6-(2-Dimethylamino-ethyl)-10-methoxy-2-(2-piperidin-1-yl-ethyl)-2H-1,2,6,7a-tetraaza-benzo[fg]aceanthrylene-5,7-dione

• 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-(2-Dimethylamino-ethyl)-10-methoxy-2-(2-piperidin-1-yl-ethyl)-2H-1,2,6,7a-tetraaza-benzo[fg]aceanthrylene-5,7-dione
• 英文别名: 16-[2-(Dimethylamino)ethyl]-5-methoxy-10-(2-piperidin-1-ylethyl)-1,9,10,16-tetrazapentacyclo[9.6.2.02,7.08,19.014,18]nonadeca-2(7),3,5,8,11(19),12,14(18)-heptaene-15,17-dione
• 化学式: C₂₇H₃₂N₆O₃
• 分子量: 488.589
• InChiKey: KGDVVAWJEOXWQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  光气 、 9-Methoxy-2-(2-piperidin-1-yl-ethyl)-2,6-dihydro-pyrazolo[3,4,5-kl]acridine-5-carboxylic acid (2-dimethylamino-ethyl)-amide; compound with GENERIC INORGANIC NEUTRAL COMPONENT 在 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 0.33h， 以39%的产率得到6-(2-Dimethylamino-ethyl)-10-methoxy-2-(2-piperidin-1-yl-ethyl)-2H-1,2,6,7a-tetraaza-benzo[fg]aceanthrylene-5,7-dione
  参考文献：
  名称：

  2,6-Di(ω-aminoalkyl)-2,5,6,7-tetrahydropyrazolo[3,4,5-mn]pyrimido[5,6,1-de]acridine-5,7-diones:  Novel, Potent, Cytotoxic, and DNA-Binding Agents

  摘要：

  DNA-binding agents with potential antitumor activities bearing two cationic side chains, the 2,6-di(omega-aminoalkyl)-2,5,6,7-tetrahydropyrazolo[3,4,5-mn]pyrimido[5,6,1-de]acridine-5,7-diones (4a-r), have been prepared either by reaction of the appropriate 2-(omega-aminoalkyl)-6-chloro-2,3-dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione with the appropriate (omega-aminoalkyl)hydrazine or by cyclization of the requisite N-6,2-di(omega-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl]acridine-6-carboxamide with phosgene. In vitro cytotoxic properties of these derivatives against three human colon adenocarcinoma cell lines (HT29, LoVo, and LoVo/Dx) and against some cell lines of the NCI panel are described and compared to that of reference drugs. Some of the new compounds showed outstanding potency while lacking cross-resistance with anthracyclines. Structure-activity relationships are discussed, and a mechanistic analysis is performed using the COMPARE procedure. The mechanism and efficiency of noncovalent DNA binding of these compounds are examined using gel electrophoresis and fluorometric techniques. The 2,6-di(omega-aminoalkyl)-2,5,6,7-tetrahydropyrazolo[3,4,5-mn]pyrimido[5,6,1-de]acridine-5,7-diones (4) constitute a new class of potent, cytotoxic DNA-binding agents not cross-resistant with doxorubicin.

  DOI：

  10.1021/jm011004x