1-<<2-(diethylamino)ethyl>amino>-7-methoxy-4-nitro-9(10H)-acridinone | 99139-89-6

• 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: 1-<<2-(diethylamino)ethyl>amino>-7-methoxy-4-nitro-9(10H)-acridinone
• 英文别名: 1-[[2-(diethylamino)ethyl]amino]-7-methoxy-4-nitro-9(10H)-acridinone；1-[2-(diethylamino)ethylamino]-7-methoxy-4-nitro-10H-acridin-9-one
• CAS: 99139-89-6
• 化学式: C₂₀H₂₄N₄O₄
• 分子量: 384.435
• InChiKey: HGCUZKFNPOOGSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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-<<2-(diethylamino)ethyl>amino>-7-methoxy-4-nitro-9(10H)-acridinone 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-(2-diethylamino-ethylamino)-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-二乙基乙二胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以92%的产率得到1-<<2-(diethylamino)ethyl>amino>-7-methoxy-4-nitro-9(10H)-acridinone
  参考文献：
  名称：

  Imidazoacridinone derivative compounds and methods for their use

  摘要：

  本发明提供了公式为的IA衍生物化合物：其中变量如本文所述。

  公开号：

  US20100137351A1

文献信息

• Imidazoacridinone derivative compounds and methods for their use
  申请人：Assaraf Yehuda G.

  公开号：US20100137351A1

  公开（公告）日：2010-06-03

  The present invention provides IA derivative compounds of the formula: where the variables are described herein.

  本发明提供了公式为的IA衍生物化合物：其中变量如本文所述。
• Substituted 1-amino-4-nitro-acridinones, pharmaceutical compositions comprising the same and processes for their production
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0145226A2

  公开（公告）日：1985-06-19

  Substituted 1-Amino-4-nitroacridinones of formula as antibacterial and antitumor agents are herein described. Also disclosed are processes for their production and pharmaceutical compositions comprising the new compounds.

  式中的取代的 1-氨基-4-硝基吖啶酮作为抗菌剂和抗肿瘤剂在此被描述。 作为抗菌剂和抗肿瘤剂。此外，还公开了其生产工艺和包含这些新化合物的药物组合物。
• Imidazoacridines and their antineoplastic use
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：EP0502668A1

  公开（公告）日：1992-09-09

  Compounds of formula I in which:    R represents: -OH or -OR′, wherein R′ represents C₁-C₆ alkyl,    R₁a and R₁b, which may be identical or different, represent hydrogen or C₁-C₆ alkyl, unsubstituted or substituted by a hydroxyl, an amino, a N′-alkylamino or a N′,N′-dialkylamino group, such N′-alkyl groups containing 1-4 carbon atoms,    n is 2-5 and    R₂ represents hydrogen, or straight chain C₁₋₄ alkyl, in the form of a free base or a pharmaceutically acceptable acid addition salt or an N-oxide are useful in antineoplastic treatment and prophylaxis, especially of leukaemias.

  式 I 的化合物 其中 R 代表-OH或-OR′，其中R′代表C₁-C₆烷基、 R₁a 和 R₁b 可以相同或不同，代表氢或 C₁-C₆ 烷基，未被羟基、氨基、N′-烷基氨基或 N′,N′-二烷基氨基取代或取代，此类 N′-烷基含有 1-4 个碳原子、 n 为 2-5 R₂ 代表氢或直链 C₁₋₄ 烷基、 以游离碱或药学上可接受的酸加成盐或 N-氧化物的形式存在，可用于抗肿瘤治疗和预防，尤其是白血病。
• US4626540A
  申请人：——

  公开号：US4626540A

  公开（公告）日：1986-12-02
• US8470844B2
  申请人：——

  公开号：US8470844B2

  公开（公告）日：2013-06-25