4,5-dihydro-1-phenyl-3-diphenyl-5-(4-methoxyphenyl)-1H-pyrazole | 50497-96-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4,5-dihydro-1-phenyl-3-diphenyl-5-(4-methoxyphenyl)-1H-pyrazole
• 英文别名: 3-biphenyl-4-yl-5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazole；3-Biphenyl-4-yl-5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol；3-(4-Methoxyphenyl)-2-phenyl-5-(4-phenylphenyl)-3,4-dihydropyrazole
• CAS: 50497-96-6
• 化学式: C₂₈H₂₄N₂O
• 分子量: 404.511
• InChiKey: RJZJXVHQVFWREU-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C(Solv: ethanol (64-17-5))
• 沸点：
  573.6±60.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4,5-dihydro-1-phenyl-3-diphenyl-5-(4-methoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  SAR studies of differently functionalized 4′-phenylchalcone based compounds as inhibitors of cathepsins B, H and L

  摘要：

  4'-苯基查尔酮及其环化衍生物作为新型卡他普星B、H和L的抑制剂，具有潜在的抗癌特性。

  DOI：

  10.1039/c5ra00357a

文献信息

• Synthesis and Characterization of 2-Phenylpyrazoline Derivatives and Evaluation of their Activities against Antimicrobial and Breast Cancer Cell Line in vitro and in silico Studies
  作者：RAJA CHINNAMANAYAKAR、M.R. EZHILARASI

  DOI：10.14233/ajchem.2019.21915

  日期：2019.5.25

  The new series of 2-phenylpyrazoline derivatives (2a-j) were synthesized and evaluated for their antimicrobial, in silico and in vitro anticancer activity was performed by MTT assay using MDA-MB-231 (human breast adenocarcinoma) cell line. The 2-phenylpyrazoline derivatives (2a-j) were obtained by the cyclization of chalcones with phenylhydrazine hydrochloride. Synthesized compounds were confirmed using FT-IR, 1H NMR and 13C NMR spectral data. Molecular docking studies were carried out using Auto Dock Tool version 1.5.6 and Auto dock version 4.2.5.1 docking program. in silico Docking study, compound 2d showed good binding score and good binding interaction with selected bacterial proteins and breast cancer protein. Based on this result, compound 2d was performed the anticancer activity by MTT assay method. From this result, compound 2d shown the LC50 value is 185.30 ± 1. 469 μg/mL. From the antibacterial activity compound 2i (2,3-dichloro substituted 2-pyrazoline derivative) showed a good zone of inhibition at high concentration (100 mg/mL) as compared to other derivatives (2a-j) and compound 2c (fluoro substituted 2-phenylpyrazoline derivative) showed a good zone of inhibition at low concentration (25 mg/mL) compared to other derivative (2a-j).

  新系列的2-苯基吡唑啉衍生物（2a-j）被合成并评估其抗菌、体外和体内抗癌活性，通过MTT测定法使用MDA-MB-231（人类乳腺腺癌）细胞系进行了评估。2-苯基吡唑啉衍生物（2a-j）是通过香豆素与盐酸苯基肼的环化得到的。合成的化合物通过FT-IR、1H NMR和13C NMR光谱数据进行了确认。分子对接研究使用Auto Dock工具版本1.5.6和Auto dock版本4.2.5.1对接程序进行。体外对接研究中，化合物2d显示出良好的结合得分和与选定的细菌蛋白和乳腺癌蛋白的良好结合相互作用。基于这个结果，化合物2d通过MTT测定法进行了抗癌活性评估。根据这个结果，化合物2d的LC50值为185.30 ± 1.469 μg/mL。从抗菌活性方面，化合物2i（2,3-二氯取代的2-吡唑啉衍生物）在高浓度（100 mg/mL）下显示出较好的抑菌区域，相比其他衍生物（2a-j），而化合物2c（氟取代的2-苯基吡唑啉衍生物）在低浓度（25 mg/mL）下显示出较好的抑菌区域，相比其他衍生物（2a-j）。
• 1,3,5-Triaryl-2-pyrazolines for Use as Scintillation Solutes
  作者：RICHARD H. WILEY、C. H. JARBOE、F. N. HAYES、E. HANSBURY、J. T. NIELSEN、P. X. CALLAHAN、M. C. SELLARS

  DOI：10.1021/jo01099a025

  日期：1958.5