6-chloro-2-methoxy-N-(3-bromobenzyl)acridin-9-amine | 1447255-31-3

• 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-(3-bromobenzyl)acridin-9-amine
• CAS: 1447255-31-3
• 化学式: C₂₁H₁₆BrClN₂O
• 分子量: 427.728
• InChiKey: MMAWGBKNDWTAKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.15
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-氯-2-(4-甲氧基苯胺基)-苯甲酸 在 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇-D1 为溶剂， 反应 3.75h， 生成 6-chloro-2-methoxy-N-(3-bromobenzyl)acridin-9-amine
  参考文献：
  名称：

  Novel synthetic 9-benzyloxyacridine analogue as both tyrosine kinase and topoisomerase I inhibitor

  摘要：

  Multi-target agents against tyrosine kinases and topoisomerases are potentially useful for the effective treatment of cancers. Discovery of new multi-target scaffolds are important for developing such agents. A series of five novel acridine analogues, LXL 1-5, were synthesized and their antiproliferative activity against HepG-2 cell lines were evaluated, among which the 9-benzyloxyacridine analogue, LXL-5, showed inhibitory activity against tyrosine kinases, VEGFR-2 and Src. The results of UV-visible absorption spectra and fluorescence emission spectra, as well as DNA topoisomerase I inhibition assay, indicated topoisomerase I inhibitory activity. Our study suggested that acridine scaffold, previously shown to have no multi-target kinase and topoisomerase inhibitory activity, might be potentially developed as a multi-target inhibitor of tyrosine kinases and topoisomerase I. (c) 2013 Yu-Yang Jiang and Chun-Mei Gao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.05.018