(Z)1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)-prop-2-en-1-one | 1379535-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)-prop-2-en-1-one
• 英文别名: (Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyanilino)prop-2-en-1-one
• CAS: 1379535-63-3
• 化学式: C₁₉H₂₀BrNO₆
• 分子量: 438.275
• InChiKey: POHTUGYXBYJWNK-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基-2-溴苯甲醛 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成 (Z)1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)-prop-2-en-1-one
  参考文献：
  名称：

  (Z)-1-Aryl-3-arylamino-2-propen-1-ones, Highly Active Stimulators of Tubulin Polymerization: Synthesis, Structure–Activity Relationship (SAR), Tubulin Polymerization, and Cell Growth Inhibition Studies

  摘要：

  Tubulin, the major structural component of microtubules, is a target for the development of anticancer agents. A series of (Z)-1-aryl-3-arylamino-2-propen-1-one (10) were synthesized and evaluated for antiproliferative activity in cell-based assay. The most active compound (Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)prop-2-en-1-one (10ae) was tested in 20 tumor cell lines including multidrug resistant phenotype and was found to induce apoptosis in all these cell lines with similar GI(50) values. Flow cytometry studies showed that 10ae arrested the cells in G2/M phase of cell cycle. In addition to G2/M block, these compounds caused microtubule stabilization like paclitaxel and induced apoptosis via activation of the caspase family. The observations made in this investigation demonstrate that (Z)-1-Aryl-3-arylamino-2-propen-1-one (10) represents a new class of microtubule-stabilizing agents.

  DOI：

  10.1021/jm300176j

文献信息

• NOVEL 3,4,5-TRIMETHOXYSTYRYLARYLAMINOPROPENONES AS POTENTIAL ANTICANCER AGENTS
  申请人：Council of Scientific and Industrial Research

  公开号：US20150322009A1

  公开（公告）日：2015-11-12

  The present invention relate to compounds of general formula A. The invention also provides the synthesis of 3,4,5-trimethoxystyrylarylaminopropenones useful as potential antitumor agents against human cancer cell lines and a process for the preparation thereof. wherein: R=H, OMe, Cl, F, OH, Me X=aryl, heteroaryl

  本发明涉及一般式A的化合物。该发明还提供了3,4,5-三甲氧基苯乙烯基芳基氨基丙酮的合成方法，该方法可作为潜在的抗人类癌细胞系的抗肿瘤剂，并提供其制备过程。其中：R=H，OMe，Cl，F，OH，Me，X=芳基，杂环芳基。
• 3,4,5-TRIMETHOXYSTYRYLARYLAMINOPROPENONES for the treatment of cancer
  申请人：Council of Scientific and Industrial Research

  公开号：EP2942345A1

  公开（公告）日：2015-11-11

  The present invention relate to compounds of general formula A. The invention also provides the synthesis of 3,4,5-trimethoxystyrylarylaminopropenones useful as potential antitumor agents against human cancer cell lines and a process for the preparation thereof.

  本发明涉及通式 A 的化合物。本发明还提供了 3,4,5-三甲氧基苯乙烯基氨基丙烯酮的合成及其制备方法，该化合物可作为潜在的抗肿瘤剂用于人类癌细胞系。
• 3,4,5-TRIMETHOXYSTYRYLARYLAMINOPROPENONES FOR THE TREATMENT OF CANCER
  申请人：Council of Scientific and Industrial Research

  公开号：EP2942345B1

  公开（公告）日：2018-03-28
• US9487482B2
  申请人：——

  公开号：US9487482B2

  公开（公告）日：2016-11-08