5-methoxy-1-(4-nitrophenyl)-3-trifluoromethyl-1H-pyrazole | 245748-33-8

• 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-methoxy-1-(4-nitrophenyl)-3-trifluoromethyl-1H-pyrazole
• 英文别名: methyl 1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl ether；5-Methoxy-1-(4-nitrophenyl)-3-(trifluoromethyl)pyrazole
• CAS: 245748-33-8
• 化学式: C₁₁H₈F₃N₃O₃
• 分子量: 287.198
• InChiKey: CKVJDHYQPAPEHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-(4-nitrophenyl)-3-trifluoromethyl-1H-pyrazole 在 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 生成 4-(5-Methoxy-3-(trifluoromethyl)-1H-pyrazol-1-yl)aniline
  参考文献：
  名称：

  3,5-Bis(trifluoromethyl)pyrazoles:  A Novel Class of NFAT Transcription Factor Regulator

  摘要：

  A series of bis(trifluoromethyl)pyrazoles (BTPs) has been found to be a novel inhibitor of cytokine production. Identified initially as inhibitors of IL-2 synthesis, the BTPs have been optimized in this regard and even inhibit IL-2 production with a 10-fold enhancement over cyclosporine in an ex vivo assay. Additionally, the BTPs show inhibition of IL-4, IL-5, IL-8, and eotaxin production. Unlike the IL-2 inhibitors, cycloseorine and FK506, the BTPs do not directly inhibit the dephosphorylation of NFAT by calcineurin.

  DOI：

  10.1021/jm990615a
• 作为产物：
  描述：

  4-硝基苯肼 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 5-methoxy-1-(4-nitrophenyl)-3-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  3,5-Bis(trifluoromethyl)pyrazoles:  A Novel Class of NFAT Transcription Factor Regulator

  摘要：

  A series of bis(trifluoromethyl)pyrazoles (BTPs) has been found to be a novel inhibitor of cytokine production. Identified initially as inhibitors of IL-2 synthesis, the BTPs have been optimized in this regard and even inhibit IL-2 production with a 10-fold enhancement over cyclosporine in an ex vivo assay. Additionally, the BTPs show inhibition of IL-4, IL-5, IL-8, and eotaxin production. Unlike the IL-2 inhibitors, cycloseorine and FK506, the BTPs do not directly inhibit the dephosphorylation of NFAT by calcineurin.

  DOI：

  10.1021/jm990615a

文献信息

• AZOLE INHIBITORS OF CYTOKINE PRODUCTION
  申请人：——

  公开号：US20010044445A1

  公开（公告）日：2001-11-22

  Compounds having the formula 1 are useful for treating diseases that are prevented by or ameliorated with Interleukin-2, Interleukin-4, or Interleukin-5 production inhibitors.

  具有以下化学式的化合物对于治疗由白细胞介素-2、白细胞介素-4或白细胞介素-5产生抑制剂预防或改善的疾病是有用的。
• Synthesis and Biological Evaluation of Polyfluoroalkylated Antipyrines and their Isomeric O-Methylpyrazoles
  作者：Natalya Agafonova、Evgeny Shchegolkov、Yanina Burgart、Victor Saloutin、Alexandra Trefilova、Galina Triandafilova、Sergey Solodnikov、Vera Maslova、Olga Krasnykh、Sophia Borisevich、Sergey Khursan

  DOI：10.2174/1573406414666181106145435

  日期：2019.7.2

  O-methylated derivatives resembling celecoxib structure and evaluate biological activities of obtained compounds. Methods: In vitro (permeability) and in vivo (anti-inflammatory and analgesic activities, acute toxicity, hyperalgesia, antipyretic activity, “open field” test) experiments. To suggest the mechanism of biological activity, molecular docking of the synthesized compounds was carried out into the

  背景：正式属于非甾体类抗炎药类的吡唑啉酮长期以来一直用于医疗实践。 目的：我们的目标是合成N-甲基化的1-芳基-3-多氟烷基吡唑并酮类化合物作为安替比林的氟化类似物，它们的异构体类似于塞来昔布的O-甲基化衍生物，并评估所得化合物的生物活性。 方法：体外（通透性）和体内（抗炎和镇痛活性，急性毒性，痛觉过敏，解热活性，“开放视野”试验）实验。为了表明生物学活性的机理，将合成化合物的分子对接进行到COX-1 / 2的酪氨酸位点。 结果：我们开发了一种方便的方法，用于1-芳基-3-多氟烷基吡唑-5-醇的区域选择性甲基化，从而分别合成了N-甲基吡唑酮和O-甲基吡唑，分别作为安替比林和塞来昔布类似物。首次在体外和体内研究了新衍生物的生物学特性。 结论：三氟甲基安替比林代表了用于发现具有抗炎特性的新型解热镇痛药的先导系列设计的宝贵起点。
• 3,5-Bis(trifluoromethyl)pyrazoles:  A Novel Class of NFAT Transcription Factor Regulator
  作者：Stevan W. Djuric、Nwe Y. BaMaung、Anwer Basha、Huaqing Liu、Jay R. Luly、David J. Madar、Richard J. Sciotti、Noah P. Tu、Frank L. Wagenaar、Paul E. Wiedeman、Xun Zhou、Stephen Ballaron、Joy Bauch、Yung-Wu Chen、X. Grace Chiou、Thomas Fey、Donna Gauvin、Earl Gubbins、Gin C. Hsieh、Kennan C. Marsh、Karl W. Mollison、Melissa Pong、Thomas K. Shaughnessy、Michael P. Sheets、Morey Smith、James M. Trevillyan、Usha Warrior、Craig D. Wegner、George W. Carter

  DOI：10.1021/jm990615a

  日期：2000.8.1

  A series of bis(trifluoromethyl)pyrazoles (BTPs) has been found to be a novel inhibitor of cytokine production. Identified initially as inhibitors of IL-2 synthesis, the BTPs have been optimized in this regard and even inhibit IL-2 production with a 10-fold enhancement over cyclosporine in an ex vivo assay. Additionally, the BTPs show inhibition of IL-4, IL-5, IL-8, and eotaxin production. Unlike the IL-2 inhibitors, cycloseorine and FK506, the BTPs do not directly inhibit the dephosphorylation of NFAT by calcineurin.