3-(1-(2-(4-bromopiperidin-1-yl)acetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one | 1376358-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(1-(2-(4-bromopiperidin-1-yl)acetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
• 英文别名: 3-[2-[2-(4-Bromopiperidin-1-yl)acetyl]-3-phenyl-3,4-dihydropyrazol-5-yl]chromen-2-one
• CAS: 1376358-84-7
• 化学式: C₂₅H₂₄BrN₃O₃
• 分子量: 494.388
• InChiKey: VJEPHVLSTZWVKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-cinnamoyl-2H-chromen-2-one 在 4-二甲氨基吡啶 、 一水合肼 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.0h， 生成 3-(1-(2-(4-bromopiperidin-1-yl)acetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Design and synthesis of novel 5-phenyl-N-piperidine ethanone containing 4,5-dihydropyrazole derivatives as potential antitumor agents

  摘要：

  A series of novel 5-phenyl-N-piperidine ethanone-4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassays demonstrated that compounds 4d, 4f, 7a and 7h occupied high antiproliferative activities against SGC-7901, MGC-803 and Bcap-37 cell lines. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 7b showed the most potent inhibitory activity with IC50 value at 2.00 +/- 0.40 mu M. The active compound 4d was also docked into the telomerase TERT active site to determine the probable binding model. The results indicated that conserved residues Lys189, Asp254 and Gln308 were important for ligand binding via hydrogen bond interactions. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.040

文献信息

• Design and synthesis of novel 5-phenyl-N-piperidine ethanone containing 4,5-dihydropyrazole derivatives as potential antitumor agents
  作者：Xin-Hua Liu、Jun Li、Jing Bo Shi、Bao-An Song、Xing-Bao Qi

  DOI：10.1016/j.ejmech.2012.02.040

  日期：2012.5

  A series of novel 5-phenyl-N-piperidine ethanone-4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassays demonstrated that compounds 4d, 4f, 7a and 7h occupied high antiproliferative activities against SGC-7901, MGC-803 and Bcap-37 cell lines. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 7b showed the most potent inhibitory activity with IC50 value at 2.00 +/- 0.40 mu M. The active compound 4d was also docked into the telomerase TERT active site to determine the probable binding model. The results indicated that conserved residues Lys189, Asp254 and Gln308 were important for ligand binding via hydrogen bond interactions. (C) 2012 Elsevier Masson SAS. All rights reserved.