4H-benzo[k]pyrrolo[3,2,1-de]phenanthridine-4,5(7H)-dione | 1393654-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4H-benzo[k]pyrrolo[3,2,1-de]phenanthridine-4,5(7H)-dione
• 英文别名: 13-Azapentacyclo[11.6.1.02,11.03,8.016,20]icosa-1(20),2(11),3,5,7,9,16,18-octaene-14,15-dione
• CAS: 1393654-34-6
• 化学式: C₁₉H₁₁NO₂
• 分子量: 285.302
• InChiKey: YEVNIFJXMVSVPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  4H-benzo[k]pyrrolo[3,2,1-de]phenanthridine-4,5(7H)-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以39%的产率得到2-bromo-4H-benzo[k]pyrrolo[3,2,1-de]phenanthridine-4,5(7H)-dione
  参考文献：
  名称：

  Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2-diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

  摘要：

  To further expand the structure cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 mu M) after 24 h. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.049
• 作为产物：
  描述：

  2-iodohydroxyiminoacetanilide 在 盐酸 、 硫酸 、 四丁基溴化铵 、 水 、 sodium acetate 、 palladium diacetate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 76.83h， 生成 4H-benzo[k]pyrrolo[3,2,1-de]phenanthridine-4,5(7H)-dione
  参考文献：
  名称：

  Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2-diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

  摘要：

  To further expand the structure cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 mu M) after 24 h. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.049

文献信息

• Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2-diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives
  作者：Lidia Matesic、Julie M. Locke、Kara L. Vine、Marie Ranson、John B. Bremner、Danielle Skropeta

  DOI：10.1016/j.tet.2012.06.049

  日期：2012.8

  To further expand the structure cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 mu M) after 24 h. (C) 2012 Elsevier Ltd. All rights reserved.