5-<<2-(diethylamino)ethyl>amino>-8-methoxy-1-methyl-6H-imidazo<4,5,1-de>acridin-6-one dihydrochloride | 138154-48-0

• 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: 5-<<2-(diethylamino)ethyl>amino>-8-methoxy-1-methyl-6H-imidazo<4,5,1-de>acridin-6-one dihydrochloride
• 英文别名: NSC 637993；10-[2-(Diethylamino)ethylamino]-5-methoxy-15-methyl-1,14-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-2(7),3,5,9,11,13(16),14-heptaen-8-one;hydrochloride
• CAS: 138154-48-0
• 化学式: C₂₂H₂₆N₄O₂*2ClH
• 分子量: 451.396
• InChiKey: GYDUKVCOVDBXKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-二甲基乙酰胺 、 反应 12.0h， 以70%的产率得到5-<<2-(diethylamino)ethyl>amino>-8-methoxy-1-methyl-6H-imidazo<4,5,1-de>acridin-6-one dihydrochloride
  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

• EGR1 TARGETING MOLECULES FOR THE TREATMENT OF INFLAMMATORY AND HYPERPROLIFERATIVE CONDITIONS
  申请人：The Medical Research, Infrastructure and Health Services Fund of the Tel Aviv Medical Center

  公开号：US20180289728A1

  公开（公告）日：2018-10-11

  A method of treating an inflammation or a hyperproliferative disease in a subject in need thereof is disclosed. The method comprising administering to the subject a therapeutically effective amount of a compound selected from the group consisting of: a compound represented by Formula I: or a pharmaceutically acceptable salt thereof, a compound represented by Formula II: and a compound represented by Formula III: wherein the variables in Formulae I, II and III are as defined in the specification.
• 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.