5-氯-2-(2-羟基乙基)异吲哚-1,3-二酮 | 78139-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 5-氯-2-(2-羟基乙基)异吲哚-1,3-二酮
• 英文名称: 5-Chloro-2-(2-hydroxy-ethyl)-isoindole-1,3-dione
• 英文别名: 5-Chloro-2-(2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione；5-chloro-2-(2-hydroxyethyl)isoindole-1,3-dione
• CAS: 78139-78-3
• 化学式: C₁₀H₈ClNO₃
• 分子量: 225.631
• InChiKey: WGFBIMKHOTXNPG-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  403.2±30.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dihydroartemisinin 、 5-氯-2-(2-羟基乙基)异吲哚-1,3-二酮 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 以32%的产率得到5-chloro-2-[2-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  Antimalarial activity of new ethers and thioethers of dihydroartemisinin

  摘要：

  Various ethers and thioethers of dihydroartemisinin were prepared by treating dihydroartemisinin with hydroxy alkyl, substituted phenol, hydroxy aralkyl, hydroxy alkynyl and hydroxy heteroalkyl or thiols in the presence of BF(3)Et(2)O. The thioethers 64 and 65 were further oxidised to the respective sulfoxides. These derivatives were tested in the Plasmodium berghei K-173-infected mice and some active compounds were tested in chloroquine-resistant P yoelii nigeriensis (NS)-infected mice. Initially the compounds were administered subcutaneously and subsequently by the oral route. The antimalarial activity of the compounds 22, 23, 36, 66 and 79 were found to be comparable to that of arteether when tested in the K-173-infected mice. These compounds also showed activity in the P y nigeriensis (NS)-infected mice.

  DOI：

  10.1016/0223-5234(96)88287-0

文献信息

• Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
  申请人：Sugen. Inc.

  公开号：US20030100555A1

  公开（公告）日：2003-05-29

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及吡咯替代的2-吲哚酮化合物及其药学上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。
• US6797725B2
  申请人：——

  公开号：US6797725B2

  公开（公告）日：2004-09-28
• US7053114B2
  申请人：——

  公开号：US7053114B2

  公开（公告）日：2006-05-30
• [EN] PRODRUGS OF 3-(PYRROL-2-YLMETHYLIDENE)-2-INDOLINONE DERIVATIVES<br/>[FR] PROMEDICAMENTS A BASE DE DERIVES 3-(PYRROL-2-YLMETHYLIDENE)-2-INDOLINONE
  申请人：SUGEN INC

  公开号：WO2002081466A1

  公开（公告）日：2002-10-17

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.
• Antimalarial activity of new ethers and thioethers of dihydroartemisinin
  作者：B Venugopalan、PJ Karnik、CP Bapat、DK Chatterjee、N Iyer、D Lepcha

  DOI：10.1016/0223-5234(96)88287-0

  日期：1995.1

  Various ethers and thioethers of dihydroartemisinin were prepared by treating dihydroartemisinin with hydroxy alkyl, substituted phenol, hydroxy aralkyl, hydroxy alkynyl and hydroxy heteroalkyl or thiols in the presence of BF(3)Et(2)O. The thioethers 64 and 65 were further oxidised to the respective sulfoxides. These derivatives were tested in the Plasmodium berghei K-173-infected mice and some active compounds were tested in chloroquine-resistant P yoelii nigeriensis (NS)-infected mice. Initially the compounds were administered subcutaneously and subsequently by the oral route. The antimalarial activity of the compounds 22, 23, 36, 66 and 79 were found to be comparable to that of arteether when tested in the K-173-infected mice. These compounds also showed activity in the P y nigeriensis (NS)-infected mice.