(Z)-5-{2-[3-(2-propenyl)oxy-5-methoxyphenyl]-ethenyl}-2-methoxyphenylamine hydrochloride | 1072121-58-4

• 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: (Z)-5-{2-[3-(2-propenyl)oxy-5-methoxyphenyl]-ethenyl}-2-methoxyphenylamine hydrochloride
• 英文别名: (Z)-5-[2-(3-Allyloxy-5-methoxy-phenyl)-vinyl]-2-methoxy-phenylamine, hydrochloride；[2-methoxy-5-[(Z)-2-(3-methoxy-5-prop-2-enoxyphenyl)ethenyl]phenyl]azanium;chloride
• CAS: 1072121-58-4
• 化学式: C₁₉H₂₁NO₃*ClH
• 分子量: 347.842
• InChiKey: IIHJBWOYKJXCGN-YSMBQZINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-1-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-5-methoxy-3-(2-propenoxy)benzene 在 溶剂黄146 、 锌 、 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 以70%的产率得到(Z)-5-{2-[3-(2-propenyl)oxy-5-methoxyphenyl]-ethenyl}-2-methoxyphenylamine hydrochloride
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel stilbene-based antitumor agents

  摘要：

  A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obstacle for a pre-clinical development. We have obtained derivatives with good cytotoxic activity, in particular, the derivatives 5c and 6b could represent two novel leads for further investigation. Compound 8b, a morpholino-carbamate derivative, prodrug of 1a, has a very good solubility in water, and is active in suppressing growth of tumor cells at a concentration of 5000 nM, which is a concentration 100 times higher than the parent stilbene 1a. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.002

文献信息

• Design, synthesis and biological evaluation of novel stilbene-based antitumor agents
  作者：Daniele Simoni、Francesco Paolo Invidiata、Marco Eleopra、Paolo Marchetti、Riccardo Rondanin、Riccardo Baruchello、Giuseppina Grisolia、Ashutosh Tripathi、Glen E. Kellogg、David Durrant、Ray M. Lee

  DOI：10.1016/j.bmc.2008.12.002

  日期：2009.1

  A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obstacle for a pre-clinical development. We have obtained derivatives with good cytotoxic activity, in particular, the derivatives 5c and 6b could represent two novel leads for further investigation. Compound 8b, a morpholino-carbamate derivative, prodrug of 1a, has a very good solubility in water, and is active in suppressing growth of tumor cells at a concentration of 5000 nM, which is a concentration 100 times higher than the parent stilbene 1a. (C) 2008 Elsevier Ltd. All rights reserved.