(E)-1-(4-methylphenyl)-3-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one | 1239732-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1-(4-methylphenyl)-3-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one
• CAS: 1239732-57-0
• 化学式: C₂₅H₁₉N₃O₃
• 分子量: 409.444
• InChiKey: XSHJIGAXLJQZPB-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  78.03
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methylphenyl)-3-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以91%的产率得到3-(4-nitrophenyl)-1-phenyl-4-[3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-yl]-1H-pyrazole
  参考文献：
  名称：

  Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents

  摘要：

  Novel (E)-1-aryl-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones 5/6 (pyrazolic chalcones) were synthesized from a Claisen-Schmidt reaction of 3-aryl-1-phenylpyrazol-4-carboxaldehydes 4 with several acetophenone derivatives 1. Subsequently, the microwave-assisted cyclocondensation reaction of chalcones 5/6 with hydrazine afforded the new racemic 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazoles 7 or their N-acetyl derivatives 8 and 9 when reactions where carried out in DMF or acetic acid, respectively. Several of these compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where 5c and 9g showed remarkable activity mainly against leukemia (K-562 and SR), renal cancer (UO-31) and non-small cell lung cancer (HOP-92) cell lines, with the most important GI(50) values ranging from 0.04 to 11.4 mu M, from the in vitro assays. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.013
• 作为产物：
  描述：

  3-(4-硝基苯基)-1-苯基-1H-吡唑-4-甲醛 、 对甲基苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以89%的产率得到(E)-1-(4-methylphenyl)-3-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents

  摘要：

  Novel (E)-1-aryl-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones 5/6 (pyrazolic chalcones) were synthesized from a Claisen-Schmidt reaction of 3-aryl-1-phenylpyrazol-4-carboxaldehydes 4 with several acetophenone derivatives 1. Subsequently, the microwave-assisted cyclocondensation reaction of chalcones 5/6 with hydrazine afforded the new racemic 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazoles 7 or their N-acetyl derivatives 8 and 9 when reactions where carried out in DMF or acetic acid, respectively. Several of these compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where 5c and 9g showed remarkable activity mainly against leukemia (K-562 and SR), renal cancer (UO-31) and non-small cell lung cancer (HOP-92) cell lines, with the most important GI(50) values ranging from 0.04 to 11.4 mu M, from the in vitro assays. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.013