构体的合成和立体化学分配

  摘要：

  在三个步骤中，首次通过苯并-2（3 H）-呋喃酮从取代的苯乙酮合成了一系列异金酮。分离了异金酮的几何异构体。E-和Z-异金龙的质子和碳NMR谱图的差异为区分这两种异构体提供了一种有用的方法。已合成了边缘dyscuscusalis的代谢物Marginalin，合成的E-异构体的光谱数据与天然产物的光谱数据非常吻合。通过超氧自由基（NBT）方法和异金龙12和13测定了异金龙的抗氧化活性 表现出优异的抗氧化活性。

  DOI：

  10.1016/j.tet.2006.08.048

文献信息

• Inhibitory activities against topoisomerase I and II by isoaurostatin derivatives and their structure–activity relationships
  作者：Keitarou Suzuki、Tadashi Okawara、Tatuya Higashijima、Kazumi Yokomizo、Tohru Mizushima、Masami Otsuka

  DOI：10.1016/j.bmcl.2005.02.052

  日期：2005.4

  A (IAS-A) isolated from Thermomonospora alba showed weak inhibition against topoisomerase (topo) I (IC(50)=307microM). To get more strong inhibition, derivatives of IAS-A were prepared and their structure-activity relationships against topo I and II were investigated. The addition of hydroxyl group on aromatic rings increased the activities, 3-(3,4,5-trihydroxybenzylidene)-5-hydroxy-3H-benzofuran-2-one

  从白热单孢菌中分离得到的异潮红素A（IAS-A）对拓扑异构酶（topo）I的抑制作用较弱（IC（50）= 307microM）。为了获得更强的抑制作用，制备了IAS-A衍生物，并研究了它们对topo I和II的构效关系。芳香环上羟基的添加增加了活性，3-（3,4,5-三羟基亚苄基）-5-羟基-3H-苯并呋喃-2-酮（IAS-9）表现出较强的抑制作用（IC（50）= 3microM ），同时增加羟基对多种癌细胞的生长抑制作用，而IAS-9表现出最强的抑制作用。与喜树碱和依托泊苷不同，IAS-9既不能稳定DNA-拓扑可裂解的复合物，也不能插入DNA中，并且非竞争性地抑制了topo I和II。
• Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
  作者：Chong-Yew Lee、Eng-Hui Chew、Mei-Lin Go

  DOI：10.1016/j.ejmech.2010.03.023

  日期：2010.7

  The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P) H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E-LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• Isoaurones: synthesis and stereochemical assignments of geometrical isomers
  作者：Somepalli Venkateswarlu、Gopala K. Panchagnula、Mothukuri Bala Guraiah、Gottumukkala V. Subbaraju

  DOI：10.1016/j.tet.2006.08.048

  日期：2006.10

  synthesized for the first time from substituted acetophenones via benzo-2(3H)-furanone in three steps. Geometrical isomers of the isoaurones were separated. The differences in the proton and carbon NMR spectra of the E- and Z-isoaurones afford a useful method for distinguishing between the two isomers. Marginalin, a metabolite of Dytiscus marginalis has been synthesized and the spectral data of the synthetic

  在三个步骤中，首次通过苯并-2（3 H）-呋喃酮从取代的苯乙酮合成了一系列异金酮。分离了异金酮的几何异构体。E-和Z-异金龙的质子和碳NMR谱图的差异为区分这两种异构体提供了一种有用的方法。已合成了边缘dyscuscusalis的代谢物Marginalin，合成的E-异构体的光谱数据与天然产物的光谱数据非常吻合。通过超氧自由基（NBT）方法和异金龙12和13测定了异金龙的抗氧化活性 表现出优异的抗氧化活性。
• Barbier, Michel, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1990, vol. 45, # 10, p. 1455 - 1456
  作者：Barbier, Michel

  DOI：——

  日期：——