N'-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)benzohydrazide | 305865-25-2

• 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'-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)benzohydrazide
• 英文别名: N-[(5-chloro-3-methyl-1-phenylpyrazol-4-yl)methylideneamino]benzamide
• CAS: 305865-25-2
• 化学式: C₁₈H₁₅ClN₄O
• mdl: MFCD00385901
• 分子量: 338.796
• InChiKey: HOOPMOKMRLIDDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酸乙酯 在 胍基乙酸 、 一水合肼 作用下， 生成 N'-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)benzohydrazide
  参考文献：
  名称：

  Pharmacological screening for anti-inflammatory, analgesic activity of pyrazolyl derivatives along with molecular docking studies

  摘要：

  The pyrazole derivatives were synthesized and pharmacologically evaluated for analgesic (tail flick) and anti-inflammatory (based on carrageenan-induced paw edema) activities. Compound 4k showed high potency as an anti-inflammatory agent after 3 and 4-h time intervals (P < 0.001) equipotent to indomethacin. They were devoid of ulcerogenic potential when administered at a dose of 30 mg/kg. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the byproduct of lipid peroxidation. Further docking studies of titled compounds was done to understand key interactions responsible for observed inhibition of COX enzyme. The most active compound 4k was found to have -11.192 kcal/mol, as the free energy of binding. Various other key interactions between the synthesized molecules and active site of COX-2 enzyme, responsible for the obtained pharmacological results were also reported. Most of the active compounds were docked well into the active sites of the receptor.

  DOI：

  10.1007/s00044-011-9901-0

文献信息

• New Hydrazone Derivatives of Pyrazole-4-carboxaldehydes Exhibited Anti-inflammatory Properties
  作者：Mingxia Song、Bing Liu、Shengwang Yu、Shihui He、Yuqiu Liang、Sifan Li、Qiuyan Chen、Xianqing Deng

  DOI：10.2174/1570180816666190731113441

  日期：2020.4.25

  Background: Several series of hydrazone derivatives of pyrazole-4-carboxaldehydes (4- 11) were designed and synthesized to screen their inflammatory activity. Methods: The products were characterized by 1H NMR, 13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their antiinflammatory activity. Results and Conclusion: Bioassays indicated

  背景：设计并合成了几系列的吡唑-4-甲醛（4- 4-11）衍生物，以筛选其炎症活性。 方法：用1 H NMR，13 C NMR和HRMS对产物进行表征。用体外LPS诱导的TNF-α模型和体内二甲苯诱导的耳水肿模型评估其抗炎活性。 结果与结论：生物测定表明，大多数化合物在10 µg / mL的浓度下均能显着抑制TNF-α的表达。化合物7b和11c是两种最有效的化合物，以剂量依赖性方式表现出TNF-α抑制能力，IC50值分别为5.56和3.69 µM。在体内，腹膜内给药7b和11c在剂量为20和50 mg / kg时可明显抑制耳水肿。化合物11c在20 mg / kg的剂量下抑制水肿49.59％，与在相同剂量下的参考药物地塞米松相当（抑制50.49％）。为了解结合模式，进行了代表分子7b和11c的分子对接，这表明这两种化合物均与TNF-α具有强力结合，