10-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 10-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one
• 英文别名: 5-[[1-[(4-fluorophenyl)methyl]triazol-4-yl]methyl]-11H-benzo[b][1,4]benzodiazepin-6-one
• 化学式: C₂₃H₁₈FN₅O
• 分子量: 399.427
• InChiKey: OQWFEEXCSSYPKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘苯甲酸乙酯, 在 potassium phosphate 、 copper(l) iodide 、 正丁基锂 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 乙二醇 、 叔丁醇 为溶剂， 反应 0.08h， 生成 10-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 5,10-dihydro-11 H -dibenzo[ b,e ][1,4]diazepin-11-one structural derivatives as anti-cancer and apoptosis inducing agents

  摘要：

  A series of thirteen 5H-dibenzo [b,e][1,4]diazepin-11(10H)-one structural derivatives has been synthesized and evaluated for anti-proliferative activity against five human cancer cell lines. Compound 9a exhibited potent tumour growth inhibition in all cell lines with IC50 values in the range of 0.71-7.29 mu M. Experiments on lung (A549) and breast (MDAMB-231) cancer cell lines to investigate the mechanisms of growth inhibition and apoptosis inducing effects of 9a showed that it arrested both cancer cell lines in the G2/M phase of cell cycle in a dose dependent manner. Hoechst staining analysis revealed that 9a inhibited tumour cell proliferation through apoptosis induction. Additionally, the mitochondria! membrane potential (Delta Psi m) was affected and the levels of reactive oxygen species (ROS) were raised. The simple synthetic preparation and their biological properties make these dibenzodiazepinone-triazole scaffolds promising new entities for the development of cancer therapeutics. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.007

文献信息

• Synthesis and biological evaluation of 5,10-dihydro-11 H -dibenzo[ b,e ][1,4]diazepin-11-one structural derivatives as anti-cancer and apoptosis inducing agents
  作者：Chintakunta Praveen Kumar、T. Srinivasa Reddy、Prathama S. Mainkar、Vipul Bansal、Ravi Shukla、Srivari Chandrasekhar、Helmut M. Hügel

  DOI：10.1016/j.ejmech.2015.12.007

  日期：2016.1

  A series of thirteen 5H-dibenzo [b,e][1,4]diazepin-11(10H)-one structural derivatives has been synthesized and evaluated for anti-proliferative activity against five human cancer cell lines. Compound 9a exhibited potent tumour growth inhibition in all cell lines with IC50 values in the range of 0.71-7.29 mu M. Experiments on lung (A549) and breast (MDAMB-231) cancer cell lines to investigate the mechanisms of growth inhibition and apoptosis inducing effects of 9a showed that it arrested both cancer cell lines in the G2/M phase of cell cycle in a dose dependent manner. Hoechst staining analysis revealed that 9a inhibited tumour cell proliferation through apoptosis induction. Additionally, the mitochondria! membrane potential (Delta Psi m) was affected and the levels of reactive oxygen species (ROS) were raised. The simple synthetic preparation and their biological properties make these dibenzodiazepinone-triazole scaffolds promising new entities for the development of cancer therapeutics. (C) 2015 Elsevier Masson SAS. All rights reserved.