4-[2-(2-{2-[2-(2-{2-[2-(2-prop-2-ynyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethyl]piperazin-1-ium trifluoroacetate | 1351556-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-[2-(2-{2-[2-(2-{2-[2-(2-prop-2-ynyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethyl]piperazin-1-ium trifluoroacetate
• 英文别名: 1-[2-[2-[2-[2-[2-[2-[2-(2-Prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]piperazine;2,2,2-trifluoroacetic acid
• CAS: 1351556-74-5
• 化学式: C₂HF₃O₂*C₂₃H₄₄N₂O₈
• 分子量: 590.635
• InChiKey: CYXBBSFYLJYFLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  40
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-bromo-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 、 4-[2-(2-{2-[2-(2-{2-[2-(2-prop-2-ynyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethyl]piperazin-1-ium trifluoroacetate 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-[4-(2-{2-[2-(2-{2-[2-(2-{2-[1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl-methoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethyl)piperazin-1-yl]-5-(4-phenoxyphenyl)pyrimidine-2,4,6-trione
  参考文献：
  名称：

  A New Generation of Radiofluorinated Pyrimidine-2,4,6-triones as MMP-Targeted Radiotracers for Positron Emission Tomography

  摘要：

  Radiolabeled C-5-disubstituted pyrimidine-2,4,6-triones have recently been suggested by our group as a class of potent matrix metalloproteinase (MMP) targeted radiotracers that can noninvasively visualize activated MMPs by means of positron emission tomography (PET). MMPs belong to the zinc- and calcium-dependent endopeptidases which are involved in the proteolytic degradation of components of the extracellular matrix (ECM) but also are capable of processing and releasing bioactive molecules such as growth factors, proteinase inhibitors, and cytokines. Locally increased levels of activated MMPs modulate and contribute to the progression of various diseases, such as cancer, atherosclerosis, stroke, arthritis, and others. Therefore, activated MMPs are suitable biological targets for the specific and noninvasive visualization of aforementioned pathologies in vivo. On the basis of our recent results, we here describe a series of new fluorinated pyrimidine-2,4,6-triones of the second generation with maintained MAP inhibition potencies (IC50 = 4-605 nM), which are fine-tuned toward more hydrophilic versions, and show the improved biodistribution behavior of one selected radiofluorinated pyrimidine-2,4,6-trione by means of small-animal PET.

  DOI：

  10.1021/jm201142w
• 作为产物：
  描述：

  丙炔-九聚乙二醇-对甲苯磺酸酯 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 4-[2-(2-{2-[2-(2-{2-[2-(2-prop-2-ynyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethoxy)ethyl]piperazin-1-ium trifluoroacetate
  参考文献：
  名称：

  A New Generation of Radiofluorinated Pyrimidine-2,4,6-triones as MMP-Targeted Radiotracers for Positron Emission Tomography

  摘要：

  Radiolabeled C-5-disubstituted pyrimidine-2,4,6-triones have recently been suggested by our group as a class of potent matrix metalloproteinase (MMP) targeted radiotracers that can noninvasively visualize activated MMPs by means of positron emission tomography (PET). MMPs belong to the zinc- and calcium-dependent endopeptidases which are involved in the proteolytic degradation of components of the extracellular matrix (ECM) but also are capable of processing and releasing bioactive molecules such as growth factors, proteinase inhibitors, and cytokines. Locally increased levels of activated MMPs modulate and contribute to the progression of various diseases, such as cancer, atherosclerosis, stroke, arthritis, and others. Therefore, activated MMPs are suitable biological targets for the specific and noninvasive visualization of aforementioned pathologies in vivo. On the basis of our recent results, we here describe a series of new fluorinated pyrimidine-2,4,6-triones of the second generation with maintained MAP inhibition potencies (IC50 = 4-605 nM), which are fine-tuned toward more hydrophilic versions, and show the improved biodistribution behavior of one selected radiofluorinated pyrimidine-2,4,6-trione by means of small-animal PET.

  DOI：

  10.1021/jm201142w

文献信息

• A New Generation of Radiofluorinated Pyrimidine-2,4,6-triones as MMP-Targeted Radiotracers for Positron Emission Tomography
  作者：Daniela Schrigten、Hans-Jörg Breyholz、Stefan Wagner、Sven Hermann、Otmar Schober、Michael Schäfers、Günter Haufe、Klaus Kopka

  DOI：10.1021/jm201142w

  日期：2012.1.12

  Radiolabeled C-5-disubstituted pyrimidine-2,4,6-triones have recently been suggested by our group as a class of potent matrix metalloproteinase (MMP) targeted radiotracers that can noninvasively visualize activated MMPs by means of positron emission tomography (PET). MMPs belong to the zinc- and calcium-dependent endopeptidases which are involved in the proteolytic degradation of components of the extracellular matrix (ECM) but also are capable of processing and releasing bioactive molecules such as growth factors, proteinase inhibitors, and cytokines. Locally increased levels of activated MMPs modulate and contribute to the progression of various diseases, such as cancer, atherosclerosis, stroke, arthritis, and others. Therefore, activated MMPs are suitable biological targets for the specific and noninvasive visualization of aforementioned pathologies in vivo. On the basis of our recent results, we here describe a series of new fluorinated pyrimidine-2,4,6-triones of the second generation with maintained MAP inhibition potencies (IC50 = 4-605 nM), which are fine-tuned toward more hydrophilic versions, and show the improved biodistribution behavior of one selected radiofluorinated pyrimidine-2,4,6-trione by means of small-animal PET.