N-(N-methylpiperidin-4-yl)-9-chloroacridine-4-carboxamide | 1030022-78-6

• 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: N-(N-methylpiperidin-4-yl)-9-chloroacridine-4-carboxamide
• CAS: 1030022-78-6
• 化学式: C₂₀H₂₀ClN₃O
• 分子量: 353.851
• InChiKey: KVBBVMGSFVBFEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(N-methylpiperidin-4-yl)-9-chloroacridine-4-carboxamide 在 氨 作用下， 以 苯酚 为溶剂， 反应 0.5h， 以68%的产率得到9-amino-N-(1-methylpiperidin-4-yl)acridine-4-carboxamide
  参考文献：
  名称：

  DNA threading bis(9-aminoacridine-4-carboxamides): Effects of piperidine sidechains on DNA binding, cytotoxicity and cell cycle arrest

  摘要：

  We describe the synthesis of a series of DNA-threading bis(9-aminoacridine-4-carboxamides) comprising ethylpiperidino and N-methylpiperidin-4-yl sidechains, joined via neutral flexible alkyl chains, charged flexible polyamine chains and a semi-rigid charged piperazine linker. Their cytotoxicity towards human leukaemic cells gives IC50 values ranging from 99 to 1100 nM, with the ethylpiperidino series generally being more cytotoxic than the N-methylpiperidin-4-yl series. Measurements with supercoiled DNA indicate that they bisintercalate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.063
• 作为产物：
  描述：

  4-氨基-1-甲基哌啶 、 9-chloroacridine-4-carbonyl chloride 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以0.4 g的产率得到N-(N-methylpiperidin-4-yl)-9-chloroacridine-4-carboxamide
  参考文献：
  名称：

  DNA threading bis(9-aminoacridine-4-carboxamides): Effects of piperidine sidechains on DNA binding, cytotoxicity and cell cycle arrest

  摘要：

  We describe the synthesis of a series of DNA-threading bis(9-aminoacridine-4-carboxamides) comprising ethylpiperidino and N-methylpiperidin-4-yl sidechains, joined via neutral flexible alkyl chains, charged flexible polyamine chains and a semi-rigid charged piperazine linker. Their cytotoxicity towards human leukaemic cells gives IC50 values ranging from 99 to 1100 nM, with the ethylpiperidino series generally being more cytotoxic than the N-methylpiperidin-4-yl series. Measurements with supercoiled DNA indicate that they bisintercalate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.063