3-anthracen-9-yl-5-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole | 1290176-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-anthracen-9-yl-5-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole
• 英文别名: 3-anthracen-9-yl-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole
• CAS: 1290176-37-2
• 化学式: C₂₃H₁₇N₃O₂
• 分子量: 367.407
• InChiKey: GQZDURBFXSVNIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-anthracen-9-yl-5-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole 、 苯甲酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以91%的产率得到(3-(anthracen-10-yl)-4,5-dihydro-5-(4-nitrophenyl)-pyrazol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Efficient Synthesis and Characterization of Anthracene based 1,3,5-Trisubstituted Pyrazoline Derivatives

  摘要：

  一系列含有1,3,5-三取代吡唑啉衍生物（3a-p）的蒽醌骨架新化合物被合成，并通过1H NMR，13C NMR，FTIR，质谱和元素分析方法进行了良好的表征。反应是从蒽醌基吡唑啉（1a-p）和苯甲酰氯（2）在无水K2CO3存在下，在丙酮中回流反应2-7小时完成的。获得的产率为良好至优异（80-94％）。

  DOI：

  10.14233/ajchem.2021.23038
• 作为产物：
  描述：

  1-(对硝基苯基)-3-(9-蒽基)-2-丙烯-1-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 以76%的产率得到3-anthracen-9-yl-5-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation

  摘要：

  In an effort to develop selective MAO (monoamine oxidase) B inhibitors, structure based virtual screening was initiated on an in-house library. Top 10 HITS were synthesized and evaluated for MAO (A and B) inhibitory activity, both against human and rat enzymes. All the compounds were found selective, reversible and active in nM range (100 times more potent than selegeline) towards MAO-B. Outstanding co-relation between predicted and experimental K(i) values were observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.030

文献信息

• Et ₃ N‐Prompted Efficient Synthesis of Anthracenyl Pyrazolines and Their Cytotoxicity Evaluation against Cancer Cell Lines
  作者：Thechano Merry、Prabhakar Maddela、Kiran Devaraya、Anand K. Kondapi、Chullikkattil P. Pradeep

  DOI：10.1002/jhet.3636

  日期：2019.9

  compounds 3a, 3j, 3l, 3m, 3n, and 3o showed a highly potential activity against HeLa cells (IC50: 0.22, 0.3, 0.3, 0.10, 0.25, and 0.25 μM), while compounds 3i, 3k, 3l, and 3m showed a significant cytotoxic activity in HepG2 cells (IC50: 0.22, 0.44, 0.40, and 0.22 μM), whereas compounds 3a, 3b, 3d, and 3e exhibit a promising cytotoxicity against MCF‐7 cells (IC50: 0.73, 0.495, 0.493, and 0.66 μM).

  合成了一系列蒽基吡唑啉衍生物（3a - o），目的是评估其体外抗癌活性。蒽基吡唑啉化合物是通过各种蒽基查耳酮（1a – o）和水合肼（2）之间的反应制备的。该反应在三乙胺和乙醇的存在下在回流条件下进行24小时，所得收率从良好到优异（90-97％）。每种化合物的结构均可通过IR，1 H-NMR，13 C-NMR，元素分析和质谱技术很好地表征，以及化合物3d和3d的分子结构。3e通过单晶X射线晶体学方法解决。评估了新合成的化合物（3a - o）对四种人类癌细胞系MCF-7（乳腺癌细胞系），SK-N-SH（神经母细胞瘤癌细胞系），HeLa（宫颈癌细胞）的体外细胞毒性研究品系和HepG2（肝癌细胞系），筛选结果显示，除SK‐N‐SH细胞外，大多数合成化合物对这三种细胞系均具有很强的细胞毒性作用。值得注意的是，化合物3a，3j，3l，3m，3n和3o对HeLa细胞（IC50：0.22，0.3，0.3，0
• Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation
  作者：Nibha Mishra、D. Sasmal

  DOI：10.1016/j.bmcl.2011.02.030

  日期：2011.4

  In an effort to develop selective MAO (monoamine oxidase) B inhibitors, structure based virtual screening was initiated on an in-house library. Top 10 HITS were synthesized and evaluated for MAO (A and B) inhibitory activity, both against human and rat enzymes. All the compounds were found selective, reversible and active in nM range (100 times more potent than selegeline) towards MAO-B. Outstanding co-relation between predicted and experimental K(i) values were observed. (C) 2011 Elsevier Ltd. All rights reserved.
• Efficient Synthesis and Characterization of Anthracene based 1,3,5-Trisubstituted Pyrazoline Derivatives
  作者：Thechano Merry、Prabhakar Maddela

  DOI：10.14233/ajchem.2021.23038

  日期：——

  A new series of anthracene scaffold containing 1,3,5-trisubstituted pyrazoline derivatives (3a-p) were synthesized and well characterized by 1H NMR, 13C NMR, FTIR, mass spectroscopic and elemental analysis methods. The reactions were carried out from anthracenyl pyrazolines (1a-p) and benzoyl chloride (2) in presence of anhydrous K2CO3 in acetone under reflux conditions for 2-7 h. The obtained yields were good to excellent (80-94%).

  一系列含有1,3,5-三取代吡唑啉衍生物（3a-p）的蒽醌骨架新化合物被合成，并通过1H NMR，13C NMR，FTIR，质谱和元素分析方法进行了良好的表征。反应是从蒽醌基吡唑啉（1a-p）和苯甲酰氯（2）在无水K2CO3存在下，在丙酮中回流反应2-7小时完成的。获得的产率为良好至优异（80-94％）。