1-Butyl-5-iodo-1H-indole-2,3-dione | 898542-39-7

• 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-Butyl-5-iodo-1H-indole-2,3-dione
• 英文别名: 1-Butyl-5-iodoindoline-2,3-dione；1-butyl-5-iodoindole-2,3-dione
• CAS: 898542-39-7
• 化学式: C₁₂H₁₂INO₂
• 分子量: 329.137
• InChiKey: DKYBERVCUALHHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Butyl-5-iodo-1H-indole-2,3-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 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 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 1-Butyl-2,3-dioxo-2,3-dihydro-1H-indole-5-carboxylic acid amide
  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：

  5-碘吲哚醌 、 1-碘丁烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 1-Butyl-5-iodo-1H-indole-2,3-dione
  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

• Stereoselective Synthesis of Dispirooxindoles Incorporating Pyrrolo[2,1-a]isoquinoline via [3+2] Cycloaddition of Azomethine Ylides with a Thiazolo[3,2-a]indole Dipolarophile
  作者：Ani Deepthi、Noble V. Thomas、C. B. Meenakshy、Sruthi S. Leena

  DOI：10.1055/a-1777-2423

  日期：2022.6

  AbstractHighly regio- and stereoselective synthesis of dispiropyrrolo[2,1-a]isoquinoline-oxindoles have been developed by the one-pot three component reaction of isatins, 1,2,3,4-tetrahydroisoquinoline (THIQ), and a thiazolo[3,2-a]indole derivative. The reaction proceeds regioselectively through an exo-Re face approach of the in situ generated tetrahydroisoquinolium ylides towards the dipolarophile

  摘要通过靛红、1,2,3,4-四氢异喹啉 (THIQ) 和噻唑啉 [3 ,2-a]吲哚衍生物。该反应通过原位产生的四氢异喹啉叶立德向亲偶极体的外-Re面方法区域选择性地进行，以优异的产率和立体选择性产生相应的[3+2]环加合物。
• 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.