N,N-bis{4-[N-(N-methylpiperidin-4-yl)carbamoyl]acridin-9-yl}-[1,4-bis(2-aminoethyl)-piperazine] | 1030022-76-4

• 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: N,N-bis{4-[N-(N-methylpiperidin-4-yl)carbamoyl]acridin-9-yl}-[1,4-bis(2-aminoethyl)-piperazine]
• 英文别名: N-(1-methylpiperidin-4-yl)-9-[2-[4-[2-[[4-[(1-methylpiperidin-4-yl)carbamoyl]acridin-9-yl]amino]ethyl]piperazin-1-yl]ethylamino]acridine-4-carboxamide
• CAS: 1030022-76-4
• 化学式: C₄₈H₅₈N₁₀O₂
• 分子量: 807.054
• InChiKey: CGMAXJNYFHHJAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  60
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,4-哌嗪二乙胺 、 N-(N-methylpiperidin-4-yl)-9-chloroacridine-4-carboxamide 以 苯酚 为溶剂， 反应 2.0h， 以35%的产率得到N,N-bis{4-[N-(N-methylpiperidin-4-yl)carbamoyl]acridin-9-yl}-[1,4-bis(2-aminoethyl)-piperazine]
  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

文献信息

• DNA threading bis(9-aminoacridine-4-carboxamides): Effects of piperidine sidechains on DNA binding, cytotoxicity and cell cycle arrest
  作者：Zhicong He、Xianyong Bu、Alexandra Eleftheriou、Malik Zihlif、Zhang Qing、Bernard W. Stewart、Laurence P.G. Wakelin

  DOI：10.1016/j.bmc.2008.02.063

  日期：2008.4

  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.