3-(1-(2-bromoacetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one | 1376358-90-5

• 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-bromoacetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
• 英文别名: 3-[2-(2-Bromoacetyl)-3-phenyl-3,4-dihydropyrazol-5-yl]chromen-2-one
• CAS: 1376358-90-5
• 化学式: C₂₀H₁₅BrN₂O₃
• 分子量: 411.255
• InChiKey: KDHPTDYGNNSVRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丁硫醇 、 3-(1-(2-bromoacetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one 在 potassium hydrogencarbonate 、 potassium iodide 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以72%的产率得到3-(1-(2-(butylthio)acetyl)-5-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
• 作为产物：
  描述：

  3-乙酰基香豆素 在 哌啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 3-(1-(2-bromoacetyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  新型3-（1-（2-（2,7a-二氢苯并[d]噻唑-2-基硫基]乙酰基）-5-取代的苯基-4,5-二氢-1H-吡唑-3-基）-香豆素：合成和抗癌活性

  摘要：

  七个新颖的3-（1-（2-（2,7a-二氢苯并[d]噻唑-2-基硫基]乙酰基）-5-取代的苯基-4,5-二氢-1Hyrazol- 3-yl）-2H-色烯合成-2-一衍生物，并通过1 H NMR和13 C NMR进行表征。已经筛选了所有化合物的抗癌活性。生物测定测试表明，化合物4g对人胃癌细胞SGC-7901具有潜在的高活性，IC50值为6.99±1.10μg/ mL。进行对接模拟以将化合物4g置于端粒酶（3DU6）活性位点中，以确定可能的结合模型。

  DOI：

  10.2174/157018012799079743

文献信息

• Novel 3-(1-(2-(2,7a-dihydrobenzo[d]thiazol-2-ylthio)acetyl)-5-substitutedphenyl-4,5-dihydro-1H-pyrazol-3-yl)-Coumarins: Synthesis and Anticancer Activity
  作者：Xian-Hai Lv、Xiu-Li Zhang、Xin-Hua Liu、Lei Shi

  DOI：10.2174/157018012799079743

  日期：2012.2.1

  Seven novel 3-(1-(2-(2,7a-dihydrobenzo[d]thiazol-2-ylthio)acetyl)-5-substituted-phenyl-4,5-dihydro-1Hpyrazol- 3-yl)-2H-chromen-2-one derivatives were synthesized and characterized by 1H NMR and 13 C NMR. All of the compounds have been screened for their anticancer activity. The bioassay tests show that compound 4g exhibited potentially high activity against human gastric cancer cell SGC-7901 with IC50

  七个新颖的3-（1-（2-（2,7a-二氢苯并[d]噻唑-2-基硫基]乙酰基）-5-取代的苯基-4,5-二氢-1Hyrazol- 3-yl）-2H-色烯合成-2-一衍生物，并通过1 H NMR和13 C NMR进行表征。已经筛选了所有化合物的抗癌活性。生物测定测试表明，化合物4g对人胃癌细胞SGC-7901具有潜在的高活性，IC50值为6.99±1.10μg/ mL。进行对接模拟以将化合物4g置于端粒酶（3DU6）活性位点中，以确定可能的结合模型。
• 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.
• 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.