1-(Benzenesulfonyl)-2-(morpholine-4-carbonyl)indole-4,7-dione | 845619-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(Benzenesulfonyl)-2-(morpholine-4-carbonyl)indole-4,7-dione
• CAS: 845619-30-9
• 化学式: C₁₉H₁₆N₂O₆S
• 分子量: 400.412
• InChiKey: NRZSVYTTYZYHTG-UHFFFAOYSA-N

物化性质

• 熔点：
  215.2-215.7 °C
• 沸点：
  719.4±70.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(Benzenesulfonyl)-2-(morpholine-4-carbonyl)indole-4,7-dione 在 盐酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 以83%的产率得到2-(morpholine-4-carbonyl)-1H-indole-4,7-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 2-acyl-1H-indole-4,7-diones on human cancer cell lines

  摘要：

  Synthesis and cytotoxic activity of a series of 2-acyl-1H-indole-4,7-diones on human cancer cell lines are described. Due to close structural relationship to 2-acylindoles, potent inhibitors of tubulin polymerization, the mode of action of these novel compounds has been investigated. Cytotoxicity, the influence on tubulin polymerization, and cell cycle dependent cytotoxicity on colon carcinoma cells by investigation of RKO exo p27 versus RKO p27(kip1) cells are described. IC50 values of arrested versus proliferating cells differ only in a range of two to fourfold and therefore cellular targets, predominantly relevant for mitotic progression, are excluded. As shown by the significant difference in the IC90 values on different tumor cell lines, the investigated compounds seem to act selectively on mammary and renal cancer cells. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.10.007
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 palladium on activated charcoal 正丁基锂 、 ammonium cerium(IV) nitrate 、 氢气 、 硝酸 、 甲酸铵 、 sodium acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 13.0h， 生成 1-(Benzenesulfonyl)-2-(morpholine-4-carbonyl)indole-4,7-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 2-acyl-1H-indole-4,7-diones on human cancer cell lines

  摘要：

  Synthesis and cytotoxic activity of a series of 2-acyl-1H-indole-4,7-diones on human cancer cell lines are described. Due to close structural relationship to 2-acylindoles, potent inhibitors of tubulin polymerization, the mode of action of these novel compounds has been investigated. Cytotoxicity, the influence on tubulin polymerization, and cell cycle dependent cytotoxicity on colon carcinoma cells by investigation of RKO exo p27 versus RKO p27(kip1) cells are described. IC50 values of arrested versus proliferating cells differ only in a range of two to fourfold and therefore cellular targets, predominantly relevant for mitotic progression, are excluded. As shown by the significant difference in the IC90 values on different tumor cell lines, the investigated compounds seem to act selectively on mammary and renal cancer cells. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.10.007

文献信息

• Synthesis and cytotoxic activity of 2-acyl-1H-indole-4,7-diones on human cancer cell lines
  作者：Siavosh Mahboobi、Andreas Sellmer、Emerich Eichhorn、Thomas Beckers、Heinz-Herbert Fiebig、Gerhard Kelter

  DOI：10.1016/j.ejmech.2004.10.007

  日期：2005.1

  Synthesis and cytotoxic activity of a series of 2-acyl-1H-indole-4,7-diones on human cancer cell lines are described. Due to close structural relationship to 2-acylindoles, potent inhibitors of tubulin polymerization, the mode of action of these novel compounds has been investigated. Cytotoxicity, the influence on tubulin polymerization, and cell cycle dependent cytotoxicity on colon carcinoma cells by investigation of RKO exo p27 versus RKO p27(kip1) cells are described. IC50 values of arrested versus proliferating cells differ only in a range of two to fourfold and therefore cellular targets, predominantly relevant for mitotic progression, are excluded. As shown by the significant difference in the IC90 values on different tumor cell lines, the investigated compounds seem to act selectively on mammary and renal cancer cells. (C) 2004 Elsevier SAS. All rights reserved.