(S)-1-(4-fluorobenzyl)-5-(2-(2-propynyloxymethyl)-pyrrolidine-1-sulfonyl)isatin | 1092522-66-1

• 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)-1-(4-fluorobenzyl)-5-(2-(2-propynyloxymethyl)-pyrrolidine-1-sulfonyl)isatin
• 英文别名: (S)-1-(4-fluorobenzyl)-5-(2-(2-propynyloxymethyl)pyrrolidine-1-sulfonyl)isatin；1-[(4-fluorophenyl)methyl]-5-[(2S)-2-(prop-2-ynoxymethyl)pyrrolidin-1-yl]sulfonylindole-2,3-dione
• CAS: 1092522-66-1
• 化学式: C₂₃H₂₁FN₂O₅S
• 分子量: 456.495
• InChiKey: UPVFUEYFEIBIGD-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-azido-2-fluoroethane 、 (S)-1-(4-fluorobenzyl)-5-(2-(2-propynyloxymethyl)-pyrrolidine-1-sulfonyl)isatin 在 copper(II) sulfate 、 维生素 C 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以48%的产率得到(S)-1-(4-fluorobenzyl)-5-(2-(1-((2-fluoroethyl)-1H-[1,2,3]triazol-4-yl)methoxymethyl)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：

  2,3-二氧代-2,3-二氢-1H-吲哚-5-磺酰氯 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 生成 (S)-1-(4-fluorobenzyl)-5-(2-(2-propynyloxymethyl)-pyrrolidine-1-sulfonyl)isatin
  参考文献：
  名称：

  ISATIN DERIVATIVES FOR USE AS IN VIVO IMAGING AGENTS

  摘要：

  异吲哚啉-5-磺酰胺衍生物，包括这些衍生物的药物组合物，它们作为分子成像剂的用途，它们用于与凋亡失调相关的疾病或紊乱的诊断或治疗，合成这些衍生物的方法，用于测定caspase活性和凋亡的分子成像方法，以及评估试验物质对caspase活性的治疗效果的方法。

  公开号：

  US20110195024A1

文献信息

• US8961930B2
  申请人：——

  公开号：US8961930B2

  公开（公告）日：2015-02-24
• [EN] ISATIN DERIVATIVES FOR USE AS IN VIVO IMAGING AGENTS<br/>[FR] DÉRIVÉS D'ISATINE POUR UTILISATION EN TANT QU'AGENTS D'IMAGERIE IN VIVO
  申请人：IMP INNOVATIONS LTD

  公开号：WO2010026388A1

  公开（公告）日：2010-03-11

  The present invention provides isatin 5-sulfonamide derivatives, pharmaceutical compositions comprising said derivatives, their use as molecular imaging agents, their use for the diagnosis or treatment of diseases or disorders associated with dysregulation of apoptosis, methods for synthesizing said derivatives, methods for the molecular imaging of caspase activity and apoptosis, and methods of assessing the therapeutic effect of a test substance on caspase activity.
• 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.
• ISATIN DERIVATIVES FOR USE AS IN VIVO IMAGING AGENTS
  申请人：Aboabye Eric Ofori

  公开号：US20110195024A1

  公开（公告）日：2011-08-11

  Isatin 5-sulfonamide derivatives, pharmaceutical compositions comprising the derivatives, their use as molecular imaging agents, their use for the diagnosis or treatment of diseases or disorders associated with dysregulation of apoptosis, methods for synthesizing the derivatives, methods for the molecular imaging of caspase activity and apoptosis, and methods of assessing the therapeutic effect of a test substance on caspase activity are disclosed.

  异吲哚啉-5-磺酰胺衍生物，包括这些衍生物的药物组合物，它们作为分子成像剂的用途，它们用于与凋亡失调相关的疾病或紊乱的诊断或治疗，合成这些衍生物的方法，用于测定caspase活性和凋亡的分子成像方法，以及评估试验物质对caspase活性的治疗效果的方法。