6-chloro-1,3-dimethoxy-7-nitroacridin-9-one | 234107-56-3

• 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: 6-chloro-1,3-dimethoxy-7-nitroacridin-9-one
• 英文别名: 6-chloro-1,3-dimethoxy-7-nitro-10H-acridin-9-one
• CAS: 234107-56-3
• 化学式: C₁₅H₁₁ClN₂O₅
• 分子量: 334.716
• InChiKey: JHDYJMCJXWJOLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-chloro-1,3-dimethoxy-7-nitroacridin-9-one 在 盐酸 、 氢氧化钾 、 18-冠醚-6 、 potassium carbonate 、 tin(ll) chloride 作用下， 反应 14.5h， 生成 7-Amino-6-chloro-10-(2-diethylamino-ethyl)-1,3-dimethoxy-10H-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：

  3-nitro-4-chloro-N-(3,5-dimethoxyphenyl)anthranilic acid 在 PPA 作用下， 反应 2.0h， 以80%的产率得到6-chloro-1,3-dimethoxy-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

• Inhibition of Subgenomic Hepatitis C Virus RNA Replication by Acridone Derivatives: Identification of an NS3 Helicase Inhibitor
  作者：Giuseppe Manfroni、Jan Paeshuyse、Serena Massari、Samantha Zanoli、Barbara Gatto、Giovanni Maga、Oriana Tabarrini、Violetta Cecchetti、Arnaldo Fravolini、Johan Neyts

  DOI：10.1021/jm801608u

  日期：2009.5.28

  We report the synthesis and structure - activity relationship (SAR) of a large series of acridones and acridone-fragment derivatives designed on the basis of the selective antihepatitis C virus (HCV) activity shown by acridone 2, previously studied as a potential antibovine viral diarrhea virus (BVDV) compound. The evaluation of their ability to inhibit the HCV replication in Huh-5-2 cells led to the identification of new, selective inhibitors. This indicates that the acridone skeleton, when properly functionalized, is a suitable scaffold to obtain potential anti-HCV agents. Interestingly, during identification of possible cellular and viral targets, it was discovered that compound 23 exerts inhibitory activity on the HCV NS3 helicase, a very promising target for the development of anti-HCV drugs.
• 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.