3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbonitrile | 1369695-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbonitrile
• CAS: 1369695-26-0
• 化学式: C₂₁H₂₀ClN₃
• 分子量: 349.863
• InChiKey: NCOXZSQCAVSADD-UHFFFAOYSA-N

物化性质

• 沸点：
  512.5±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  41.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbonitrile 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以74%的产率得到3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-N-hydroxy-1H-pyrazole-5-carboximidamide
  参考文献：
  名称：

  Synthesis and biological validation of novel pyrazole derivatives with anticancer activity guided by 3D-QSAR analysis

  摘要：

  Using literature data on anticancer activity of pyrazole derivatives, 3D-QSAR models were developed and 3D-QSAR analysis was performed. The 3D-QSAR analysis enabled identification of molecular properties that have the highest impact on antitumor activity against lung cancer cells. The results of 3D-QSAR analysis were taken into account while new compounds were designed. Obtained 3D-QSAR models were used for prediction of activity of new compounds. In this way, design of new compounds was guided by 3D-QSAR analysis which was performed on literature data. Ten new pyrazole derivatives were synthesised and their antitumor activities against A549 and NCIH23 lung cancer cells were validated. In order to obtain full profile of anticancer activity, cells viability (MTS) assays were combined with cell proliferation (BrdU) assays which measure actively dividing cells in treated sample. Experimental measurements showed good agreement between predicted and measured activities for majority of compounds. Also, anticancer activities of new pyrazole derivatives pointed to the chemical groups that can be useful in designing antitumor molecules. Substitution of hydrazine linker with rigid, 1,2,4-oxadiazole moiety resulted in compound 10, which has low (if any) cytotoxic activity and high potential cytostatic activity. Therefore, compound 10 presents a good starting point for design of new, more potent and safer anticancer therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.032
• 作为产物：
  描述：

  3-(4-chlorophenyl)-1-([6-(1,1-dimethylethyl)-3-pyridinyl]methyl)-1H-pyrazole-5-carboxamide 在 吡啶 、 三氯氧磷 作用下， 反应 2.0h， 以89%的产率得到3-(4-chlorophenyl)-1-([4-(1,1-dimethylethyl)phenyl]methyl)-1H-pyrazole-5-carbonitrile
  参考文献：
  名称：

  Synthesis and biological validation of novel pyrazole derivatives with anticancer activity guided by 3D-QSAR analysis

  摘要：

  Using literature data on anticancer activity of pyrazole derivatives, 3D-QSAR models were developed and 3D-QSAR analysis was performed. The 3D-QSAR analysis enabled identification of molecular properties that have the highest impact on antitumor activity against lung cancer cells. The results of 3D-QSAR analysis were taken into account while new compounds were designed. Obtained 3D-QSAR models were used for prediction of activity of new compounds. In this way, design of new compounds was guided by 3D-QSAR analysis which was performed on literature data. Ten new pyrazole derivatives were synthesised and their antitumor activities against A549 and NCIH23 lung cancer cells were validated. In order to obtain full profile of anticancer activity, cells viability (MTS) assays were combined with cell proliferation (BrdU) assays which measure actively dividing cells in treated sample. Experimental measurements showed good agreement between predicted and measured activities for majority of compounds. Also, anticancer activities of new pyrazole derivatives pointed to the chemical groups that can be useful in designing antitumor molecules. Substitution of hydrazine linker with rigid, 1,2,4-oxadiazole moiety resulted in compound 10, which has low (if any) cytotoxic activity and high potential cytostatic activity. Therefore, compound 10 presents a good starting point for design of new, more potent and safer anticancer therapeutics. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.032