(Z)-1-(1,1-dimethylethyl)dimethylsilanoxy-3-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-5-methoxybenzene | 1073143-67-5

• 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)-1-(1,1-dimethylethyl)dimethylsilanoxy-3-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-5-methoxybenzene
• CAS: 1073143-67-5
• 化学式: C₂₂H₂₉NO₅Si
• 分子量: 415.561
• InChiKey: YGGPOOBRWHQTNZ-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-(1,1-dimethylethyl)dimethylsilanoxy-3-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-5-methoxybenzene 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(Z)-3-methoxy-5-[2-(4-methoxy-3-nitrophenyl)-ethenyl]phenol
  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
• 作为产物：
  描述：

  (4-methoxy-3-nitrobenzyl)triphenylphosphonium bromide 、 3-(tert-butyldimethylsilyloxy)-5-methoxybenzaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以40%的产率得到(Z)-1-(1,1-dimethylethyl)dimethylsilanoxy-3-[2-(4-methoxy-3-nitrophenyl)-ethenyl]-5-methoxybenzene
  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