5,7-Diiodoisatin | 34058-26-9

• 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: 5,7-Diiodoisatin
• 英文别名: 5,7-diiodo-indoline-2,3-dione；5,7-Dijod-indolin-2,3-dion；5,7-Di-iodisatin；5,7-diiodo-1H-indole-2,3-dione
• CAS: 34058-26-9
• 化学式: C₈H₃I₂NO₂
• 分子量: 398.926
• InChiKey: HXBUSFFADZWMJT-UHFFFAOYSA-N

物化性质

• 熔点：
  259-260 °C(Solv: water (7732-18-5))
• 密度：
  2.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,7-Diiodoisatin 在 硫酸 、 碘 、 potassium iodide 作用下， 生成 3,3-bis-(4-hydroxy-3,5-diiodo-phenyl)-5,7-diiodo-indolin-2-one
  参考文献：
  名称：

  THE PREPARATION OF CERTAIN IODINATED DERIVATIVES OF PHENOLISATIN

  摘要：

  DOI：

  10.1021/ja01348a042
• 作为产物：
  描述：

  5′-iodospiro[[1,3]dioxolane-2,3′-indolin]-2′-one 在 盐酸 、 一氯化碘 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.67h， 生成 5,7-Diiodoisatin
  参考文献：
  名称：

  In vitro cytotoxicity evaluation of some substituted isatin derivatives

  摘要：

  A range of substituted 1H-indole-2,3-diones (isatins) were synthesized using standard procedures and their cytotoxicity evaluated against the human monocyte-like histiocytic lymphoma (U937) cell line in vitro. SAR studies identified C-5, C-6, and C-7 substitution greatly enhanced activity with some di- and tri-halogenated isatins giving IC50 values < 10 mu M. Of the 23 compounds tested, four were selected for further screening against a panel of five human cancer cell lines. These compounds, in general, showed greater selectivity toward leukemia and lymphoma cells over breast, prostate, and colorectal carcinoma cell lines. The most active compound, 5,6,7-tribromoisatin (2p), was found to be antiproliferative at low micromolar concentrations and also activated the effector caspases 3 and 7 in a dose-dependent manner. These results indicate that di- and tri-substituted isatins may be useful leads for anticancer drug development in the future. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.035

文献信息

• Kalb; Berrer, Chemische Berichte, 1924, vol. 57, p. 2116
  作者：Kalb、Berrer

  DOI：——

  日期：——
• THE PREPARATION OF 5,7-DI-IODOISATIN
  作者：Ward C. Sumpter、Lawrence Amundsen

  DOI：10.1021/ja01344a027

  日期：1932.5
• Sumpter; Amundsen, Journal of the American Chemical Society, 1932, vol. 54, p. 1719
  作者：Sumpter、Amundsen

  DOI：——

  日期：——
• In vitro cytotoxicity evaluation of some substituted isatin derivatives
  作者：Kara L. Vine、Julie M. Locke、Marie Ranson、Stephen G. Pyne、John B. Bremner

  DOI：10.1016/j.bmc.2006.10.035

  日期：2007.1

  A range of substituted 1H-indole-2,3-diones (isatins) were synthesized using standard procedures and their cytotoxicity evaluated against the human monocyte-like histiocytic lymphoma (U937) cell line in vitro. SAR studies identified C-5, C-6, and C-7 substitution greatly enhanced activity with some di- and tri-halogenated isatins giving IC50 values < 10 mu M. Of the 23 compounds tested, four were selected for further screening against a panel of five human cancer cell lines. These compounds, in general, showed greater selectivity toward leukemia and lymphoma cells over breast, prostate, and colorectal carcinoma cell lines. The most active compound, 5,6,7-tribromoisatin (2p), was found to be antiproliferative at low micromolar concentrations and also activated the effector caspases 3 and 7 in a dose-dependent manner. These results indicate that di- and tri-substituted isatins may be useful leads for anticancer drug development in the future. (c) 2006 Elsevier Ltd. All rights reserved.
• THE PREPARATION OF CERTAIN IODINATED DERIVATIVES OF PHENOLISATIN
  作者：Ward C. Sumpter

  DOI：10.1021/ja01348a042

  日期：1932.9