1,3-bis(oxiran-2-ylmethoxy)-10H-acridin-9-one | 1202024-67-6

• 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: 1,3-bis(oxiran-2-ylmethoxy)-10H-acridin-9-one
• CAS: 1202024-67-6
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: HPXFMZRHFJLXIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二羟基-9(10H)-吖啶酮 、 环氧氯丙烷 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 以24.1%的产率得到1,3-bis(oxiran-2-ylmethoxy)-10H-acridin-9-one
  参考文献：
  名称：

  Oxiranylmethyloxy or thiiranylmethyloxy-azaxanthones and -acridone analogues as potential topoisomerase I inhibitors

  摘要：

  A total of seven new oxyranylmethyloxy or thiiranylmethyloxy group substituted 5-azaxanthones and -acridones analogues were synthesized and tested for their biological activities for cancer cell lines and topoisomerases. Among the compounds, compound 5, 3-thiiranylmethyloxy-1-hydroxy-5-azaxanthone, showed effective topoisomerase I inhibitory activity, 50% and 27% inhibition ratio at 100 and 20 mu M, respectively. This result is the first finding of the function of 5-azaxanthone compounds for topoisomerase I inhibition and can provide a novel skeleton for the anticancer drug development process. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.091

文献信息

• Oxiranylmethyloxy or thiiranylmethyloxy-azaxanthones and -acridone analogues as potential topoisomerase I inhibitors
  作者：Hee-Ju Cho、Mi-Ja Jung、Youngjoo Kwon、Younghwa Na

  DOI：10.1016/j.bmcl.2009.09.091

  日期：2009.12

  A total of seven new oxyranylmethyloxy or thiiranylmethyloxy group substituted 5-azaxanthones and -acridones analogues were synthesized and tested for their biological activities for cancer cell lines and topoisomerases. Among the compounds, compound 5, 3-thiiranylmethyloxy-1-hydroxy-5-azaxanthone, showed effective topoisomerase I inhibitory activity, 50% and 27% inhibition ratio at 100 and 20 mu M, respectively. This result is the first finding of the function of 5-azaxanthone compounds for topoisomerase I inhibition and can provide a novel skeleton for the anticancer drug development process. (C) 2009 Elsevier Ltd. All rights reserved.