1-hydroxy-3-(4-(piperidin-1-yl)butoxy)-9H-xanthen-9-one | 1595287-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-hydroxy-3-(4-(piperidin-1-yl)butoxy)-9H-xanthen-9-one
• 英文别名: 1-Hydroxy-3-(4-piperidin-1-ylbutoxy)xanthen-9-one；1-hydroxy-3-(4-piperidin-1-ylbutoxy)xanthen-9-one
• CAS: 1595287-83-4
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: RIGZGPBVKWAXGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3-(4-(piperidin-1-yl)butoxy)-9H-xanthen-9-one 、 碘甲烷 以 氯仿 为溶剂， 反应 72.0h， 以89%的产率得到1-(4-(1-hydroxy-9-oxo-9H-xanthen-3-yloxy)butyl)-1-methylpiperidinium iodide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives as potent anticancer agents

  摘要：

  A series of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives were designed, synthesized and evaluated for in vitro anticancer activity against four selected human cancer cell lines (nasopharyngeal neoplasm CNE, liver cancer BEL-7402, gastric cancer MGC-803, lung adenocarcinoma A549). Most of the synthesized compounds exhibit effective cytotoxic activity against the four tested cancer cell lines with the IC50 values at micromolar concentration level. Some preliminary structure activity relationships were also discussed. In this series of derivatives, compound 3g shows excellent broad spectrum anticancer activity with IC50 values ranging from 3.57 to 20.07 mu M. The in vitro anticancer activity effect and action mechanism of compound 3g on human gastric carcinoma MGC-803 cell were further investigated. The results showed that compound 3g exhibits dose- and time-dependent anticancer effects on MGC-803 cells through apoptosis, which might be associated with its decreasing intracellular calcium and the mitochondrial membrane potential. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.076
• 作为产物：
  描述：

  水杨酸 在 potassium carbonate 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 26.5h， 生成 1-hydroxy-3-(4-(piperidin-1-yl)butoxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives as potent anticancer agents

  摘要：

  A series of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives were designed, synthesized and evaluated for in vitro anticancer activity against four selected human cancer cell lines (nasopharyngeal neoplasm CNE, liver cancer BEL-7402, gastric cancer MGC-803, lung adenocarcinoma A549). Most of the synthesized compounds exhibit effective cytotoxic activity against the four tested cancer cell lines with the IC50 values at micromolar concentration level. Some preliminary structure activity relationships were also discussed. In this series of derivatives, compound 3g shows excellent broad spectrum anticancer activity with IC50 values ranging from 3.57 to 20.07 mu M. The in vitro anticancer activity effect and action mechanism of compound 3g on human gastric carcinoma MGC-803 cell were further investigated. The results showed that compound 3g exhibits dose- and time-dependent anticancer effects on MGC-803 cells through apoptosis, which might be associated with its decreasing intracellular calcium and the mitochondrial membrane potential. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.076

文献信息

• Design, synthesis and biological evaluation of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives as potent anticancer agents
  作者：Zheng-Min Yang、Jun Huang、Jiang-Ke Qin、Zhi-Kai Dai、Wen-Li Lan、Gui-Fa Su、Huang Tang、Feng Yang

  DOI：10.1016/j.ejmech.2014.07.076

  日期：2014.10

  A series of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives were designed, synthesized and evaluated for in vitro anticancer activity against four selected human cancer cell lines (nasopharyngeal neoplasm CNE, liver cancer BEL-7402, gastric cancer MGC-803, lung adenocarcinoma A549). Most of the synthesized compounds exhibit effective cytotoxic activity against the four tested cancer cell lines with the IC50 values at micromolar concentration level. Some preliminary structure activity relationships were also discussed. In this series of derivatives, compound 3g shows excellent broad spectrum anticancer activity with IC50 values ranging from 3.57 to 20.07 mu M. The in vitro anticancer activity effect and action mechanism of compound 3g on human gastric carcinoma MGC-803 cell were further investigated. The results showed that compound 3g exhibits dose- and time-dependent anticancer effects on MGC-803 cells through apoptosis, which might be associated with its decreasing intracellular calcium and the mitochondrial membrane potential. (C) 2014 Elsevier Masson SAS. All rights reserved.