4-[[(2S)-pyrrolidin-2-yl]methoxy]pyrimidine | 1379444-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[[(2S)-pyrrolidin-2-yl]methoxy]pyrimidine
• CAS: 1379444-19-5
• 化学式: C₉H₁₃N₃O
• 分子量: 179.222
• InChiKey: QOIODRLWOOLFKQ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[[(2S)-pyrrolidin-2-yl]methoxy]pyrimidine 、 2,3-二氧代-2,3-二氢-1H-吲哚-5-磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 以51 mg的产率得到(S)-5-(2-(pyrimidin-4-yloxymethyl)pyrrolidine-1-sulfonyl)isatin
  参考文献：
  名称：

  Design, Synthesis, and Biological Characterization of a Caspase 3/7 Selective Isatin Labeled with 2-[¹⁸F]fluoroethylazide

  摘要：

  Imaging of programmed cell death (apoptosis) is important in the assessment of therapeutic response in oncology and for diagnosis in cardiac and neurodegenerative disorders. The executioner caspases 3 and 7 ultimately effect cellular death, thus providing selective molecular targets for in vivo quantification of apoptosis. To realize this potential, we aimed to develop F-18-labeled isatin sulfonamides with high metabolic,stability and moderate lipophilicity while retaining selectivity and affinity for caspase 3/7. A small library of isatins modified with fluorinated aromatic groups and heterocycles was synthesized. A lead compound incorporating 2'-fluoroethyl-1,2,3-triazole was identified with subnanomolar affinity for caspase 3. "Click labeling" provided the F-18-labeled tracer in 65 +/- 6% decay-corrected radiochemical yield from 2-[F-18]fluoroethylazide. The compound showed high stability in vivo with rapid uptake and elimination in healthy tissues and tumor. The novel F-18-labeled isatin is a candidate radiotracer for further preclinical evaluation for imaging of apoptosis.

  DOI：

  10.1021/jm801107u
• 作为产物：
  描述：

  (S)-tert-butyl 2-(pyrimidin-4-yloxymethyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-[[(2S)-pyrrolidin-2-yl]methoxy]pyrimidine
  参考文献：
  名称：

  Design, Synthesis, and Biological Characterization of a Caspase 3/7 Selective Isatin Labeled with 2-[¹⁸F]fluoroethylazide

  摘要：

  Imaging of programmed cell death (apoptosis) is important in the assessment of therapeutic response in oncology and for diagnosis in cardiac and neurodegenerative disorders. The executioner caspases 3 and 7 ultimately effect cellular death, thus providing selective molecular targets for in vivo quantification of apoptosis. To realize this potential, we aimed to develop F-18-labeled isatin sulfonamides with high metabolic,stability and moderate lipophilicity while retaining selectivity and affinity for caspase 3/7. A small library of isatins modified with fluorinated aromatic groups and heterocycles was synthesized. A lead compound incorporating 2'-fluoroethyl-1,2,3-triazole was identified with subnanomolar affinity for caspase 3. "Click labeling" provided the F-18-labeled tracer in 65 +/- 6% decay-corrected radiochemical yield from 2-[F-18]fluoroethylazide. The compound showed high stability in vivo with rapid uptake and elimination in healthy tissues and tumor. The novel F-18-labeled isatin is a candidate radiotracer for further preclinical evaluation for imaging of apoptosis.

  DOI：

  10.1021/jm801107u

文献信息

• Design, Synthesis, and Biological Characterization of a Caspase 3/7 Selective Isatin Labeled with 2-[¹⁸F]fluoroethylazide
  作者：Graham Smith、Matthias Glaser、Meg Perumal、Quang-De Nguyen、Bo Shan、Erik Årstad、Eric O. Aboagye

  DOI：10.1021/jm801107u

  日期：2008.12.25

  Imaging of programmed cell death (apoptosis) is important in the assessment of therapeutic response in oncology and for diagnosis in cardiac and neurodegenerative disorders. The executioner caspases 3 and 7 ultimately effect cellular death, thus providing selective molecular targets for in vivo quantification of apoptosis. To realize this potential, we aimed to develop F-18-labeled isatin sulfonamides with high metabolic,stability and moderate lipophilicity while retaining selectivity and affinity for caspase 3/7. A small library of isatins modified with fluorinated aromatic groups and heterocycles was synthesized. A lead compound incorporating 2'-fluoroethyl-1,2,3-triazole was identified with subnanomolar affinity for caspase 3. "Click labeling" provided the F-18-labeled tracer in 65 +/- 6% decay-corrected radiochemical yield from 2-[F-18]fluoroethylazide. The compound showed high stability in vivo with rapid uptake and elimination in healthy tissues and tumor. The novel F-18-labeled isatin is a candidate radiotracer for further preclinical evaluation for imaging of apoptosis.