(Z)-2-(3',5`-diamino-4`-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene | 519060-23-2

• 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)-2-(3',5`-diamino-4`-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,3-diamine
• CAS: 519060-23-2
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: DSEBFHNYRZQEKH-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3',5`-diamino-4`-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 以26%的产率得到(Z)-2-(3`,5`-diamine-4`-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene dihydrochloride
  参考文献：
  名称：

  Combretastatin Dinitrogen-Substituted Stilbene Analogues as Tubulin-Binding and Vascular-Disrupting Agents

  摘要：

  Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents.

  DOI：

  10.1021/np070377j
• 作为产物：
  描述：

  (Z)-2-(4`-methoxy-3`,5`-dinitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethene 在 sodium dithionite 、 水 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以20%的产率得到(Z)-2-(3',5`-diamino-4`-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene
  参考文献：
  名称：

  Combretastatin Dinitrogen-Substituted Stilbene Analogues as Tubulin-Binding and Vascular-Disrupting Agents

  摘要：

  Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2',3'-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI(50) = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 mu M). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents.

  DOI：

  10.1021/np070377j

文献信息

• Functionalized stilbene derivatives as improved vascular targeting agents
  申请人：——

  公开号：US20030149003A1

  公开（公告）日：2003-08-07

  Novel stilbenoid compounds and their prodrug forms are disclosed, which serve as potent vascular targeting agents useful for the treatment of solid tumor cancers and other diseases associated with unwanted neovascularization. The novel stilbenoid compounds are tubulin-binding stilbenoid analogs structurally related to combretastatin A-1 and combretastatin A-4. The prodrug forms serve as potent vascular targeting agents (VTAs) useful for the treatment of solid tumor cancers and diseases associated with retinal neovascularization.

  本发明揭示了一种新型的苯乙烯类化合物及其前药形式，其作为强效的血管靶向剂，可用于治疗实体肿瘤癌和其他与不需要的新生血管化有关的疾病。这些新型的苯乙烯类化合物是微管结合的苯乙烯类类似物，其结构与康布雷他斯汀A-1和康布雷他斯汀A-4有关。前药形式作为强效的血管靶向剂（VTAs），可用于治疗实体肿瘤癌和与视网膜新生血管化有关的疾病。
• FUNCTIONALIZED STILBENE DERIVATIVES AS IMPROVED VASCULAR TARGETING AGENTS
  申请人：Oxigene, Inc.

  公开号：EP1438281A2

  公开（公告）日：2004-07-21
• EP1438281A4
  申请人：——

  公开号：EP1438281A4

  公开（公告）日：2006-04-26
• US6919324B2
  申请人：——

  公开号：US6919324B2

  公开（公告）日：2005-07-19
• US7384925B2
  申请人：——

  公开号：US7384925B2

  公开（公告）日：2008-06-10