10-[[3,5-Bis(phenylmethoxy)phenyl]methyl]acridin-9-one | 1073142-67-2

• 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: 10-[[3,5-Bis(phenylmethoxy)phenyl]methyl]acridin-9-one
• CAS: 1073142-67-2
• 化学式: C₃₄H₂₇NO₃
• 分子量: 497.593
• InChiKey: WKKATJBENFZAOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-dibenzyloxybenzyl chloride 、 吖啶酮 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到10-[[3,5-Bis(phenylmethoxy)phenyl]methyl]acridin-9-one
  参考文献：
  名称：

  Synthesis and potent antileukemic activities of 10-benzyl-9(10H)-acridinones

  摘要：

  A novel series of 10-benzyl-9(10H)-acridinones and 1-benzyl-4-piperidones were synthesized and tested for their in vitro antitumor activities against CCRF-CEM cells. Assay-based antiproliferative activity study using CCRF-CEM cell lines revealed that the acridone group and the substitution pattern on the benzene unit had significant effect on cytotoxicity of this series of compounds, among which 10-(3,5-dimethoxy) benzyl-9(10H)-acridinone (3b) was found to be the most active compound with IC(50) at about 0.7 mu M. Compound 3b was also found to have antiproliferative activity against two other human leukemic cell lines K562 and HL60 using the MTT assay. The antitumor effect of 3b is believed to be due to the induction of apoptosis, which is further confirmed by PI ( Propidium iodide) staining and Annexin V-FITC/PI staining assay using flow cytometry analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.086

文献信息

• Synthesis and potent antileukemic activities of 10-benzyl-9(10H)-acridinones
  作者：Chunmei Gao、Yuyang Jiang、Chunyan Tan、Xuyu Zu、Huachen Liu、Derong Cao

  DOI：10.1016/j.bmc.2008.07.086

  日期：2008.9

  A novel series of 10-benzyl-9(10H)-acridinones and 1-benzyl-4-piperidones were synthesized and tested for their in vitro antitumor activities against CCRF-CEM cells. Assay-based antiproliferative activity study using CCRF-CEM cell lines revealed that the acridone group and the substitution pattern on the benzene unit had significant effect on cytotoxicity of this series of compounds, among which 10-(3,5-dimethoxy) benzyl-9(10H)-acridinone (3b) was found to be the most active compound with IC(50) at about 0.7 mu M. Compound 3b was also found to have antiproliferative activity against two other human leukemic cell lines K562 and HL60 using the MTT assay. The antitumor effect of 3b is believed to be due to the induction of apoptosis, which is further confirmed by PI ( Propidium iodide) staining and Annexin V-FITC/PI staining assay using flow cytometry analysis. (C) 2008 Elsevier Ltd. All rights reserved.