6-chloro-2-methoxy-N-[2-(piperazin-1-yl)ethyl]acridin-9-amine | 86863-23-2

• 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-2-methoxy-N-[2-(piperazin-1-yl)ethyl]acridin-9-amine
• 英文别名: 6-chloro-2-methoxy-N-[2-(piperazin-1-yl)ethyl]acridin-9-ylamine；9-Acridinamine, 6-chloro-2-methoxy-N-(2-(1-piperazinyl)ethyl)-；6-chloro-2-methoxy-N-(2-piperazin-1-ylethyl)acridin-9-amine
• CAS: 86863-23-2
• 化学式: C₂₀H₂₃ClN₄O
• 分子量: 370.882
• InChiKey: UQRORLSMRFANID-UHFFFAOYSA-N

物化性质

• 沸点：
  590.9±50.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-2-methoxy-N-[2-(piperazin-1-yl)ethyl]acridin-9-amine 、 2-(10β-dihydroartemisinoxy)propyl bromide 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 45.0 ℃ 、344.75 kPa 条件下， 反应 0.17h， 以71%的产率得到6-chloro-2-methoxy-N-[2-(piperazin-1-yl)ethyl]acridin-9-amine-2-(10β-dihydroartemisinoxy)ethane
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of aminoacridines and artemisinin–acridine hybrids

  摘要：

  During this study, 9-aminoacridine and artemisinin-acridine hybrid compounds were synthesized and the in vitro for antimalarial activity against both the chloroquine sensitive but also gametocytocidal strain (NF54), and chloroquine resistant (Dd2) strains of Plasmodium fakiparum was determined. In vitro cytotoxicity against CHO cells, apoptosis of HepG2 and SH-SY5Y as well as anticancer activity against HeLa cell lines were assessed. The hybrids were synthesized, using a microwave-assisted radiation method by covalently linking artemisinin and acridine pharmacophores by means of a liable, aminoethyl ether linker. The synthesized compounds were found active against both the Plasmodium strains and displayed superior selective toxicity towards the parasitic cells. Hybrid 7, however, containing ethylenediamine linker, proved the most active of all of the synthesized compounds. It had seven-fold higher antigametocytocidal activity compared to chloroquine and was also found to be seven-fold more potent than chloroquine against the Dd2 strain, with highly selective action towards the parasitic cells. This hybrid also showed favourable anti-cancer activity against the HeLa cells, three-and eight-fold higher than those of chloroquine and melphalan, respectively. This hybrid may therefore stand as drug candidate for further investigation in the search for new and effective drugs against malaria and cervical cancer. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2014.01.014
• 作为产物：
  描述：

  N-氨乙基哌嗪 、 6,9-二氯-2-甲氧基吖啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到6-chloro-2-methoxy-N-[2-(piperazin-1-yl)ethyl]acridin-9-amine
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of aminoacridines and artemisinin–acridine hybrids

  摘要：

  During this study, 9-aminoacridine and artemisinin-acridine hybrid compounds were synthesized and the in vitro for antimalarial activity against both the chloroquine sensitive but also gametocytocidal strain (NF54), and chloroquine resistant (Dd2) strains of Plasmodium fakiparum was determined. In vitro cytotoxicity against CHO cells, apoptosis of HepG2 and SH-SY5Y as well as anticancer activity against HeLa cell lines were assessed. The hybrids were synthesized, using a microwave-assisted radiation method by covalently linking artemisinin and acridine pharmacophores by means of a liable, aminoethyl ether linker. The synthesized compounds were found active against both the Plasmodium strains and displayed superior selective toxicity towards the parasitic cells. Hybrid 7, however, containing ethylenediamine linker, proved the most active of all of the synthesized compounds. It had seven-fold higher antigametocytocidal activity compared to chloroquine and was also found to be seven-fold more potent than chloroquine against the Dd2 strain, with highly selective action towards the parasitic cells. This hybrid also showed favourable anti-cancer activity against the HeLa cells, three-and eight-fold higher than those of chloroquine and melphalan, respectively. This hybrid may therefore stand as drug candidate for further investigation in the search for new and effective drugs against malaria and cervical cancer. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2014.01.014

文献信息

• Synthesis and in vitro biological evaluation of aminoacridines and artemisinin–acridine hybrids
  作者：Juan P. Joubert、Frans J. Smit、Lissinda du Plessis、Peter J. Smith、David D. N’Da

  DOI：10.1016/j.ejps.2014.01.014

  日期：2014.6

  During this study, 9-aminoacridine and artemisinin-acridine hybrid compounds were synthesized and the in vitro for antimalarial activity against both the chloroquine sensitive but also gametocytocidal strain (NF54), and chloroquine resistant (Dd2) strains of Plasmodium fakiparum was determined. In vitro cytotoxicity against CHO cells, apoptosis of HepG2 and SH-SY5Y as well as anticancer activity against HeLa cell lines were assessed. The hybrids were synthesized, using a microwave-assisted radiation method by covalently linking artemisinin and acridine pharmacophores by means of a liable, aminoethyl ether linker. The synthesized compounds were found active against both the Plasmodium strains and displayed superior selective toxicity towards the parasitic cells. Hybrid 7, however, containing ethylenediamine linker, proved the most active of all of the synthesized compounds. It had seven-fold higher antigametocytocidal activity compared to chloroquine and was also found to be seven-fold more potent than chloroquine against the Dd2 strain, with highly selective action towards the parasitic cells. This hybrid also showed favourable anti-cancer activity against the HeLa cells, three-and eight-fold higher than those of chloroquine and melphalan, respectively. This hybrid may therefore stand as drug candidate for further investigation in the search for new and effective drugs against malaria and cervical cancer. (C) 2014 Elsevier B.V. All rights reserved.