(S)-1-(4-iodobenzyl)-5-[1-(2-phenoxymethylpyrrolidinyl)sulfonyl]isatin

• 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-iodobenzyl)-5-[1-(2-phenoxymethylpyrrolidinyl)sulfonyl]isatin
• 英文别名: (S)-1-(4-iodobenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)isatin；1-[(4-iodophenyl)methyl]-5-[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonylindole-2,3-dione
• 化学式: C₂₆H₂₃IN₂O₅S
• 分子量: 602.45
• InChiKey: OOMWRPAWHLYIEI-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-iodobenzyl)-5-[1-(2-phenoxymethylpyrrolidinyl)sulfonyl]isatin 生成 N-[1-(2-Fluoroethyl)-1H-[1,2,3]-triazol-4-yl]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
• 作为产物：
  描述：

  L-脯氨醇 在 吡啶 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 (S)-1-(4-iodobenzyl)-5-[1-(2-phenoxymethylpyrrolidinyl)sulfonyl]isatin
  参考文献：
  名称：

  5-Pyrrolidinylsulfonyl Isatins as a Potential Tool for the Molecular Imaging of Caspases in Apoptosis

  摘要：

  Caspases are the unique enzymes responsible for the execution of the cell death program and may represent an exclusive target for the specific molecular imaging of apoptosis in vivo. 5-Pyrrolidinylsulfonyl isatins represent potent nonpeptidyl caspase inhibitors that may be suitable for the development of caspase binding radioligands ( CBRs). ( S)-5-[ 1-(2-Methoxymethylpyrrolidinyl) sulfonyl] isatin ( 7) served as a lead compound for modification of its N-1-position. Corresponding pairs of N-1-substituted 2-methoxymethyl- and 2-phenoxymethylpyrrolidinyl derivatives were examined in vitro by biochemical caspase inhibition assays. All target compounds possess high in vitro caspase inhibtion potencies in the nanomolar to subnanomolar range for caspase-3 ( K-i = 0.2- 56.1 nM). As shown for compound ( S)-1-( 4-(2-fluoroethoxy) benzyl)-5-[ 1( 2-methoxymethylpyrrolidinyl) sulfonyl] isatin ( 35), the class of N-1-substituted 5-pyrrolidinylsulfonyl isatins competitively inhibits caspase-3. All caspase inhibitors show selectivity for the effector caspases-3 and -7 in vitro. The 2-methoxymethylpyrrolidinyl versions of the isatins appear to possess superior caspase inhibition potencies in cellular apoptosis inhibition assays compared with the 2-phenoxymethylpyrrolidinyl inhibitors.

  DOI：

  10.1021/jm051217c

文献信息

• 5-PYRROLIDINYLSULFONYL-ISATIN DERIVATIVES
  申请人：Universitatsklinikum Munster

  公开号：US20130149239A1

  公开（公告）日：2013-06-13

  The present invention relates to novel 5 -pyrrolidinylsulfonyl isatin derivatives, non-peptidyl Caspase binding Radioligands (CbRs) and CbR-transporter conjugates derived from said isatin derivatives, diagnostic compositions comprising said compounds of the invention and their use for non-invasive diagnostic imaging.
• 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.
• 5-Pyrrolidinylsulfonyl Isatins as a Potential Tool for the Molecular Imaging of Caspases in Apoptosis
  作者：Klaus Kopka、Andreas Faust、Petra Keul、Stefan Wagner、Hans-Jörg Breyholz、Carsten Höltke、Otmar Schober、Michael Schäfers、Bodo Levkau

  DOI：10.1021/jm051217c

  日期：2006.11.1

  Caspases are the unique enzymes responsible for the execution of the cell death program and may represent an exclusive target for the specific molecular imaging of apoptosis in vivo. 5-Pyrrolidinylsulfonyl isatins represent potent nonpeptidyl caspase inhibitors that may be suitable for the development of caspase binding radioligands ( CBRs). ( S)-5-[ 1-(2-Methoxymethylpyrrolidinyl) sulfonyl] isatin ( 7) served as a lead compound for modification of its N-1-position. Corresponding pairs of N-1-substituted 2-methoxymethyl- and 2-phenoxymethylpyrrolidinyl derivatives were examined in vitro by biochemical caspase inhibition assays. All target compounds possess high in vitro caspase inhibtion potencies in the nanomolar to subnanomolar range for caspase-3 ( K-i = 0.2- 56.1 nM). As shown for compound ( S)-1-( 4-(2-fluoroethoxy) benzyl)-5-[ 1( 2-methoxymethylpyrrolidinyl) sulfonyl] isatin ( 35), the class of N-1-substituted 5-pyrrolidinylsulfonyl isatins competitively inhibits caspase-3. All caspase inhibitors show selectivity for the effector caspases-3 and -7 in vitro. The 2-methoxymethylpyrrolidinyl versions of the isatins appear to possess superior caspase inhibition potencies in cellular apoptosis inhibition assays compared with the 2-phenoxymethylpyrrolidinyl inhibitors.
• 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。