1-(3-Dimethylamino-propylamino)-7-methoxy-4-nitro-10H-acridin-9-one | 99140-27-9

• 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: 1-(3-Dimethylamino-propylamino)-7-methoxy-4-nitro-10H-acridin-9-one
• 英文别名: 1-[3-(dimethylamino)propylamino]-7-methoxy-4-nitro-10H-acridin-9-one
• CAS: 99140-27-9
• 化学式: C₁₉H₂₂N₄O₄
• 分子量: 370.408
• InChiKey: BCZSGABZMYRXHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-Dimethylamino-propylamino)-7-methoxy-4-nitro-10H-acridin-9-one 在 镍 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 4-Amino-1-(3-dimethylamino-propylamino)-7-methoxy-10H-acridin-9-one
  参考文献：
  名称：

  Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias

  摘要：

  The synthesis of 8-hydroxy and 8-methoxy analogues of some substituted 5-aminoimidazoacridinones (4) is described. The synthesis was carried out by a three-step sequence from the corresponding 1-chloro-4-nitro-9(10H)-acridinone precursors (1). The annulation of the imidazolo ring onto the aminoacridinone chromophore was accomplished by heating the required aminoacridinone (3) with formic acid or, in the case of 1-methyl derivatives, with N,N-dimethylacetamide. Potent cytotoxic activity against L1210 leukemia, as well as antitumor activity against P388 leukemia in mice, was demonstrated for the 8-hydroxy analogues. The corresponding 8-methoxy derivatives were not cytotoxic. However, in some cases, they showed significant in vivo antileukemic activity.

  DOI：

  10.1021/jm00080a026
• 作为产物：
  描述：

  1-chloro-7-methoxy-4-nitro-9(10H)-acridinone 、 N,N-二甲基-1,3-二氨基丙烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以94%的产率得到1-(3-Dimethylamino-propylamino)-7-methoxy-4-nitro-10H-acridin-9-one
  参考文献：
  名称：

  Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias

  摘要：

  The synthesis of 8-hydroxy and 8-methoxy analogues of some substituted 5-aminoimidazoacridinones (4) is described. The synthesis was carried out by a three-step sequence from the corresponding 1-chloro-4-nitro-9(10H)-acridinone precursors (1). The annulation of the imidazolo ring onto the aminoacridinone chromophore was accomplished by heating the required aminoacridinone (3) with formic acid or, in the case of 1-methyl derivatives, with N,N-dimethylacetamide. Potent cytotoxic activity against L1210 leukemia, as well as antitumor activity against P388 leukemia in mice, was demonstrated for the 8-hydroxy analogues. The corresponding 8-methoxy derivatives were not cytotoxic. However, in some cases, they showed significant in vivo antileukemic activity.

  DOI：

  10.1021/jm00080a026

文献信息

• Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias
  作者：Wieslaw M. Cholody、Sante Martelli、Jerzy Konopa

  DOI：10.1021/jm00080a026

  日期：1992.1

  The synthesis of 8-hydroxy and 8-methoxy analogues of some substituted 5-aminoimidazoacridinones (4) is described. The synthesis was carried out by a three-step sequence from the corresponding 1-chloro-4-nitro-9(10H)-acridinone precursors (1). The annulation of the imidazolo ring onto the aminoacridinone chromophore was accomplished by heating the required aminoacridinone (3) with formic acid or, in the case of 1-methyl derivatives, with N,N-dimethylacetamide. Potent cytotoxic activity against L1210 leukemia, as well as antitumor activity against P388 leukemia in mice, was demonstrated for the 8-hydroxy analogues. The corresponding 8-methoxy derivatives were not cytotoxic. However, in some cases, they showed significant in vivo antileukemic activity.