(S)-1-(4-(2-(p-methylphenylsulfonyloxy)ethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin | 899818-44-1

• 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: (S)-1-(4-(2-(p-methylphenylsulfonyloxy)ethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin
• 英文别名: (S)-1-(4-(2-(4-methylphenylsulfonyloxy)ethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin；2-[4-[[5-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl-2,3-dioxoindol-1-yl]methyl]phenoxy]ethyl 4-methylbenzenesulfonate
• CAS: 899818-44-1
• 化学式: C₃₀H₃₂N₂O₉S₂
• 分子量: 628.724
• InChiKey: VXDALODUEXZZKU-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-(2-(p-methylphenylsulfonyloxy)ethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin 在 Kryptofix222[18F]钾盐 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 (S)-1-(4-(2-[18F]fluoroethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin
  参考文献：
  名称：

  WO2006/74799

  摘要：

  公开号：
• 作为产物：
  描述：

  1-(2-溴乙氧基)-4-甲基苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 28.0h， 生成 (S)-1-(4-(2-(p-methylphenylsulfonyloxy)ethoxy)benzyl)-5-[1-(2-methoxymethylpyrrolidinyl)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.
• [EN] 5-PYRROLIDINYLSULFONYL ISATIN DERIVATIVES<br/>[FR] DERIVES DE LA 5-PYRROLIDINYLSULFONYL ISATINE
  申请人：UNIVERSITAETSKLINIKUM MUENSTER

  公开号：WO2006074799A2

  公开（公告）日：2006-07-20

  [EN] 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.
  [FR] L'invention porte sur de nouveaux dérivés de la 5-pyrrolidinylsulfonyl isatine, sur des radioligands non peptidyles de fixation de la caspase (CbRs) et sur des conjugués transporteurs des CbRs dérivés desdits dérivés d'isatine. L'invention porte également sur des compositions diagnostiques comprenant lesdits composants de l'invention et sur leur utilisation dans l'imagerie de diagnostic non invasifs.
• 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.
• WO2006/74799
  申请人：——

  公开号：——

  公开（公告）日：——