2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)ethoxy)ethoxy)ethoxy)ethyl 1H-imidazole-1-carboxylate | 1000386-22-0

• 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-(1H-imidazole-1-carbonyloxy)ethoxy)ethoxy)ethoxy)ethyl 1H-imidazole-1-carboxylate
• 英文别名: 2-[2-[2-[2-(Imidazole-1-carbonyloxy)ethoxy]ethoxy]ethoxy]ethyl imidazole-1-carboxylate；2-[2-[2-[2-(imidazole-1-carbonyloxy)ethoxy]ethoxy]ethoxy]ethyl imidazole-1-carboxylate
• CAS: 1000386-22-0
• 化学式: C₁₆H₂₂N₄O₇
• 分子量: 382.373
• InChiKey: CULKDJGNRMXGJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  IAC 、 2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)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63%的产率得到(2S)-2-[2-[[3-[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]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：

  三缩四乙二醇 、 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85%的产率得到2-(2-(2-(2-(1H-imidazole-1-carbonyloxy)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

文献信息

• Labeled, Non-Peptidic, Multivalent Integrin Antagonist Compounds; Methods for Synthesis and Uses Thereof
  申请人：The Methodist Hospital Research Institute

  公开号：US20140044646A1

  公开（公告）日：2014-02-13

  Disclosed are multivalent, integrin-receptor antagonists that are useful in a variety of therapeutic, prophylactic, and/or diagnostic imaging modalities. In illustrative embodiments, such compounds have been prepared and utilized in the imaging, detection, localization, and/or quantitation of one or more samples of biological interest. Similarly, these compounds, as well as formulations comprising them, find utility in the prevention, treatment, and/or amelioration of one or more symptoms of a disease, abnormal condition, dysfunction, etc., including, for example proliferative diseases such as cancer in affected animals. In certain embodiments, fluorescently- or radio-labeled-non-peptidic, multivalent integrin α v β 3 compounds are provided. Compositions including such compounds have been shown to have utility in detecting, localizing, quantitating, and/or imaging integrin α v β 3 receptor-expressing cells, including, for example, cancer cells in vitro, in vivo, and/or in situ.
• US9833520B2
  申请人：——

  公开号：US9833520B2

  公开（公告）日：2017-12-05