1-Benzyl-2,3-dioxo-indoline-5-carboxylic acid | 898542-46-6

• 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: 1-Benzyl-2,3-dioxo-indoline-5-carboxylic acid
• 英文别名: 1-benzyl-2,3-dioxoindole-5-carboxylic acid
• CAS: 898542-46-6
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: SRXXVPDYEVSZPE-UHFFFAOYSA-N

物化性质

• 熔点：
  283-285 °C
• 沸点：
  546.4±60.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Benzyl-2,3-dioxo-indoline-5-carboxylic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1-Benzyl-2,3-dioxoindoline-5-carboxamide
  参考文献：
  名称：

  Isatin Compounds as Noncovalent SARS Coronavirus 3C-like Protease Inhibitors

  摘要：

  A series of isatin derivatives were synthesized and tested against SARS CoV 3C-like protease. Substitutions at the N-1 and C-5 positions were examined to elucidate the differences in substrate binding sites of the rhinovirus 3C protease and SARS CoV 3C-like protease. Compound 5f shows significant inhibition with an IC50 of 0.37 mu M. Further study showed that, unlike the irreversible covalent binding of isatin derivatives to human rhinovirus 3C protease, the compounds tested in this study are all noncovalent reversible inhibitors.

  DOI：

  10.1021/jm0602357
• 作为产物：
  描述：

  N-benzyl-5-iodoisatin 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 66.0h， 生成 1-Benzyl-2,3-dioxo-indoline-5-carboxylic acid
  参考文献：
  名称：

  Isatin Compounds as Noncovalent SARS Coronavirus 3C-like Protease Inhibitors

  摘要：

  A series of isatin derivatives were synthesized and tested against SARS CoV 3C-like protease. Substitutions at the N-1 and C-5 positions were examined to elucidate the differences in substrate binding sites of the rhinovirus 3C protease and SARS CoV 3C-like protease. Compound 5f shows significant inhibition with an IC50 of 0.37 mu M. Further study showed that, unlike the irreversible covalent binding of isatin derivatives to human rhinovirus 3C protease, the compounds tested in this study are all noncovalent reversible inhibitors.

  DOI：

  10.1021/jm0602357

文献信息

• Isatin Compounds as Noncovalent SARS Coronavirus 3C-like Protease Inhibitors
  作者：Lu Zhou、Ying Liu、Weilin Zhang、Ping Wei、Changkang Huang、Jianfeng Pei、Yaxia Yuan、Luhua Lai

  DOI：10.1021/jm0602357

  日期：2006.6.1

  A series of isatin derivatives were synthesized and tested against SARS CoV 3C-like protease. Substitutions at the N-1 and C-5 positions were examined to elucidate the differences in substrate binding sites of the rhinovirus 3C protease and SARS CoV 3C-like protease. Compound 5f shows significant inhibition with an IC50 of 0.37 mu M. Further study showed that, unlike the irreversible covalent binding of isatin derivatives to human rhinovirus 3C protease, the compounds tested in this study are all noncovalent reversible inhibitors.