3,6-diamino-N2,N5-di(2,5,8,11-tetraoxatridecan-13-yl)pyrazine-2,5-dicarboxamide | 1374414-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,6-diamino-N2,N5-di(2,5,8,11-tetraoxatridecan-13-yl)pyrazine-2,5-dicarboxamide
• 英文别名: 3,6-diamino-2-N,5-N-bis[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl]pyrazine-2,5-dicarboxamide
• CAS: 1374414-36-4
• 化学式: C₂₄H₄₄N₆O₁₀
• 分子量: 576.648
• InChiKey: GOMIGACTBAGVGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  40
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  210
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3,6-diamino-N2,N5-di(2,5,8,11-tetraoxatridecan-13-yl)pyrazine-2,5-dicarboxamide trifluoroacetic acid salt 在 碳酸氢钠 作用下， 生成 3,6-diamino-N2,N5-di(2,5,8,11-tetraoxatridecan-13-yl)pyrazine-2,5-dicarboxamide
  参考文献：
  名称：

  Exogenous fluorescent tracer agents based on pegylated pyrazine dyes for real-time point-of-care measurement of glomerular filtration rate

  摘要：

  Novel pyrazine carboxamides bearing hydrophilic poly(ethylene glycol) (PEG) moieties were designed, synthesized, and evaluated for use as fluorescent glomerular filtration rate (GFR) tracer agents. Among these, compounds 4d and 5c that contain about 48 ethylene oxide units in the PEG chain exhibited the most favorable physicochemical and renal clearance properties. In vitro studies show that these two compounds have low plasma protein binding, a necessary condition for renal excretion. In vivo animal model results show that 4d and 5c have a higher urine recovery of the injected dose than iothalamate (a commonly considered gold standard GFR agent). Pharmacokinetic studies show that these two compounds exhibit a plasma clearance equivalent to iothalamate, but with a faster (i.e. lower) terminal half-life than iothalamate (possibly from restricted distribution into the extracellular space due to large molecular size and hydrodynamic volume). Furthermore, the plasma clearance of 4d and 5c remained unchanged upon blockage of the tubular secretion pathway with probenecid, a necessary condition for establishment of clearance via glomerular filtration exclusively. Finally, noninvasive real-time monitoring of this class of compounds was demonstrated by pharmacokinetic clearance of 5c by optical measurements in rat model, which correlates strongly with plasma concentration of the tracer. Hence, 4d and 5c are promising candidates for translation to the clinic as exogenous fluorescent tracer agents in real-time point-of-care monitoring of GFR. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.015