2-(2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl 1H-imidazole-1-carboxylate | 1257408-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl 1H-imidazole-1-carboxylate
• CAS: 1257408-26-6
• 化学式: C₂₄H₃₈N₄O₁₁
• 分子量: 558.586
• InChiKey: GPIVCMSICFVUNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  39.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  152.85
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  IAC 、 2-(2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl 1H-imidazole-1-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以55%的产率得到(2S)-2-[2-[[3-[2-[2-[2-[2-[2-[2-[2-[2-[[3-[2-[[(1S)-1-carboxy-2-[[4-[2-(1,4,5,6-tetrahydropyrimidin-2-ylamino)ethoxy]benzoyl]amino]ethyl]sulfamoyl]ethylcarbamoyloxy]-2,2-dimethylpropyl]carbamoyloxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxycarbonylamino]-2,2-dimethylpropoxy]carbonylamino]ethylsulfonylamino]-3-[[4-[2-(1,4,5,6-tetrahydropyrimidin-2-ylamino)ethoxy]benzoyl]amino]propanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of bivalent, peptidomimetic antagonists of the αvβ3 integrins

  摘要：

  Targeting the integrin alpha(v)beta(3) by directly interfering with its function is considered to be an effective and non-cytotoxic strategy for the treatment of tumor. In this study, a series of bivalent analogs of peptidomimetic integrin antagonists IA 1 and IAC 2 were designed, synthesized, and evaluated for their ability to inhibit the integrin alpha(v)beta(3). All the bivalent ligands exhibited increased potency compared to that of their monomeric counterparts for the integrin alpha(v)beta(3) with low nanomolar range binding affinity. The best bivalent ligand 6 tested in the series has an IC50 = 0.09 nM evaluated by ELISA assay. We conclude that multivalency is providing a useful template for the development novel integrin alpha(v)beta(3) antagonists as potential therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.035
• 作为产物：
  描述：

  八乙二醇 、 N,N'-羰基二咪唑 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到2-(2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl 1H-imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of bivalent, peptidomimetic antagonists of the αvβ3 integrins

  摘要：

  Targeting the integrin alpha(v)beta(3) by directly interfering with its function is considered to be an effective and non-cytotoxic strategy for the treatment of tumor. In this study, a series of bivalent analogs of peptidomimetic integrin antagonists IA 1 and IAC 2 were designed, synthesized, and evaluated for their ability to inhibit the integrin alpha(v)beta(3). All the bivalent ligands exhibited increased potency compared to that of their monomeric counterparts for the integrin alpha(v)beta(3) with low nanomolar range binding affinity. The best bivalent ligand 6 tested in the series has an IC50 = 0.09 nM evaluated by ELISA assay. We conclude that multivalency is providing a useful template for the development novel integrin alpha(v)beta(3) antagonists as potential therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.035