结香素 | 120028-43-5

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 结香素
• 中文别名: 2H-1-苯并吡喃-2-酮,7-羟基-3-[(2-羰基-2H-1-苯并吡喃-7-基)氧代]-
• 英文名称: edgeworin
• 英文别名: 7-hydroxy-3-(2-oxochromen-7-yl)oxychromen-2-one
• CAS: 120028-43-5
• 化学式: C₁₈H₁₀O₆
• 分子量: 322.274
• InChiKey: WNLKKLCKMRDNHF-UHFFFAOYSA-N

物化性质

• 熔点：
  284-296℃
• 沸点：
  617.0±55.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  结香素 、 乙酸酐 以 吡啶 为溶剂， 以0.11 g的产率得到Acetic acid 2-oxo-3-(2-oxo-2H-chromen-7-yloxy)-2H-chromen-7-yl ester
  参考文献：
  名称：

  来自Edgeworthia chrysantha的香豆素☆

  摘要：

  摘要 从 Edgeworthia chrysantha ( E. papyrifera ) 的根和茎中分离到了两种新的香豆素，edgeworin 和 edgeworoside A，其结构确定为 3-(7-coumarinyloxy)-7-hydroxycoumarin 和 3-(7-coumarinyloxy)- 8-(7-羟基香豆素-8-基)-7-α-1-鼠李糖基氧基香豆素。

  DOI：

  10.1016/0031-9422(89)85042-3
• 作为产物：
  描述：

  3-(7-coumarinyloxy)-4-bromo-7-methoxycoumarin 在 盐酸 、 三氯化铝 、 锌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 49.5h， 生成 结香素
  参考文献：
  名称：

  New Total Synthesis of O‐Methyledgeworin and Edgeworin

  摘要：

  Upon thermal condensation of diethyl (coumarinyl-7-oxy)malonate with O-methyl-resorcine, the corresponding bis[coumarinyl]ether, 4-hydroxy-O-methyledgeworin is obtained in good yield. This leads to 4-bromo-O-methyledgeworin, O-methyledgeworin, and edgeworin.

  DOI：

  10.1080/00397910500406088

文献信息

• Inhibitors of DNA polymerase β: Activity and mechanism
  作者：Zhijie Gao、David J. Maloney、Larisa M. Dedkova、Sidney M. Hecht

  DOI：10.1016/j.bmc.2008.02.071

  日期：2008.4

  Bioassay-guided fractionation of extracts prepared from Couepia polyandra and Edgeworthia gardneri resulted in the isolation of the DNA polymerase beta (pol beta) inhibitors oleanolic acid (1), edgeworin (2), betulinic acid (3), and stigmasterol (4). Study of these pol b inhibitors revealed that three of them inhibited both the lyase and polymerase activities of DNA polymerase beta, while stigmasterol inhibited only the lyase activity. Further investigation indicated that the four inhibitors had substantially different effects on the DNA-pol beta binary complex that is believed to be an obligatory intermediate in the lyase reaction. It was found that the inhibitors potentiated the inhibitory action of the anticancer drug bleomycin in cultured A549 cells, without any influence on the expression of pol beta in the cells. The results of the unscheduled DNA synthesis assay support the thesis that the potentiation of bleomycin cytotoxicity by DNA pol beta inhibitors was a result of an inhibition of DNA repair synthesis. (C) 2008 Elsevier Ltd. All rights reserved.
• BABA, KIMIYE;TABATA, YUKO;TANIGUTI, MASAHIKO;KOZAWA, MITSUGI, PHYTOCHEMISTRY, 28,(1989) N 1, C. 221-225
  作者：BABA, KIMIYE、TABATA, YUKO、TANIGUTI, MASAHIKO、KOZAWA, MITSUGI

  DOI：——

  日期：——
• METHODS FOR DIRECTING DIFFERENTIATION OF CLONOGENIC NEURAL STEM CELLS WITH COUMARINS
  申请人：HE Cheng

  公开号：US20090170930A1

  公开（公告）日：2009-07-02

  A method for promoting differentiation of clonogenic neural stem cells (NSCs), comprising administering to a patient in the need of such promoting a coumarin compound represented by formula I or by formula II. The representative coumarin compounds include 7-hydroxycoumarin, daphnoretin, scopoletin, edgeworin, aesculetin and esculetin-6-β-D-glucopyranoside. The coumarin compounds showed significant activity of directing the differentiation of NSCs in pharmacological test and thereof could be used to prepare drugs to direct NSCs differentiated to oligodendrocyte progenitor cells (OPCs) for the treatment of demyelinating diseases or spinal cord injury. The drug could be a pure coumarin compound or a pharmaceutical composition comprising a therapeutical dose of a coumarin compound as active ingredients and a pharmaceutically-acceptable carrier. The content of the active ingredients in the pharmaceutical composition is between 0.1% and 99.5% by weight.
• Coumarins from Edgeworthia chrysantha☆
  作者：Kimiye Baba、Yuko Tabata、Masahiko Taniguti、Mitsugi Kozawa

  DOI：10.1016/0031-9422(89)85042-3

  日期：——

  Abstract Two new coumarins, edgeworin and edgeworoside A, were isolated from the root and stem of Edgeworthia chrysantha ( E. papyrifera ) and their structures determined as 3-(7-coumarinyloxy)-7-hydroxycoumarin and 3-(7-coumarinyloxy)-8-(7-hydroxycoumarin-8-yl)-7-α- l -rhamnopyranosyloxycoumarin.

  摘要 从 Edgeworthia chrysantha ( E. papyrifera ) 的根和茎中分离到了两种新的香豆素，edgeworin 和 edgeworoside A，其结构确定为 3-(7-coumarinyloxy)-7-hydroxycoumarin 和 3-(7-coumarinyloxy)- 8-(7-羟基香豆素-8-基)-7-α-1-鼠李糖基氧基香豆素。
• New Total Synthesis of O‐Methyledgeworin and Edgeworin
  作者：B. Serge Kirkiacharian、Marie Brillard

  DOI：10.1080/00397910500406088

  日期：2006.3.1

  Upon thermal condensation of diethyl (coumarinyl-7-oxy)malonate with O-methyl-resorcine, the corresponding bis[coumarinyl]ether, 4-hydroxy-O-methyledgeworin is obtained in good yield. This leads to 4-bromo-O-methyledgeworin, O-methyledgeworin, and edgeworin.