1,3-dimethoxy-10-ethyl-6-(4-methyl-1-piperazinyl)-7-nitroacridin-9-one | 234107-61-0

• 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: 1,3-dimethoxy-10-ethyl-6-(4-methyl-1-piperazinyl)-7-nitroacridin-9-one
• 英文别名: 10-Ethyl-1,3-dimethoxy-6-(4-methylpiperazin-1-yl)-7-nitroacridin-9-one
• CAS: 234107-61-0
• 化学式: C₂₂H₂₆N₄O₅
• 分子量: 426.472
• InChiKey: MFIUMNAXUDMXST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-10-ethyl-6-(4-methyl-1-piperazinyl)-7-nitroacridin-9-one 在 盐酸 、 tin(ll) chloride 作用下， 反应 0.5h， 以95%的产率得到7-Amino-10-ethyl-1,3-dimethoxy-6-(4-methylpiperazin-1-yl)acridin-9-one
  参考文献：
  名称：

  Design and Synthesis of Modified Quinolones as Antitumoral Acridones

  摘要：

  The bacterial topoisomerase II (DNA gyrase) and the mammalian topoisomerase II represent the cellular targets for quinolone antibacterials and a wide variety of anticancer drugs, respectively. In view of the mechanistic similarities and sequence homologies exhibited by the two enzymes, tentative efforts to selectively shift from an antibacterial to an antitumoral activity was made by synthesizing a series of modified tricyclic quinolones, in which the essential 3-carboxylic function is surrogated by phenolic OH and the classic C-6 fluorine atom is replaced by a NH2 group. The resulting 7-amino-9-acridone derivatives were assayed, for their antibacterial as well as cytotoxic activities. No antibacterial activity was found. On the other hand, many derivatives showed significant cytotoxic activity against both HL-60 and P388 leukemias and a wide panel of human and rodent solid tumor cells, derivatives 25 and 26 displaying the best overall antiproliferative activity. Against the LoVo cell line, derivative 25 exhibited higher cytotoxic effects than etoposide.

  DOI：

  10.1021/jm980324m
• 作为产物：
  描述：

  6-chloro-1,3-dimethoxy-7-nitroacridin-9-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 1,3-dimethoxy-10-ethyl-6-(4-methyl-1-piperazinyl)-7-nitroacridin-9-one
  参考文献：
  名称：

  Design and Synthesis of Modified Quinolones as Antitumoral Acridones

  摘要：

  The bacterial topoisomerase II (DNA gyrase) and the mammalian topoisomerase II represent the cellular targets for quinolone antibacterials and a wide variety of anticancer drugs, respectively. In view of the mechanistic similarities and sequence homologies exhibited by the two enzymes, tentative efforts to selectively shift from an antibacterial to an antitumoral activity was made by synthesizing a series of modified tricyclic quinolones, in which the essential 3-carboxylic function is surrogated by phenolic OH and the classic C-6 fluorine atom is replaced by a NH2 group. The resulting 7-amino-9-acridone derivatives were assayed, for their antibacterial as well as cytotoxic activities. No antibacterial activity was found. On the other hand, many derivatives showed significant cytotoxic activity against both HL-60 and P388 leukemias and a wide panel of human and rodent solid tumor cells, derivatives 25 and 26 displaying the best overall antiproliferative activity. Against the LoVo cell line, derivative 25 exhibited higher cytotoxic effects than etoposide.

  DOI：

  10.1021/jm980324m

文献信息

• Design and Synthesis of Modified Quinolones as Antitumoral Acridones
  作者：Oriana Tabarrini、Violetta Cecchetti、Arnaldo Fravolini、Giuseppe Nocentini、A. Barzi、Stefano Sabatini、Hua Miao、Claudia Sissi

  DOI：10.1021/jm980324m

  日期：1999.6.1

  The bacterial topoisomerase II (DNA gyrase) and the mammalian topoisomerase II represent the cellular targets for quinolone antibacterials and a wide variety of anticancer drugs, respectively. In view of the mechanistic similarities and sequence homologies exhibited by the two enzymes, tentative efforts to selectively shift from an antibacterial to an antitumoral activity was made by synthesizing a series of modified tricyclic quinolones, in which the essential 3-carboxylic function is surrogated by phenolic OH and the classic C-6 fluorine atom is replaced by a NH2 group. The resulting 7-amino-9-acridone derivatives were assayed, for their antibacterial as well as cytotoxic activities. No antibacterial activity was found. On the other hand, many derivatives showed significant cytotoxic activity against both HL-60 and P388 leukemias and a wide panel of human and rodent solid tumor cells, derivatives 25 and 26 displaying the best overall antiproliferative activity. Against the LoVo cell line, derivative 25 exhibited higher cytotoxic effects than etoposide.