(Z)-3'-hydroxy-5,6,7,4'-tetramethoxyaurone | 527750-39-6

• 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)-3'-hydroxy-5,6,7,4'-tetramethoxyaurone
• 英文别名: 2-[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-5,6,7-trimethoxy-benzofuran-3-one；(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-5,6,7-trimethoxy-1-benzofuran-3-one
• CAS: 527750-39-6
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: LZMHHIWFIGTABL-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-3'-hydroxy-5,6,7,4'-tetramethoxyaurone 在 potassium cyanide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以32%的产率得到2-(3-Hydroxy-4-methoxy-phenyl)-6,7,8-trimethoxy-chromen-4-one
  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：

  2,3,4-trimethoxyphenyl formate 在 甲醇 、 aluminum oxide 、 PPA 、 sodium methylate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (Z)-3'-hydroxy-5,6,7,4'-tetramethoxyaurone
  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

• Combretastatin a-4 derivatives having antineoplastic activity
  申请人：Lawrence James Nicholas

  公开号：US20050065213A1

  公开（公告）日：2005-03-24

  Compounds are disclosed that are designed to mimic the activity of combretastatin A-4 based on chalcone, aurone, or indanone structures, or involving benzoquinone or quinone rings. The anti-cancer activity of exemplified compounds is demonstrated in a range of in vitro and in vivo assays.

  公开了一些化合物，这些化合物是基于查尔酮、金合欢素或茚酮结构设计的，或涉及苯醌或醌环，旨在模仿紫杉醇A-4的活性。在一系列体外和体内试验中，展示了这些化合物的抗癌活性。
• Influence of the skeleton on the cytotoxicity of flavonoids
  作者：Guy Lewin、Geneviève Aubert、Sylviane Thoret、Joëlle Dubois、Thierry Cresteil

  DOI：10.1016/j.bmc.2011.12.038

  日期：2012.2

  Analogs of 3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone, a strongly cytotoxic and antimitotic semisynthetic flavone, were synthesized in the aurone, isoflavone and isoflavanone series. Comparison of the biological activity of these new compounds with the reference showed a potent cytotoxicity only in the flavone series. Influence of the hydroxy group (at C-5 in flavones, at C-4 in aurones) on the cytotoxicity, known to be favorable in flavones, was found to be detrimental in aurones. This observation was related to the hydrogen bonding formed with the carbonyl group, strong in the flavones, but of weak intensity in the aurones. (C) 2011 Elsevier Ltd. All rights reserved.
• COMBRETASTATIN A-4 DERIVATIVES HAVING ANTINEOPLASTIC ACTIVITY
  申请人：CANCER RESEARCH TECHNOLOGY LIMITED

  公开号：EP1444190A1

  公开（公告）日：2004-08-11
• [EN] COMBRETASTATIN A-4 DERIVATIVES HAVING ANTINEOPLASTIC ACTIVITY<br/>[FR] DERIVES DE LA COMBRETASTATINE A-4 A EFFETS ANTINEOPLASIQUES
  申请人：PATERSON INST FOR CANCER RES

  公开号：WO2003040077A1

  公开（公告）日：2003-05-15

  Compounds are disclosed that are designed to mimic the activity of combretastatin A-4 based on chalcone, aurone, or indanone structures, or involving benzoquinone or quinone rings. The anti-cancer activity of exemplified compounds is demonstrated in a range of in vitro and in vivo assays.
• 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.