2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamide | 3985-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamide
• 英文别名: 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide；2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pryazole-4-yl)benzamide；4-(2-chloro-benzoylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one；4-(2-Chlor-benzoylamino)antipyrin；2-chloro-N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)benzamide
• CAS: 3985-30-6
• 化学式: C₁₈H₁₆ClN₃O₂
• mdl: MFCD00382566
• 分子量: 341.797
• InChiKey: RUQUWLFFIMYLPY-UHFFFAOYSA-N

物化性质

• 熔点：
  261-262 °C
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯苯甲酸 在 吡啶 、 氯化亚砜 作用下， 反应 5.0h， 生成 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamide
  参考文献：
  名称：

  Synthesis, characterization and biological evaluation of N-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)benzamides

  摘要：

  将模型化的h-GCAP的活性位点残基与模板h-PLAP进行比较。

  DOI：

  10.1039/c5ra17568b

文献信息

• Intermolecular interactions in antipyrine-like derivatives 2-halo-<i>N</i>-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1<i>H</i>-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
  作者：Aamer Saeed、Asma Khurshid、Ulrich Flörke、Gustavo A. Echeverría、Oscar E. Piro、Diego M. Gil、Mariana Rocha、Antonio Frontera、Hesham R. El-Seedi、Amara Mumtaz、Mauricio F. Erben

  DOI：10.1039/d0nj03958f

  日期：——

  contacts were observed. Their solid-state structures have been analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and the stabilization is dominated via the electrostatic energy contribution. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP), and a combination

  本文报道了两种新的安替比林衍生物的合成，X射线结构表征，Hirshfeld表面分析和DFT计算。特别是2-溴-N-（2,3-二氢-1,5-二甲基-3-氧代-2-苯基-1 H-吡唑-4-基）苯甲酰胺（1）和2-氯-N-（ 2，3-二氢-1，5-二甲基-3-氧代-2-苯基-1 H-吡唑-4-基）苯甲酰胺（2）以高收率合成并通过光谱表征。两种化合物都是同构的，并且在单斜晶P 2 1 / c中结晶空间群。两种化合物的晶体堆积主要通过N–H⋯O和C–H⋯O氢键的结合来稳定。此外，观察到C–H⋯π和孤对⋯π接触。已通过Hirshfeld表面分析对它们的固态结构进行了分析，包括对不同能量构架的评估，表明分子片主要由氢键形成，并且稳定作用主要由静电能贡献。这些研究得到了DFT计算（B3LYP-D3 / def2-TZVP）的补充，并且结合了QTAIM / NCIplot分析，揭示了H键相互作用与能量相关（范围从0
• 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.
• 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。