N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide | 67019-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide
• 英文别名: N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-2-methylbenzamide
• CAS: 67019-60-7
• 化学式: C₁₉H₁₉N₃O₂
• 分子量: 321.379
• InChiKey: XWHLQPMIOKGGKV-UHFFFAOYSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-methylbenzamide 在 盐酸 作用下， 以 水 为溶剂， 反应 48.0h， 以92%的产率得到对甲苯甲酸
  参考文献：
  名称：

  Ru催化的带有新型4-氨基安替比林作为导向基团的苯甲酰胺的C(sp2)-H键芳基化

  摘要：

  报道了一种基于可商购的 4-氨基安替比林 (AAP)的基于设计的新型可移除N , O -双齿导向基团。带有 AAP 导向基团的芳香族苯甲酰胺在温和的反应条件下并使用 [RuCl 2 (PPh 3 ) 3 ] 作为催化剂进行有效的 Ru 催化的 C(sp 2 )-H 键芳基化反应。各种不同取代和电子学上不同的反吡喃基 (AP) 苯甲酰胺参与了 Ru 催化的 C(sp 2 )-H 芳基化反应，并具有良好的产率和良好的官能团耐受性。

  DOI：

  10.1002/ejoc.202100513
• 作为产物：
  描述：

  4-氨基安替比林 以65%的产率得到
  参考文献：
  名称：

  STEPNOVA G. M.; SHMIDT E. V.; ERMOLAEVA L. P.; GRIGOREVSKAYA N. S., IZV. TOMSK. POLITEXN. IN-TA, 1977, 214, 48-50

  摘要：

  DOI：

文献信息

• Synthesis, characterization and biological evaluation of N-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)benzamides
  作者：Aamer Saeed、Syeda Abida Ejaz、Asma Khurshid、Sidra Hassan、Mariya al-Rashida、Muhammad Latif、Joanna Lecka、Jean Sévigny、Jamshed Iqbal

  DOI：10.1039/c5ra17568b

  日期：——

  Comparison of active site residues of modelled h-GCAP with template h-PLAP.

  将模型化的h-GCAP的活性位点残基与模板h-PLAP进行比较。
• Detailed investigation of anticancer activity of sulfamoyl benz(sulfon)amides and 1H–pyrazol–4–yl benzamides: An experimental and computational study
  作者：Jamshed Iqbal、Syeda Abida Ejaz、Aamer Saeed、Mariya al-Rashida

  DOI：10.1016/j.ejphar.2018.05.011

  日期：2018.8

  Cancer is the second leading cause of mortality worldwide. Therapeutic approach to cancer is a multi-faceted one, whereby many cellular/enzymatic pathways have been discovered as important drug targets for the treatment of cancer. A major disadvantage of most of the currently available anticancer drugs is their non-selective cytotoxicity towards cancerous as well as healthy cells. Another major hurdle in cancer therapy is the development of resistance to anticancer drugs. This necessitates the discovery of new molecules with potent and selective cytotoxic activity towards only cancerous cells, with minimum or no damage to the normal/healthy cells. Herein we report detailed investigation into the anticancer activity of sulfamoyl benz(sulfon)amides (1a-1g, 2a-2k) and 1H-pyrazol-4-yl benzamides (3a-3j) against three cancer cell lines, breast cancer cells (MCF-7), bone-marrow cancer cells (K-562) and cervical cancer cells (HeLa). For comparison, screening against healthy baby hamster kidney cells (BHK-21) was carried out. All compounds exhibited selective cytotoxicity towards cancerous cells. Cell cycle analysis was carried out using flow cytometry, followed by fluorescence microscopic analysis. DNA interaction and docking studies were also carried out.