3-methyl-1-phenyl-4-[(4-phenylphenyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-one | 413591-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-1-phenyl-4-[(4-phenylphenyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-one
• 英文别名: 4-(biphenyl-4-carbonyl)-3-methyl-1-phenyl-5-pyrazolone；4-(biphenyl-4-ylcarbonyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one；5-methyl-2-phenyl-4-(4-phenylbenzoyl)-4H-pyrazol-3-one
• CAS: 413591-36-3
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: ICTRNWORWUHRTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-1-phenyl-4-[(4-phenylphenyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-one 以 乙醇 、 甲苯 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Ring-opening polymerization ofl-lactide catalyzed by calcium complexes

  摘要：

  我们合成并鉴定了一系列由 NNO-三叉酮亚胺配体支持的钙络合物。X 射线结构研究表明，这些配合物具有单核特征，六配位钙中心与两个酮亚胺配体成键。在这些配合物的催化下，L-内酰胺的聚合反应在多种醇类存在的情况下均能快速进行，且控制良好。此外，即使添加多达 80 等量的苯甲醇作为转移剂，这些复合物也能显示出良好的催化活性。此外，动力学研究表明，L-内酰胺的 ROP 与 [LA] 呈一阶依赖关系，与 [BnOH] 呈二阶依赖关系。

  DOI：

  10.1039/c2dt32487c
• 作为产物：
  描述：

  联苯-4-甲酰氯 、 依达拉奉 在 calcium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.5h， 以80%的产率得到3-methyl-1-phenyl-4-[(4-phenylphenyl)carbonyl]-4,5-dihydro-1H-pyrazol-5-one
  参考文献：
  名称：

  Arene–Ruthenium(II) Acylpyrazolonato Complexes: Apoptosis-Promoting Effects on Human Cancer Cells

  摘要：

  A series of ruthenium(II) arene complexes with the 4-(biphenyl-4-carbonyl)-3-methyl-1-phenyl-5-pyrazolonate ligand, and related 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives, has been synthesized. The compounds have been characterized by NMR and IR spectroscopy, ESI mass spectrometry, elemental analysis, and X-ray crystallography. Anti-proliferative activity in four human cancer cell lines was determined by MTT assay, yielding dose- and cancer cell line-dependent IC50 values of 9-34 mu M for three hexamethylbenzene-ruthenium complexes, whereas the other metal complexes were much less active. Apoptosis was the mechanism involved in the anticancer activity of such compounds. In fact, the hexamethylbenzene-ruthenium complexes activated caspase activity, with consequent DNA fragmentation, accumulation of pro-apoptotic proteins (p27, p53, p89 PARP fragments), and the concomitant down-regulation of antiapoptotic protein Bcl-2. Biosensor-based binding studies indicated that the ancillary ligands were critical in determining the DNA binding affinities, and competition binding experiments further characterized the nature of the interaction.

  DOI：

  10.1021/jm500458c

文献信息

• Arene–Ruthenium(II) Acylpyrazolonato Complexes: Apoptosis-Promoting Effects on Human Cancer Cells
  作者：Riccardo Pettinari、Claudio Pettinari、Fabio Marchetti、Brian W. Skelton、Allan H. White、Laura Bonfili、Massimiliano Cuccioloni、Matteo Mozzicafreddo、Valentina Cecarini、Mauro Angeletti、Massimo Nabissi、Anna Maria Eleuteri

  DOI：10.1021/jm500458c

  日期：2014.6.12

  A series of ruthenium(II) arene complexes with the 4-(biphenyl-4-carbonyl)-3-methyl-1-phenyl-5-pyrazolonate ligand, and related 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives, has been synthesized. The compounds have been characterized by NMR and IR spectroscopy, ESI mass spectrometry, elemental analysis, and X-ray crystallography. Anti-proliferative activity in four human cancer cell lines was determined by MTT assay, yielding dose- and cancer cell line-dependent IC50 values of 9-34 mu M for three hexamethylbenzene-ruthenium complexes, whereas the other metal complexes were much less active. Apoptosis was the mechanism involved in the anticancer activity of such compounds. In fact, the hexamethylbenzene-ruthenium complexes activated caspase activity, with consequent DNA fragmentation, accumulation of pro-apoptotic proteins (p27, p53, p89 PARP fragments), and the concomitant down-regulation of antiapoptotic protein Bcl-2. Biosensor-based binding studies indicated that the ancillary ligands were critical in determining the DNA binding affinities, and competition binding experiments further characterized the nature of the interaction.
• Ring-opening polymerization of<scp>l</scp>-lactide catalyzed by calcium complexes
  作者：Mon-Wei Hsiao、Chu-Chieh Lin

  DOI：10.1039/c2dt32487c

  日期：——

  A series of calcium complexes supported by NNO-tridentate ketiminate ligands have been synthesized and characterized. X-ray structural studies indicate that these complexes bear a mononuclear feature with hexa-coordinated calcium centers bonding to two ketiminate ligands. Polymerization of L-lactide catalyzed by these complexes proceeds rapidly and well controlled in the presence of a variety of alcohols. In addition, these complexes reveal good catalytic activity even with the addition of up to 80 equiv. of benzyl alcohol as a transfer agent. Furthermore, kinetic studies show ROP of L-lactide is a first-order dependency on [LA] and a second-order dependency on [BnOH].

  我们合成并鉴定了一系列由 NNO-三叉酮亚胺配体支持的钙络合物。X 射线结构研究表明，这些配合物具有单核特征，六配位钙中心与两个酮亚胺配体成键。在这些配合物的催化下，L-内酰胺的聚合反应在多种醇类存在的情况下均能快速进行，且控制良好。此外，即使添加多达 80 等量的苯甲醇作为转移剂，这些复合物也能显示出良好的催化活性。此外，动力学研究表明，L-内酰胺的 ROP 与 [LA] 呈一阶依赖关系，与 [BnOH] 呈二阶依赖关系。