6-chloro-7-(5-fluoropentyl)purine | 1549661-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-chloro-7-(5-fluoropentyl)purine
• CAS: 1549661-80-4
• 化学式: C₁₀H₁₂ClFN₄
• 分子量: 242.683
• InChiKey: FPTMMSLDGDWUGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  6-氯嘌呤 、 (5-fluoropentyl)tosylate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.0h， 以13%的产率得到6-chloro-7-(5-fluoropentyl)purine
  参考文献：
  名称：

  Development of Purine-Derived ¹⁸F-Labeled Pro-drug Tracers for Imaging of MRP1 Activity with PET

  摘要：

  Multidrug resistance-associated protein 1 (MRP1) is a drug efflux transporter that has been implicated in the pathology of several neurological diseases and is associated with development of multidrug resistance. To enable measurement of MRP1 function in the living brain, a series of 6-halopurines decorated with fluorinated side chains have been synthesized and evaluated as putative pro-drug tracers. The tracers were designed to undergo conjugation with glutathione within the brain and hence form the corresponding MRP1 substrate tracers in situ. 6-Bromo-7-(2-[F-18]fluoroethyl)purine showed good brain uptake and rapid metabolic conversion. Dynamic PET imaging demonstrated a marked difference in brain clearance rates between wild-type and mrp1 knockout mice, suggesting that the tracer can allow noninvasive assessment of MRP1 activity in vivo.

  DOI：

  10.1021/jm401764a