ethyl 1-(4-(2-(2-(nitrooxy)acetyl)hydrazinecarbonyl)phenyl)-5-(4-chlorophenyl)-3-oxo-2,3-dihydropyrazole-4-carboxylate | 1198211-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-(2-(2-(nitrooxy)acetyl)hydrazinecarbonyl)phenyl)-5-(4-chlorophenyl)-3-oxo-2,3-dihydropyrazole-4-carboxylate
• 英文别名: ethyl 3-(4-chlorophenyl)-2-[4-[[(2-nitrooxyacetyl)amino]carbamoyl]phenyl]-5-oxo-1H-pyrazole-4-carboxylate
• CAS: 1198211-05-0
• 化学式: C₂₁H₁₈ClN₅O₈
• 分子量: 503.856
• InChiKey: WKABMRIWMNNBRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  172
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ethyl 1-(4-(2-(2-chloroacetyl)hydrazinecarbonyl)phenyl)-5-(4-chlorophenyl)-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以65%的产率得到ethyl 1-(4-(2-(2-(nitrooxy)acetyl)hydrazinecarbonyl)phenyl)-5-(4-chlorophenyl)-3-oxo-2,3-dihydropyrazole-4-carboxylate
  参考文献：
  名称：

  Design, synthesis and pharmacological screening of novel nitric oxide donors containing 1,5-diarylpyrazolin-3-one as nontoxic NSAIDs

  摘要：

  Various substituted 1,5-diarylpyrazol-3-one derivatives were synthesized and screened for analgesic, anti-inflammatory activities, ulcerogenic potential and for their ability to release nitric oxide. Most compounds exhibited significant analgesic and anti-inflammatory activities. It was interesting to note that out of ten compounds, 7j (59.64%) was found to have anti-inflammatory activity greater than the standard drug Indomethacin (57.89%), whereas compound 7b (57.89%) was found to be equipotent to that of standard, Indomethacin. The pharmacological studies suggested that the presence of 4-nitro and 2-methoxy on phenyl ring at C-5 of pyrazole has a significant anti-inflammatory activity and 4-chloro substitution on same phenyl ring was found to have decreased activity. However only a phenyl substituted derivative was found to have most potent activity. Compound 7j containing plane phenyl at C5 of pyrazole was found to have significant analgesic activity (56.86%) in acetic acid induced writhing model. Compounds 7d and 7i having 4-chloro substituted phenyl ring showed least analgesic activity (10.78%) and (6.86%) respectively. The compounds also showed significantly reduced GI-ulcerogenicity and gastroprotective results in histopathological studies i.e. they were found to be causing no mucosal injury. All the synthesized compounds were found to exhibit significant nitric oxide releasing activity, in both in vitro and in vivo models. Molecular docking studies served to be an important tool for the study of binding of compounds with that of a COX-2 enzyme. The results of the docking studies were found to endorse the result of experimental work. Thus, the rationale used to design the NCEs was found to produce the promising results as anticipated. Therefore it can be said that the strategy employed can serve as an important tool in future for the design and development of novel therapeutic agents of various categories too. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.035