6H-pyrrolo[3,2,1-de]acridine-1,2-dione | 34756-36-0

• 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: 6H-pyrrolo[3,2,1-de]acridine-1,2-dione
• 英文别名: 6H-pyrrolo[1,2,3-de]acridine-1,2-dione；1-azatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6,9(16),10,12-hexaene-14,15-dione
• CAS: 34756-36-0
• 化学式: C₁₅H₉NO₂
• 分子量: 235.242
• InChiKey: IJXUZAFUIOPTBP-UHFFFAOYSA-N

物化性质

• 熔点：
  208-210 °C(Solv: ethanol (64-17-5))
• 沸点：
  424.4±48.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  6H-pyrrolo[3,2,1-de]acridine-1,2-dione 在 溴 、 溶剂黄146 作用下， 以41%的产率得到4-bromo-6H-pyrrolo[3,2,1-de]acridine-1,2-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：

  吖啶 在 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 29.0h， 生成 6H-pyrrolo[3,2,1-de]acridine-1,2-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 of acridan-fused quinoxalines
  作者：Mahlegha Shamsi、Mehdi M. Baradarani、Arash Afghan、John A. Joule

  DOI：10.3998/ark.5550190.0012.918

  日期：——

  The synthesis of acridan-fused quinoxalines, 10,14b-dihydro-1,6,14b-triazanaphth(a)- aceanthrylenes, 10,14b-dihydro-1,2,6,14b-tetraazanaphth(a)aceanthrylene, 10,14b-dihydro- 1,5,6,14b-tetraazanaphth(a)aceanthrylene and the acridan-fused pyrazine, 2,3-dicyano-8,12b- dihydro-1,4,12b-triazabenz(a)aceanthrylene, is described.

  吖啶稠合喹喔啉、10,14b-二氢-1,6,14b-triazanaphth(a)-aceanthrylenes, 10,14b-dihydro-1,2,6,14b-tetraazanaphth(a)aceanthrylene, 10,14b 的合成-二氢-1,5,6,14b-四氮杂萘(a)aceanthrylene和吖啶稠合吡嗪，2,3-二氰基-8,12b-二氢-1,4,12b-三氮杂苯并(a)aceanthrylene，被描述。
• Spiro[4<i>H</i> -pyran-3,3′-oxindoles] Derived from 9,10-dihydroacridine
  作者：Mousa Alipour、Mehdi M. Baradarani、John A. Joule

  DOI：10.1002/jhet.2809

  日期：2017.7

  Reaction 6H‐pyrrolo[3,2,1‐de]acridine‐1,2‐dione (7) with cyclic 1,3‐dicarbonyl compounds in the presence of malononitrile or ethyl cyanoacetate generates spiro[4H‐pyran‐3,3′‐oxindoles] 8.

  反应6 ħ吡咯并[3,2,1- DE ]吖啶-1,2-二酮（7）与丙二腈或氰基乙酸乙酯的存在环状1,3-二羰基化合物生成螺[4 ħ吡喃-3， 3'-oxindoles] 8。
• 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.