(Z)-2-(4`-methoxy-3`,5`-dinitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethene | 1017293-90-1

• 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-(4`-methoxy-3`,5`-dinitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: 2-methoxy-1,3-dinitro-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene
• CAS: 1017293-90-1
• 化学式: C₁₈H₁₈N₂O₈
• 分子量: 390.35
• InChiKey: MOWYNSJVNYPGKM-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 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：
  129
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-methoxy-3,5-dinitrobenzaldehyde 、 三苯基-(3,4,5-三甲氧基-苄基)-溴化膦 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以45%的产率得到(Z)-2-(4`-methoxy-3`,5`-dinitrophenyl)-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

• US7384925B2
  申请人：——

  公开号：US7384925B2

  公开（公告）日：2008-06-10
• USRE45720E1
  申请人：——

  公开号：USRE45720E1

  公开（公告）日：2015-10-06
• USRE45907E1
  申请人：——

  公开号：USRE45907E1

  公开（公告）日：2016-03-01
• Combretastatin Dinitrogen-Substituted Stilbene Analogues as Tubulin-Binding and Vascular-Disrupting Agents
  作者：Rogelio Siles、J. Freeland Ackley、Mallinath B. Hadimani、John J. Hall、Benon E. Mugabe、Rajsekhar Guddneppanavar、Keith A. Monk、Jean-Charles Chapuis、George R. Pettit、David J. Chaplin、Klaus Edvardsen、Mary Lynn Trawick、Charles M. Garner、Kevin G. Pinney

  DOI：10.1021/np070377j

  日期：2008.3.1

  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.