6-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-6'-hydroxy-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide | 1233979-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-6'-hydroxy-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide
• 英文别名: 2-[2-[2-(3-chloro-4-fluoroanilino)-2-oxoethoxy]-3-methoxy-6-(methylcarbamoyl)phenyl]-3-hydroxy-4-methoxy-N-methylbenzamide
• CAS: 1233979-32-2
• 化学式: C₂₆H₂₅ClFN₃O₇
• 分子量: 545.952
• InChiKey: AYNABSWBMNNAIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-6'-hydroxy-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 、 N-(2-氯乙基)吗啉盐酸盐 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以72%的产率得到6-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-5,5'-dimethoxy-N,N'-dimethyl-6'-(2-morpholin-4-ylethoxy)biphenyl-2,2'-dicarboxamide
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents

  摘要：

  Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC(50) = 52.5 mu M) and ECV304 (IC(50) = 2.67 mu M) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.001
• 作为产物：
  描述：

  6,6'-dihydroxy-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 以76%的产率得到6-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-6'-hydroxy-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents

  摘要：

  Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC(50) = 52.5 mu M) and ECV304 (IC(50) = 2.67 mu M) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.001

文献信息

• Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents
  作者：Jie Zhang、Yanmin Zhang、Yuanyuan Shan、Na Li、Wei Ma、Langchong He

  DOI：10.1016/j.ejmech.2010.03.001

  日期：2010.7

  Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC(50) = 52.5 mu M) and ECV304 (IC(50) = 2.67 mu M) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine. (C) 2010 Elsevier Masson SAS. All rights reserved.