2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]cyclohexa-2,5-diene-1,4-dione | 438534-77-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 438534-77-1
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: ANIWDLFWTBEKFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]cyclohexa-2,5-diene-1,4-dione 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054
• 作为产物：
  描述：

  1,1-dibromo-2-(2,4,5-trimethoxyphenyl)ethene 在 silver(II) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 palladium diacetate 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 为溶剂， -78.0~145.0 ℃ 、344.75 kPa 条件下， 反应 19.83h， 生成 2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethyl]cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054

文献信息

• 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。
• 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
• Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer
  作者：Shankar Thangaraj、Wen-Shing Tsao、Yi-Wei Luo、Yean-Jang Lee、Chia-Fu Chang、Chun-Cheng Lin、Biing-Jiun Uang、Chia-Chun Yu、Jih-Hwa Guh、Che-Ming Teng

  DOI：10.1016/j.tet.2011.06.054

  日期：2011.8

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.