(S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-1-[(S)-oxiran-2-ylmethyl]isatin | 1160524-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-1-[(S)-oxiran-2-ylmethyl]isatin
• 英文别名: 5-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl-1-[[(2S)-oxiran-2-yl]methyl]indole-2,3-dione
• CAS: 1160524-47-9
• 化学式: C₁₇H₂₀N₂O₆S
• 分子量: 380.422
• InChiKey: XRLQEVLRBDPXIT-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-1-[(S)-oxiran-2-ylmethyl]isatin 在 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 以51%的产率得到(S)-1-[(S)-3-fluoro-2-hydroxypropyl]-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin
  参考文献：
  名称：

  Fluorinated Isatin Derivatives. Part 2. New N-Substituted 5-Pyrrolidinylsulfonyl Isatins as Potential Tools for Molecular Imaging of Caspases in Apoptosis

  摘要：

  Caspases are responsible for the execution of the cell death program and are potentially suitable targets for the specific imaging of apoptosis in vivo. A series of N-1-substituted analogues of the small molecule nonpeptide caspase inhibitor (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (1), which may be useful for the development of caspase-targeted radioligands, were synthesized and their inhibition potencies were evaluated in vitro. Two of the most powerful techniques to introduce fluorine into organic compounds, viz, bromofluorination of olefins and fluorohydrin synthesis by ring-opening of epoxides, were used. Most of the target compounds are potent inhibitors of the two effector caspases-3 and -7. Furthermore, the F-18-radiolabeled model compound (S)-1-[4-(1-[F-18]fluoro-2-hydroxyethyl)benzyl]-5-[1-(2-methoxymethyl-pyrrolidinyl)sulfonyl]isatin ([F-18]37), a putative tracer for the noninvasive imaging of apoptosis by positron emission tomography (PET) was synthesized by nucleophilic epoxide ring-opening of its precursor 36. The radiochemistry utilized in the F-18-fluorination reverted to carrier-added [F-18]Et3N center dot 3HF, a new fluorine-18 source for radiolabeling.

  DOI：

  10.1021/jm8015014
• 作为产物：
  描述：

  (R)-(+)-间硝基苯磺酸缩水甘油酯 、 5-[[（（2S）-2-（甲氧甲基）-1-吡咯烷基]磺酰基]-1H-吲哚-2,3-二酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以56%的产率得到(S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-1-[(S)-oxiran-2-ylmethyl]isatin
  参考文献：
  名称：

  Fluorinated Isatin Derivatives. Part 2. New N-Substituted 5-Pyrrolidinylsulfonyl Isatins as Potential Tools for Molecular Imaging of Caspases in Apoptosis

  摘要：

  Caspases are responsible for the execution of the cell death program and are potentially suitable targets for the specific imaging of apoptosis in vivo. A series of N-1-substituted analogues of the small molecule nonpeptide caspase inhibitor (S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin (1), which may be useful for the development of caspase-targeted radioligands, were synthesized and their inhibition potencies were evaluated in vitro. Two of the most powerful techniques to introduce fluorine into organic compounds, viz, bromofluorination of olefins and fluorohydrin synthesis by ring-opening of epoxides, were used. Most of the target compounds are potent inhibitors of the two effector caspases-3 and -7. Furthermore, the F-18-radiolabeled model compound (S)-1-[4-(1-[F-18]fluoro-2-hydroxyethyl)benzyl]-5-[1-(2-methoxymethyl-pyrrolidinyl)sulfonyl]isatin ([F-18]37), a putative tracer for the noninvasive imaging of apoptosis by positron emission tomography (PET) was synthesized by nucleophilic epoxide ring-opening of its precursor 36. The radiochemistry utilized in the F-18-fluorination reverted to carrier-added [F-18]Et3N center dot 3HF, a new fluorine-18 source for radiolabeling.

  DOI：

  10.1021/jm8015014