5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester | 1186210-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester
• CAS: 1186210-21-8
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: KHYNKAYMKQXHIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.35
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 54.67h， 生成 5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of pyrazole-based 1,5-diaryl compounds as potent anti-inflammatory agents

  摘要：

  Series of 1,5-diaryl pyrazole ester derivatives have been synthesized and found to contain potent inhibitory activity against cyclooxygenase-2 (COX-2) enzyme. The article describes synthesis of the target pyrazole analogs and biological assay using Carrageenan induced rat paw for investigation.

  DOI：

  10.1007/s00044-011-9774-2
• 作为产物：
  描述：

  甲醇 、 4-(bis(methylsulfanyl)methylene)-5-methyl-2-phenyl-2,4-dihydropyrazol-3-one 在 sodium ethanolate 作用下， 以80%的产率得到5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; Design, Synthesis, Docking and in Vivo Activity

  摘要：

  我们合成了一系列吡唑酯原药类似物，发现它们含有对环氧合酶-2（COX-2）酶的强效抑制剂。本文介绍了目标吡唑类似物的合成。通过 1H-、13C-NMR 质谱（MS）确认了合成的互酯原药（6-8c）的结构，并通过 TLC 和元素分析确定了其纯度。在实验模型（角叉菜胶诱发的水肿）中对这些化合物进行的体内生物学评估证明了它们具有抗炎活性。通过对 COX-2 催化位点的对接研究，确定了潜在的抗炎先导化合物。最终选择了一种具有良好结合能的先导衍生物。

  DOI：

  10.1248/cpb.58.634

文献信息

• Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents
  作者：Ashish Kumar Tewari、Ved Prakash Singh、Pratima Yadav、Garima Gupta、Amit Singh、Raj Kumar Goel、Pravin Shinde、C. Gopi Mohan

  DOI：10.1016/j.bioorg.2014.05.004

  日期：2014.10

  A novel series of pyrazole derivatives were synthesized and evaluated in vivo for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Among all compounds, 5a, and 5b showed comparable anti-inflammatory activity to Nimesulide, the standard drug taken for the studies. In silico (docking) studies were carried out to investigate the theoretical binding mode of the compounds to target the cyclooxygenase (COX-2) using Autodock 4.2.
• Applications of Dithioacetals in Ester Synthesis
  作者：Ashish Kumar Tewari、Priyanka Srivastava

  DOI：10.1080/00397910802654641

  日期：2009.7.21

  The -oxoketene dithioacetals are simple synthetic intermediates widely utilized and implicated for the synthesis of a variety of heterocyclic compounds other than alicyclic and aromatic compounds. They act as 1,3-electrophilic three-carbon synthons. The -oxoketene dithioacetal of pyrazolone derivatives can be efficiently converted through a base-catalyzed alcoholysis into the corresponding ester in a single one-step reaction with good yield of pure products. In this article, we summarize recent direct conversion of -oxoketene dithioacetals to highly desirable esters. The overall process is an example of intramolecular rearrangement of bonds. Characterization and identification of all synthesized compounds were assigned through 1H NMR and mass spectroscopy.
• Condensed phase conformational isomerization of 5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propoxy]-3-methyl-1H-pyrazole-4-carboxylic acid methyl ester
  作者：Ashish Kumar Tewari、Priyanka Srivastave、Ved Prakash Singh、Carmen Puerta、Pedro Valerga

  DOI：10.3998/ark.5550190.0011.911

  日期：——

  Presence of ester group adjacent to methyl group in a pyrazole ring system results in a flexible hydrogen bond. This bond can be freely rotate to generate the conformational isomers. Conformational isomers can be separated if the barrier to rotation or the energy difference between the two configurations is large. In the present study, in solution state, this spinning is so fast that it was difficult to predict the conformational change whereas the condensation of molecules in solid state, existence of two conformations have been predicted.