1-(4-chlorophenyl)-4,4,4-trifluoro-2-(2-(4-methoxyphenyl)hydrazono)butane-1,3-dione | 893691-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-4,4,4-trifluoro-2-(2-(4-methoxyphenyl)hydrazono)butane-1,3-dione
• 英文别名: 1-(4-chlorophenyl)-2-(2-(4-methoxyphenyl)hydrazono)-4,4,4-trifluorobutane-1,3-dione；1-(4-chlorophenyl)-4,4,4-trifluoro-2-[(4-methoxyphenyl)hydrazinylidene]butane-1,3-dione
• CAS: 893691-68-4
• 化学式: C₁₇H₁₂ClF₃N₂O₃
• 分子量: 384.742
• InChiKey: NSOPECLWMQEDGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-4,4,4-trifluoro-2-(2-(4-methoxyphenyl)hydrazono)butane-1,3-dione 在 肼 作用下， 以 乙醇 为溶剂， 生成 3-(4-chlorophenyl)-4-(2-(4-methoxyphenyl)hydrazono)-5-trifluoromethyl-4H-pyrazole
  参考文献：
  名称：

  Antitumor evaluation and molecular docking study of substituted 2-benzylidenebutane-1,3-dione, 2-hydrazonobutane-1,3-dione and trifluoromethyl-1H-pyrazole analogues

  摘要：

  A series of 2-(arylidene)-1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-diones (2-4), 4-(arylidene)-3-(4-chlorophenyl)-5-(trifluoromethyl)-4H-pyrazoles (5-7), 1-(4-chlorophenyl)-4,4,4-trifluoro-2-( 2-(aryl) hydrazono) butane-1,3-diones (8, 9), 3-(4-chlorophenyl)-4-(2-(aryl) hydrazono)-5-(trifluoromethyl)-4H-pyrazoles (10, 11), 2-((3-(4-chlorophenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazol4-yl) methylene) malononitrile (13), 2-((5-(4-chlorophenyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl) methylene) cycloalkan-1-ones (14, 15) and 1-(aryl)-3-(5-(4-chlorophenyl)-1-phenyl-3-( trifluoromethyl)-1H-pyrazol-4-yl) prop-2-en-1-ones (16, 17) were designed, synthesized and evaluated for their in vitro antitumor activity. 1-(4-Chlorophenyl)-4,4,4-trifluoro-2-(2-(4-methoxyphenyl) hydrazono) butane-1,3-dione (8) showed potential and broad spectrum antitumor activity compared to the known drug 5-FU with GI(50,) (6.61 and 22.60 mu M), TGI (42.66 and <100 mu M) and LC50 (93.33 and <100 mu M) values, respectively. On the other hand, compound 8 yielded selective activities toward melanoma, colon, non-small lung and breast cancer cell lines compared with erlotinib and gefitinib. Molecular docking methodology was performed for compound 8 into binding site of B-RAFV600E and EGFR kinases which showed similar binding mode to vemurafenib (PLX4032) and erlotinib, respectively.

  DOI：

  10.3109/14756366.2014.960863
• 作为产物：
  描述：

  对氯苯乙酮 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.42h， 生成 1-(4-chlorophenyl)-4,4,4-trifluoro-2-(2-(4-methoxyphenyl)hydrazono)butane-1,3-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: Molecular docking study

  摘要：

  New arylhydrazone derivatives and a series of 1,5-diphenyl pyrazoles were designed and synthesized from 1-(4-chlorophenyl)-4,4,4-trifuorobutane-1,3-dione 1. The newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw oedema model. Moreover, they were tested for their inhibitory activity against ovine COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Some of the new compounds (2f, 6a and 6d) showed a reasonable in vitro COX-2 inhibitory activity, with IC50 value of 0.45 mu M and selectivity index of 111.1. A virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Docking study of the synthesized compounds 2f, 6a and 6d into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.027

文献信息

• Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: Molecular docking study
  作者：Magda A.-A. El-Sayed、Naglaa I. Abdel-Aziz、Alaa A.-M. Abdel-Aziz、Adel S. El-Azab、Yousif A. Asiri、Kamal E.H. ElTahir

  DOI：10.1016/j.bmc.2011.04.027

  日期：2011.6

  New arylhydrazone derivatives and a series of 1,5-diphenyl pyrazoles were designed and synthesized from 1-(4-chlorophenyl)-4,4,4-trifuorobutane-1,3-dione 1. The newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw oedema model. Moreover, they were tested for their inhibitory activity against ovine COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Some of the new compounds (2f, 6a and 6d) showed a reasonable in vitro COX-2 inhibitory activity, with IC50 value of 0.45 mu M and selectivity index of 111.1. A virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Docking study of the synthesized compounds 2f, 6a and 6d into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.
• Antitumor evaluation and molecular docking study of substituted 2-benzylidenebutane-1,3-dione, 2-hydrazonobutane-1,3-dione and trifluoromethyl-1H-pyrazole analogues
  作者：Ibrahim A. Al-Suwaidan、Naglaa I. Abdel-Aziz、Adel S. El-Azab、Magda A.-A. El-Sayed、Amer M. Alanazi、Mahmoud B. El-Ashmawy、Alaa A.-M. Abdel-Aziz

  DOI：10.3109/14756366.2014.960863

  日期：2015.7.4

  A series of 2-(arylidene)-1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-diones (2-4), 4-(arylidene)-3-(4-chlorophenyl)-5-(trifluoromethyl)-4H-pyrazoles (5-7), 1-(4-chlorophenyl)-4,4,4-trifluoro-2-( 2-(aryl) hydrazono) butane-1,3-diones (8, 9), 3-(4-chlorophenyl)-4-(2-(aryl) hydrazono)-5-(trifluoromethyl)-4H-pyrazoles (10, 11), 2-((3-(4-chlorophenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazol4-yl) methylene) malononitrile (13), 2-((5-(4-chlorophenyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl) methylene) cycloalkan-1-ones (14, 15) and 1-(aryl)-3-(5-(4-chlorophenyl)-1-phenyl-3-( trifluoromethyl)-1H-pyrazol-4-yl) prop-2-en-1-ones (16, 17) were designed, synthesized and evaluated for their in vitro antitumor activity. 1-(4-Chlorophenyl)-4,4,4-trifluoro-2-(2-(4-methoxyphenyl) hydrazono) butane-1,3-dione (8) showed potential and broad spectrum antitumor activity compared to the known drug 5-FU with GI(50,) (6.61 and 22.60 mu M), TGI (42.66 and <100 mu M) and LC50 (93.33 and <100 mu M) values, respectively. On the other hand, compound 8 yielded selective activities toward melanoma, colon, non-small lung and breast cancer cell lines compared with erlotinib and gefitinib. Molecular docking methodology was performed for compound 8 into binding site of B-RAFV600E and EGFR kinases which showed similar binding mode to vemurafenib (PLX4032) and erlotinib, respectively.