9-hydroxy-2,6-dimethyl-4H-pyrrolo<3,2,1-ij>quinolin-4-one | 131195-81-8

• 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: 9-hydroxy-2,6-dimethyl-4H-pyrrolo<3,2,1-ij>quinolin-4-one
• 英文别名: 2,6-dimethyl-9-hydroxypyrrolo<3,2,1-ij>quinolin-4-one；5-Hydroxy-2,9-dimethyl-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12),9-pentaen-11-one
• CAS: 131195-81-8
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: HOJZNVNBGMWIHH-UHFFFAOYSA-N

物化性质

• 熔点：
  282 °C(Solv: methanol (67-56-1))
• 沸点：
  306.8±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-hydroxy-2,6-dimethyl-4H-pyrrolo<3,2,1-ij>quinolin-4-one 在 potassium carbonate 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 24.75h， 生成 9-{4'-[2"-(dimethylamino)ethylamino]butoxy}-2,6-dimethylpyrrolo[3,2,1-ij]quinolin-4-one
  参考文献：
  名称：

  Pyrroloquinolinone-based dual topoisomerase I/II inhibitor

  摘要：

  A new series of pyrroloquinolinones bearing different alkylamino side chains were synthesized and evaluated as cytotoxic compounds against three different human tumor cell lines (HeLa, HL-60 and A431). Some compounds showed interesting antiproliferative activity, in particular against A431 cells. The compounds were tested for their ability to counteract topoisomerase II relaxation activity and the most interesting one (3c) was tested also against topoisomerase I, resulting a dual inhibitor. The molecular interactions between 3c and the intracellular targets were finally investigated through molecular modeling simulations. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.064
• 作为产物：
  描述：

  间苯二胺 在 氢氧化钾 、 硫酸 、 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 、 N,N-二乙基苯胺 、 sodium nitrite 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 59.67h， 生成 9-hydroxy-2,6-dimethyl-4H-pyrrolo<3,2,1-ij>quinolin-4-one
  参考文献：
  名称：

  New synthesis of pyrrolo [3,2,1-ij] quinolin-4-one derivatives

  摘要：

  A new convenient synthesis of pyrrolo[3,2,1-ij]quinolin-4-one derivatives is described. In this method, methyl-7-hydroxquinoline-2-ones are the starting materials onto which the third pyrrolo ring is condensed directly, yielding dehydrogenated methyl-9-hydroxypyrrolo[3,2,1-ij]quinolin-4-ones.

  DOI：

  10.1021/jo00003a016

文献信息

• CHILIN, A.;RODIGHIERO, P.;PASTORINI, G.;GUIOTTO, A., J. ORG. CHEM., 56,(1991) N, C. 980-983
  作者：CHILIN, A.、RODIGHIERO, P.、PASTORINI, G.、GUIOTTO, A.

  DOI：——

  日期：——
• Rodighiero, Paolo; Chilin, Adriana; Bandoli, Giuliano, Gazzetta Chimica Italiana, 1994, vol. 124, # 4, p. 167 - 172
  作者：Rodighiero, Paolo、Chilin, Adriana、Bandoli, Giuliano、Manzini, Paolo、Castellin, Andrea、Guiotto, Adriano

  DOI：——

  日期：——