10-(4-Chlorobutyl)-4-methoxyacridin-9-one | 692776-84-4

• 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: 10-(4-Chlorobutyl)-4-methoxyacridin-9-one
• CAS: 692776-84-4
• 化学式: C₁₈H₁₈ClNO₂
• 分子量: 315.799
• InChiKey: STXRGRURFZUNSD-UHFFFAOYSA-N

物化性质

• 沸点：
  492.8±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 10-(4-Chlorobutyl)-4-methoxyacridin-9-one 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以57%的产率得到4-Methoxy-10-[4-(4-methylpiperazin-1-yl)butyl]acridin-9-one
  参考文献：
  名称：

  Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells

  摘要：

  Multidrug resistance (MDR) is one of the main obstacles limiting the efficacy of chemotherapy treatment of tumors. Parent acridones 1A and 1B were prepared by the Ullmann reaction followed by cyclization and N-alkylation. N-(omega-Chloroalkyl) analogues were subjected to iodide catalyzed nucleophilic Substitution reaction with secondary amines to get the compounds 3A-13A and 3B-13B, which enhanced the uptake of vinblastine in KBCh(R)-8-5 cells to a greater extent (2.6-13.1-fold relative to control) than verapamil. The study oil the structure-activity relationship revealed that substitution of -H at position C-4 in acridone nucleus by -OCH3 increased the cytotoxic and anti-MDR activities. The ability of acridones to inhibit calmodulin dependent cyclic AMP phosphodiesterase has been determined and the results have shown a strong positive correlation between anti-calmodulin activity and cytotoxicity in KBCh(R)-8-5 cells or anti-MDR activity. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.001
• 作为产物：
  描述：

  2-[(2-甲氧基苯基)氨基]-苯甲酸 在 氢氧化钾 、 PPA 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 生成 10-(4-Chlorobutyl)-4-methoxyacridin-9-one
  参考文献：
  名称：

  Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells

  摘要：

  Multidrug resistance (MDR) is one of the main obstacles limiting the efficacy of chemotherapy treatment of tumors. Parent acridones 1A and 1B were prepared by the Ullmann reaction followed by cyclization and N-alkylation. N-(omega-Chloroalkyl) analogues were subjected to iodide catalyzed nucleophilic Substitution reaction with secondary amines to get the compounds 3A-13A and 3B-13B, which enhanced the uptake of vinblastine in KBCh(R)-8-5 cells to a greater extent (2.6-13.1-fold relative to control) than verapamil. The study oil the structure-activity relationship revealed that substitution of -H at position C-4 in acridone nucleus by -OCH3 increased the cytotoxic and anti-MDR activities. The ability of acridones to inhibit calmodulin dependent cyclic AMP phosphodiesterase has been determined and the results have shown a strong positive correlation between anti-calmodulin activity and cytotoxicity in KBCh(R)-8-5 cells or anti-MDR activity. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.001

文献信息

• Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells
  作者：Ravi Hegde、Padma Thimmaiah、Mayur C Yerigeri、Gowdahalli Krishnegowda、Kuntebommanahalli N Thimmaiah、Peter J Houghton

  DOI：10.1016/j.ejmech.2003.12.001

  日期：2004.2

  Multidrug resistance (MDR) is one of the main obstacles limiting the efficacy of chemotherapy treatment of tumors. Parent acridones 1A and 1B were prepared by the Ullmann reaction followed by cyclization and N-alkylation. N-(omega-Chloroalkyl) analogues were subjected to iodide catalyzed nucleophilic Substitution reaction with secondary amines to get the compounds 3A-13A and 3B-13B, which enhanced the uptake of vinblastine in KBCh(R)-8-5 cells to a greater extent (2.6-13.1-fold relative to control) than verapamil. The study oil the structure-activity relationship revealed that substitution of -H at position C-4 in acridone nucleus by -OCH3 increased the cytotoxic and anti-MDR activities. The ability of acridones to inhibit calmodulin dependent cyclic AMP phosphodiesterase has been determined and the results have shown a strong positive correlation between anti-calmodulin activity and cytotoxicity in KBCh(R)-8-5 cells or anti-MDR activity. (C) 2003 Elsevier SAS. All rights reserved.