(E)-2(3',4',5'-trimethoxyphenyl)-3-(4''-methoxyphenyl)prop-2-ene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2(3',4',5'-trimethoxyphenyl)-3-(4''-methoxyphenyl)prop-2-ene
• 英文别名: 1,2,3-trimethoxy-5-[(E)-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: MFQPNWHUDUDIHA-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 4-甲氧基苄基三苯基膦溴化盐 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以10%的产率得到1,2,3-Trimethoxy-5-[(Z)-2-(4-methoxy-phenyl)-1-methyl-vinyl]-benzene
  参考文献：
  名称：

  Synthesis and evaluation of double bond substituted combretastatins

  摘要：

  A series of cornbretastatins substituted with epoxides, amides and small alkyl groups has been synthesised and evaluated for cytotoxicity and their ability to inhibit the assembly of tubulin. The methyl and ethyl substituted phenols 36, 44 have shown potent antimitotic effects whilst exhibiting reduced cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.12.008

文献信息

• Substituted stilbenes and their reactions
  申请人：——

  公开号：US20040152629A1

  公开（公告）日：2004-08-05

  The present invention relates to stilbene and quinone compounds related to combretastatin A-4 and their use as anticancer compounds and prodrugs. The compounds include those with an alkyl group on the double bond of cis or trans-stilbenes, compounds with one or more (and preferably 2 or 3) alkyl group substituents on the stilbene A ring, compounds with an alkoxy group other than methoxy at position 3, 4, and/or 5 of the stilbene A ring, compounds (or prodrugs) in which BOC amino acid esters are formed with the phenolic hydroxyl at the 3-position of the B ring and compounds (or prodrugs) based on a benzoquinone B ring. The present invention further relates to the photochemical reactions of stilbene compounds, either the above compounds disclosed for the first time herein or compounds based on prior art stilbenes. These reactions include the photochemical release of an active form of the compound from a prodrug conjugate and the photochemical isomerisation of the compounds, especially from a trans to cis form of compounds. The reactions can be used alone or in combination to convert inactive or comparatively less active forms of the compounds to more active forms, thereby allowing the compounds to be selectively targeted, e.g. activating them at the site of a tumour.

  本发明涉及与康柏他定A-4相关的stilbene和quinone化合物及其作为抗癌化合物和前药的用途。这些化合物包括那些在顺式或反式stilbenes的双键上带有烷基的化合物，带有一个或多个（最好是2个或3个）烷基基团取代物的stilbene A环上的化合物，stilbene A环的3、4和/或5位置带有非甲氧基的烷氧基的化合物，以及在B环的3位的酚羟基形成BOC氨基酸酯的化合物（或前药）和基于苯醌B环的化合物（或前药）。本发明还涉及stilbene化合物的光化学反应，无论是本文首次披露的上述化合物还是基于先前技术的stilbenes的化合物。这些反应包括从前药共轭物中光化学释放出化合物的活性形式以及化合物的光化学异构化反应，特别是从顺式到反式形式的化合物。这些反应可以单独或组合使用，将化合物的非活性或相对不活性形式转化为更活跃的形式，从而使化合物能够被选择性地靶向，例如在肿瘤部位激活它们。
• SUBSTITUTED STILBENES AND THEIR REACTIONS
  申请人：Hadfield John Anthony

  公开号：US20130023663A1

  公开（公告）日：2013-01-24

  The present invention relates to stilbene and quinine compounds related to combretastatin A-4 and their use as anticancer compounds and prodrugs. The compounds include those with an alkyl group on the double bond of cis- or trans-stilbenes, compounds with one or more (and preferably 2 or 3) alkyl group substituents on the stilbene A ring, compounds with an alkoxy group other than methoxy at position 3, 4, and/or 5 of the stilbene A ring, compounds (or prodrugs) in which BBOC amino acid esters are formed with the phenolic hydroxyl at the 3 -position of the B ring and compounds (or prodrugs) based on a benzoquinone B ring. The present invention further relates to the photochemical reactions of stilbene compounds, either the above compounds disclosed for the first time herein or compounds based on prior stilbenes. These reactions include the photochemical release of an active form of the compound from a prodrug conjugate and the photochemical isomerization of the compounds, especially from a trans to cis form of compounds. The reactions can be used alone or in combination to convert inactive or comparatively less active forms of the compounds to more active forms, thereby allowing the compounds to be selectively targeted, e.g., activating them at the site of a tumour.

  本发明涉及与Combretastatin A-4相关的Stilbene和Chinoline化合物及其作为抗癌化合物和前药的使用。这些化合物包括具有顺式或反式Stilbene双键上的烷基基团的化合物，具有一个或多个（最好是2或3个）烷基基团取代Stilbene A环的化合物，具有3、4和/或5位于Stilbene A环上的甲氧基以外的烷氧基的化合物，以及基于苯醌B环的化合物（或前药）和在B环的3位的酚羟基处形成BBOC氨基酸酯的化合物（或前药）。本发明还涉及Stilbene化合物的光化学反应，无论是首次在此处披露的上述化合物还是基于先前的Stilbenes的化合物。这些反应包括从前药共轭物中光化学释放化合物的活性形式和化合物的光化学异构化反应，特别是从顺式到反式的化合物。这些反应可以单独或组合使用，将化合物的非活性或相对不活性形式转化为更活性的形式，从而允许选择性地靶向这些化合物，例如在肿瘤部位激活它们。
• SUBSTITUTED STILBENES, THEIR REACTIONS AND ANTICANCER ACTIVITY
  申请人：Cancer Research Ventures Limited

  公开号：EP1351912A2

  公开（公告）日：2003-10-15
• US7220784B2
  申请人：——

  公开号：US7220784B2

  公开（公告）日：2007-05-22
• US8853270B2
  申请人：——

  公开号：US8853270B2

  公开（公告）日：2014-10-07