7-methoxy-4-nitro-1-<<3-propyl>amino>propyl>amino>-9(10H)-acridinone | 166756-58-7

• 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: 7-methoxy-4-nitro-1-<<3-propyl>amino>propyl>amino>-9(10H)-acridinone
• 英文别名: 7-methoxy-1-[3-[methyl-[3-[(4-nitro-9-oxo-10H-acridin-1-yl)amino]propyl]amino]propylamino]-4-nitro-10H-acridin-9-one
• CAS: 166756-58-7
• 化学式: C₃₄H₃₃N₇O₇
• 分子量: 651.679
• InChiKey: WYDMFTLNYGXTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  甲酸 、 7-methoxy-4-nitro-1-<<3-propyl>amino>propyl>amino>-9(10H)-acridinone 在 镍 作用下， 反应 36.0h， 以60%的产率得到8-methoxy-5-<<3-acridin-5-yl)amino>propyl>amino>propyl>amino>-6H-imidazo<4,5,1-de>acridin-6-one
  参考文献：
  名称：

  Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors

  摘要：

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.

  DOI：

  10.1021/jm00016a007
• 作为产物：
  描述：

  N,N-双(3-氨丙基)甲胺 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 9.0h， 生成 7-methoxy-4-nitro-1-<<3-propyl>amino>propyl>amino>-9(10H)-acridinone
  参考文献：
  名称：

  Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors

  摘要：

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.

  DOI：

  10.1021/jm00016a007

文献信息

• Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors
  作者：Wieslaw M. Cholody、Lidia Hernandez、Lawrence Hassner、Dominic A. Scudiero、Draginja B. Djurickovic、Christopher J. Michejda

  DOI：10.1021/jm00016a007

  日期：1995.8

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.