(Z)-5-hydroxy-2-benzylidene-benzofuran-3(2H)-one | 1234351-38-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-5-hydroxy-2-benzylidene-benzofuran-3(2H)-one
• 英文别名: (Z)-2-benzylidene-5-hydroxybenzofuran-3(2H)-one；(Z)-5-hydroxy-2-benzylidene-benzofuran-3-one；2-benzylidene-5-hydroxybenzofuran-3(2H)-one；(2Z)-2-benzylidene-5-hydroxy-1-benzofuran-3-one
• CAS: 1234351-38-2
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: SHURXQGYCUNAOB-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-hydroxy-2-benzylidene-benzofuran-3(2H)-one 、 环氧氯丙烷 生成 (2Z)-2-benzylidene-6-(oxiran-2-ylmethoxy)-1-benzofuran-3-one
  参考文献：
  名称：

  WU, EDWIN S.

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[2-hydroxy-5-(methoxymethoxy)phenyl]-3-phenylprop-2-en-1-one 在 吡啶 、 盐酸 、 mercury(II) diacetate 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (Z)-5-hydroxy-2-benzylidene-benzofuran-3(2H)-one
  参考文献：
  名称：

  Ferrocenyl-Appended Aurone and Flavone: Which Possesses Higher Inhibitory Effects on DNA Oxidation and Radicals?

  摘要：

  The aim of the present work was to compare the antioxidative effect of the ferrocenyl-appended aurone with that of ferrocenyl-appended flavone; therefore, nine aurones together with the flavone-type analogues were synthesized by using chalcone as the reactant. The radical-scavenging property was evaluated by reacting with the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS'), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. The cytotoxicity was estimated by inhibiting 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that the introduction of the ferrocenyl group remarkably increased the radical-scavenging activities of aurone and flavone. Especially, the ferrocenyl group in flavones can quench radicals even in the absence of the phenolic hydroxyl group, while ferrocenyl-appended aurones can efficiently protect DNA against AAPH-induced oxidation. Therefore, the antioxidative effect was generated by the ferrocenyl group and enhanced by the electron-donating group attaching to the para-position of the ferrocenyl group. Introducing the ferrocenyl group into natural compounds may be a useful strategy for increasing the anticoddative effectiveness.

  DOI：

  10.1021/tx500405b

文献信息

• Investigation of Binding-Site Homology between Mushroom and Bacterial Tyrosinases by Using Aurones as Effectors
  作者：Romain Haudecoeur、Aurélie Gouron、Carole Dubois、Hélène Jamet、Mark Lightbody、Renaud Hardré、Anne Milet、Elisabetta Bergantino、Luigi Bubacco、Catherine Belle、Marius Réglier、Ahcène Boumendjel

  DOI：10.1002/cbic.201402003

  日期：2014.6.16

  A lighter future: Aurones have been identified as inhibitors of melanin biosynthesis. In this study, 24 aurones were evaluated on mushroom and bacterial tyrosinases (TyM and TyB). The compounds behaved as inhibitors, substrates, or activators of both enzymes. Our results highlight similarities and differences in behavior between TyM and TyB with the same set of molecules.

  更光明的未来： Aurones已被确定为黑色素生物合成的抑制剂。在这项研究中，对蘑菇和细菌酪氨酸酶（TyM和TyB）上的24种金质进行了评估。该化合物充当两种酶的抑制剂，底物或激活剂。我们的结果强调了在同一分子下TyM和TyB之间行为的异同。
• 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.
• Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines
  作者：Huimin Cheng、Lianwen Zhang、Yingxue Liu、Shaopeng Chen、Hao Cheng、Xin Lu、Zhuxia Zheng、Guo-Chun Zhou

  DOI：10.1016/j.ejmech.2010.09.061

  日期：2010.12

  A series of 4'-substituted 5-hydroxyaurone derivatives were synthesized and their inhibitory activities against the proliferation of endothelial cells and two cancer cell lines were studied. Some of these compounds functioned as potent inhibitors against the proliferation of endothelial cells and cancer cells but possessed much weaker cytotoxic activities against non-cancer cell line of CCC-HPF-1. It was demonstrated that two most active compounds 16 and 27 effectively inhibited in vitro endothelial cell motility and tube formation, which are basic properties of endothelial cells for angiogenesis. Moreover, 16 and 27 also showed significant activities against in vitro cancer cell invasion, indicating that they have potential to inhibit cancer metastasis. These composite results suggest that 4'-substituted 5-hydroxyaurone is indeed a candidate structural scaffold for anticancer agent targeting activated endothelial cells and fast-proliferating cancer cells. (C) 2010 Elsevier Masson SAS. All rights reserved.
• WU, EDWIN S.
  作者：WU, EDWIN S.

  DOI：——

  日期：——
• Ferrocenyl-Appended Aurone and Flavone: Which Possesses Higher Inhibitory Effects on DNA Oxidation and Radicals?
  作者：Jia-Feng Chen、Zai-Qun Liu

  DOI：10.1021/tx500405b

  日期：2015.3.16

  The aim of the present work was to compare the antioxidative effect of the ferrocenyl-appended aurone with that of ferrocenyl-appended flavone; therefore, nine aurones together with the flavone-type analogues were synthesized by using chalcone as the reactant. The radical-scavenging property was evaluated by reacting with the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS'), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. The cytotoxicity was estimated by inhibiting 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that the introduction of the ferrocenyl group remarkably increased the radical-scavenging activities of aurone and flavone. Especially, the ferrocenyl group in flavones can quench radicals even in the absence of the phenolic hydroxyl group, while ferrocenyl-appended aurones can efficiently protect DNA against AAPH-induced oxidation. Therefore, the antioxidative effect was generated by the ferrocenyl group and enhanced by the electron-donating group attaching to the para-position of the ferrocenyl group. Introducing the ferrocenyl group into natural compounds may be a useful strategy for increasing the anticoddative effectiveness.