N-[4-(5-Amino-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-3-fluoro-isonicotinamide | 1028289-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-(5-Amino-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-3-fluoro-isonicotinamide
• 英文别名: N-[4-[5-amino-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-3-fluoropyridine-4-carboxamide
• CAS: 1028289-25-9
• 化学式: C₁₆H₁₁F₄N₅O
• 分子量: 365.29
• InChiKey: DEFONALUJWIIPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[4-(5-Amino-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-3-fluoro-isonicotinamide 在 copper(II) sulfate 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 生成 3-Fluoro-N-[4-(3-trifluoromethyl-pyrazol-1-yl)-phenyl]-isonicotinamide 、 3-fluoro-N-(4-(5-nitro-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)isonicotinamide
  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：

  1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid 在 4-二甲氨基吡啶 、 铁粉 、 氯化铵 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 N-[4-(5-Amino-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-3-fluoro-isonicotinamide
  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

• 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.