3-(1-(2-(butylthio)acetyl)-5-(2-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one

• 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-(butylthio)acetyl)-5-(2-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
• 化学式: C₂₅H₂₃F₃N₂O₃S
• 分子量: 488.53
• InChiKey: SYDQRTAHHKBFID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  62.88
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-[3-[2-(trifluoromethyl)phenyl]prop-2-enoyl]chromen-2-one 在 potassium hydrogencarbonate 、 一水合肼 、 potassium iodide 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 3-(1-(2-(butylthio)acetyl)-5-(2-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Novel coumarin-dihydropyrazole thio-ethanone derivatives: Design, synthesis and anticancer activity

  摘要：

  A series novel 1-(3-substituted-5-pheny1-4,5-dihydropyrazol-1-y1)-2-thio-ethanone derivatives as potential telomerase inhibitors were designed and synthesized. The bioassays demonstrated that compounds 4a, 4f, 4j and 7b, 7d occupied high antiproliferative activity against SGC-7901, MGC-803, Bcap-37 and HEPG-2 cell lines. By a modified TRAP assay, some title compounds were tested against telomerase, and compound 4f showed the most potent inhibitory activity with IC50 value at 0.92 +/- 0.09 mu M. The mechanism of antitumor action indicated that title compounds 4f and 7b could suppress cell proliferation through inducing cell cycle arrest in G0/G1 phase. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.014

文献信息

• Novel coumarin-dihydropyrazole thio-ethanone derivatives: Design, synthesis and anticancer activity
  作者：Xiao-Qin Wu、Cheng Huang、Ying-Ming Jia、Bao-An Song、Jun Li、Xin-Hua Liu

  DOI：10.1016/j.ejmech.2013.06.014

  日期：2014.3

  A series novel 1-(3-substituted-5-pheny1-4,5-dihydropyrazol-1-y1)-2-thio-ethanone derivatives as potential telomerase inhibitors were designed and synthesized. The bioassays demonstrated that compounds 4a, 4f, 4j and 7b, 7d occupied high antiproliferative activity against SGC-7901, MGC-803, Bcap-37 and HEPG-2 cell lines. By a modified TRAP assay, some title compounds were tested against telomerase, and compound 4f showed the most potent inhibitory activity with IC50 value at 0.92 +/- 0.09 mu M. The mechanism of antitumor action indicated that title compounds 4f and 7b could suppress cell proliferation through inducing cell cycle arrest in G0/G1 phase. (C) 2013 Elsevier Masson SAS. All rights reserved.