2-[(4-(chloromethyl)phenoxy)methyl]oxirane | 1160524-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(4-(chloromethyl)phenoxy)methyl]oxirane
• 英文别名: 2-[[4-(Chloromethyl)phenoxy]methyl]oxirane
• CAS: 1160524-46-8
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: GCAILKGCGQERGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(4-(chloromethyl)phenoxy)methyl]oxirane 、 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 9.0h， 以83%的产率得到(S)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]-1-[4-(oxiran-2-ylmethoxy)benzyl]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：

  4-allyloxybenzyl chloride 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 以74%的产率得到2-[(4-(chloromethyl)phenoxy)methyl]oxirane
  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

文献信息

• US4009128A
  申请人：——

  公开号：US4009128A

  公开（公告）日：1977-02-22
• US4047963A
  申请人：——

  公开号：US4047963A

  公开（公告）日：1977-09-13
• US5177151A
  申请人：——

  公开号：US5177151A

  公开（公告）日：1993-01-05
• US5225491A
  申请人：——

  公开号：US5225491A

  公开（公告）日：1993-07-06
• Fluorinated Isatin Derivatives. Part 2. New <i>N</i>-Substituted 5-Pyrrolidinylsulfonyl Isatins as Potential Tools for Molecular Imaging of Caspases in Apoptosis
  作者：Anil K. Podichetty、Stefan Wagner、Sandra Schröer、Andreas Faust、Michael Schäfers、Otmar Schober、Klaus Kopka、Günter Haufe

  DOI：10.1021/jm8015014

  日期：2009.6.11

  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.