4,5,6-trimethoxycoumaranone | 204648-48-6

• 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: 4,5,6-trimethoxycoumaranone
• 英文别名: 4,5,6-trimethoxy-1-benzofuran-3-one
• CAS: 204648-48-6
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: CDGWQGPJQZDZLA-UHFFFAOYSA-N

物化性质

• 熔点：
  142.5-143.5 °C
• 沸点：
  382.4±42.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5,6-trimethoxycoumaranone 在 potassium cyanide 、 aluminum oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 4’,5,6,7-四甲氧基黄酮
  参考文献：
  名称：

  The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents

  摘要：

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.003
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 PPA 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4,5,6-trimethoxycoumaranone
  参考文献：
  名称：

  The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents

  摘要：

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.003

文献信息

• Synthesis and Insect Antifeedant Activity of Aurones against <i>Spodoptera litura</i> Larvae
  作者：Masanori Morimoto、Hiromi Fukumoto、Toki Nozoe、Ai Hagiwara、Koichiro Komai

  DOI：10.1021/jf062562t

  日期：2007.2.1

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.
• Design, synthesis and evaluation of dihydro-1 <i>H</i> -indene derivatives as novel tubulin polymerisation inhibitors with anti-angiogenic and antitumor potency
  作者：Shengtao Xu、Yijun Sun、Peng Wang、Yuchen Tan、Lei Shi、Jian Chen

  DOI：10.1080/14756366.2023.2247579

  日期：2023.12.31
• The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents
  作者：Nicholas J. Lawrence、David Rennison、Alan T. McGown、John A. Hadfield

  DOI：10.1016/j.bmcl.2003.07.003

  日期：2003.11

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.