cis-5-{1-[2,5-bis(methoxymethyl)pyrrolidinyl]sulfonyl}isatin | 1445166-98-2

• 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: cis-5-{1-[2,5-bis(methoxymethyl)pyrrolidinyl]sulfonyl}isatin
• 英文别名: 5-[(2S,5R)-2,5-bis(methoxymethyl)pyrrolidin-1-yl]sulfonyl-1H-indole-2,3-dione
• CAS: 1445166-98-2
• 化学式: C₁₆H₂₀N₂O₆S
• 分子量: 368.411
• InChiKey: KZJOHAIKJPMFAP-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 cis-5-{1-[2,5-bis(methoxymethyl)pyrrolidinyl]sulfonyl}isatin 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以73%的产率得到cis-N-butyl-5-{1-[2,5-bis(methoxymethyl)pyrrolidinyl]sulfonyl}isatin
  参考文献：
  名称：

  Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7

  摘要：

  A series of new 4- or 5-substituted pyrrolidine derivatives of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin bearing additional n-butyl or 4-fluorobutyl groups at the isatin nitrogen were prepared and their inhibitory activities have been tested against caspases-3 and -7, which are known to participate in the execution of the programmed cell death, called apoptosis. Several analogues fluorinated at the 4-position of the pyrrolidine ring were also synthesized since such inhibitors might be developed as F-18-radiotracers for molecular imaging of activated caspases in vivo by PET. Enantiomerically pure diastereomeric 4-fluoropyrrolidinyl derivatives inhibited the enzymes in the nanomolar scale, i.e.100-1000 times more efficient than the corresponding 4-methoxy analogues. The 4,4-difluorinated compound showed the best result with IC50 = 362 nM and 178 nM for the aforementioned caspases. In contrast, the 4-methoxy and 4-trifluoromethyl analogues exhibited less inhibition potencies for the enzymes in the mu M scale, whereas all 4-OPEG(4) (PEG(4) = tetraethyleneglycol) and 5-methoxymethyl derivatives were inactive. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.011
• 作为产物：
  描述：

  cis-N-benzyl-2,5-bis(methoxymethyl)pyrrolidine 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 20.0 ℃ 、2.03 MPa 条件下， 反应 8.0h， 生成 cis-5-{1-[2,5-bis(methoxymethyl)pyrrolidinyl]sulfonyl}isatin
  参考文献：
  名称：

  Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7

  摘要：

  A series of new 4- or 5-substituted pyrrolidine derivatives of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin bearing additional n-butyl or 4-fluorobutyl groups at the isatin nitrogen were prepared and their inhibitory activities have been tested against caspases-3 and -7, which are known to participate in the execution of the programmed cell death, called apoptosis. Several analogues fluorinated at the 4-position of the pyrrolidine ring were also synthesized since such inhibitors might be developed as F-18-radiotracers for molecular imaging of activated caspases in vivo by PET. Enantiomerically pure diastereomeric 4-fluoropyrrolidinyl derivatives inhibited the enzymes in the nanomolar scale, i.e.100-1000 times more efficient than the corresponding 4-methoxy analogues. The 4,4-difluorinated compound showed the best result with IC50 = 362 nM and 178 nM for the aforementioned caspases. In contrast, the 4-methoxy and 4-trifluoromethyl analogues exhibited less inhibition potencies for the enzymes in the mu M scale, whereas all 4-OPEG(4) (PEG(4) = tetraethyleneglycol) and 5-methoxymethyl derivatives were inactive. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.011