5-[2-(3-cyano-4,6-dimethylpyridin-2-yloxy)ethoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester | 1248591-80-1

• 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-[2-(3-cyano-4,6-dimethylpyridin-2-yloxy)ethoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester
• 英文别名: Methyl 5-[2-(3-cyano-4,6-dimethylpyridin-2-yl)oxyethoxy]-3-methyl-1-phenylpyrazole-4-carboxylate
• CAS: 1248591-80-1
• 化学式: C₂₂H₂₂N₄O₄
• 分子量: 406.441
• InChiKey: MGFRSIUMUDJPGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(2-bromoethoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester 、 3-氰基-4,6-二甲基-2-羟基吡啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-[2-(3-cyano-4,6-dimethylpyridin-2-yloxy)ethoxy]-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Selective induced polarization through electron transfer in acetone and pyrazole ester derivatives via C–H⋯OC interaction

  摘要：

  一组有机化合物（吡唑酯衍生物，即5-[3-(取代基)-丙氧基]-3-甲基-1-苯基-1H-吡唑-4-羧酸甲酯和5-[2-(取代基)-乙氧基]-3-甲基-1-苯基-1H-吡唑-4-羧酸甲酯）被合成，并通过核磁共振测试它们与丙酮分子的亲和力和稳定性。

  DOI：

  10.1039/c4nj00679h

文献信息

• Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; Design, Synthesis, Docking and in Vivo Activity
  作者：Ashish Kumar Tewari、Priyanka Srivastava、Ved Prakash Singh、Amit Singh、Raj Kumar Goel、Chethampadi Gopi Mohan

  DOI：10.1248/cpb.58.634

  日期：——

  Series of pyrazole ester prodrugs analogues have been synthesized and found to contain highly potent inhibitors of the cyclooxygenase-2 (COX-2) enzyme. The paper describes synthesis of the target pyrazole analogues. The structure of the synthesized mutual ester prodrugs (6—8c) were confirmed by 1H-, 13C-NMR mass spectroscopy (MS) and their purity were ascertained by TLC and elemental analyses. The biological in vivo evaluation of these compounds in experimental models (carrageenan-induced oedema) proved the presence of anti-inflammatory activity. Docking studies into the catalytic site of COX-2 were used to identify potential anti-inflammatory lead compounds. One lead derivative was chosen endowed with good binding energies.

  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。