3'-amino Ethoxy Combretastatin Glycinamide | 1015697-63-8

• 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: 3'-amino Ethoxy Combretastatin Glycinamide
• 英文别名: 2-amino-N-[2-ethoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]acetamide
• CAS: 1015697-63-8
• 化学式: C₂₁H₂₆N₂O₅
• 分子量: 386.448
• InChiKey: OPNFRJUMBPJXKC-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-1-(3,4,5-trimethoxy)phenyl-2-(3'-hydroxy-4'-ethoxy)phenylethylene Fmoc-glycinamide 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到3'-amino Ethoxy Combretastatin Glycinamide
  参考文献：
  名称：

  PREPARATION AND THE USE OF ETHOXY COMBRETASTATINS AND THEIR PRODRUGS

  摘要：

  该发明揭示了一种新型乙氧基康柏他静的全合成过程及其前药。康柏他静通过在其B芳香环的4'-位上进行乙氧基取代进行化学修饰，并通过修改其B芳香环的3'-位上的羟基转化为其磷酸盐的可溶性前药或磷酰胆碱的内盐。类似地，3'-氨基康柏他静经过4'-乙氧基化学修饰，进一步可以引入氨基酸的侧链到氨基上形成氨基酸酰胺的可溶性前药。所述化合物的结构如化学式(I)所示。乙氧基康柏他静具有强大的微管聚合抑制活性，可用于治疗抑制肿瘤或新生血管的情况。

  公开号：

  US20090170956A1

文献信息

• PREPARATION AND THE USE OF ETHOXY COMBRETASTATINS AND THEIR PRODRUGS
  申请人：Shen Weiping

  公开号：US20090170956A1

  公开（公告）日：2009-07-02

  The invention disclosed a total synthesis process of novel ethoxy combretastatins and their prodrugs. Combretastatins are chemically modified by ethoxy substituted on the 4′-position of their B aryl ring and are converted to be their soluble prodrugs of phosphate or their inner salt of phosphorylcholine by modifying the hydroxyl on the 3′-position of their B aryl ring. Similarly, 3′-amino combretastatin is 4′-ethoxy chemically modified and further side chain of amino acid can be introduced to the amino to form soluble prodrug of amino acidamide. The structure of the said compound is showed as formula (I). Ethoxy combretastatins possess potent tubulin polymerization inhibitory activity and can be used for the treatment of inhibiting tumor or neovascular.

  该发明揭示了一种新型乙氧基康柏他静的全合成过程及其前药。康柏他静通过在其B芳香环的4'-位上进行乙氧基取代进行化学修饰，并通过修改其B芳香环的3'-位上的羟基转化为其磷酸盐的可溶性前药或磷酰胆碱的内盐。类似地，3'-氨基康柏他静经过4'-乙氧基化学修饰，进一步可以引入氨基酸的侧链到氨基上形成氨基酸酰胺的可溶性前药。所述化合物的结构如化学式(I)所示。乙氧基康柏他静具有强大的微管聚合抑制活性，可用于治疗抑制肿瘤或新生血管的情况。
• ETHOXY DIPHENYL ETHANE DERIVATES, PREPARATION PROCESSES AND USES THEREOF
  申请人：Shanghai Ecust Biomedicine Co., Ltd

  公开号：EP2351730A1

  公开（公告）日：2011-08-03

  The invention discloses an ethoxydiphenylethane derivative and a synthetic method and uses thereof 4' position of phenylethane B aromatic ring is chemically modified by ethoxy and hydroxy at position 3' thereof is simultaneously modified to water soluble prodrug such as phosphate, and similarly, amino acid side chain is introduced to amino at position 3' to form amino acid amide water soluble prodrug having the structure shown as formula (I) the ethoxydiphenylethane derivative and the prodrug thereof include strong tubulin aggregation inhibiting ability and obvious target damage effect for tumor vessels, selectively cause dysfunction and structural damage of tumor vessels and induce apoptosis of vascular endothelial cells in order to play the role of killing tumor cells or inhibiting tumor metastasis in case that the tumor cells are free from the support of nutrition and oxygen.

  本发明公开了一种乙氧基二苯基乙烷衍生物及其合成方法和用途 苯基乙烷B芳环的4'位被乙氧基化学修饰，其3'位的羟基同时被修饰成磷酸酯等水溶性原药，同样，在3'位的氨基上引入氨基酸侧链，形成氨基酸酰胺类水溶性原药，其结构如式(I)所示 乙氧基二苯基乙烷衍生物及其原药具有较强的抑制小管蛋白聚集能力，对肿瘤血管具有明显的靶向损伤作用，可选择性地引起肿瘤血管功能障碍和结构破坏，诱导血管内皮细胞凋亡，从而在肿瘤细胞失去营养和氧气支持的情况下，起到杀灭肿瘤细胞或抑制肿瘤转移的作用。
• THE PREPARTION AND THE USE OF ETHOXY COMBRETASTATINS AND THEIR PRODRUGS
  申请人：Zhejiang Dade Pharmaceutical Group Co., Ltd.

  公开号：EP2065358B1

  公开（公告）日：2015-07-08