1-(4-Methylphenyl)-3-hydroxy-4,4,4-trifluoro-2-butene-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(4-Methylphenyl)-3-hydroxy-4,4,4-trifluoro-2-butene-1-one
• 英文别名: 1,1,1-trifluoro-4-hydroxy-4-(4-methylphenyl)but-3-en-2-one
• 化学式: C₁₁H₉F₃O₂
• 分子量: 230.186
• InChiKey: RHQUXXUCBVNJCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-Methylphenyl)-3-hydroxy-4,4,4-trifluoro-2-butene-1-one 、 4-肼基苯甲酸 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzoic acid
  参考文献：
  名称：

  A novel celecoxib analog UTX-121 inhibits HT1080 cell invasion by modulating membrane-type 1 matrix metalloproteinase

  摘要：

  We designed and synthesized a celecoxib derivative UTX-121 to enhance its anti-tumor activity. Similar to celecoxib, this compound could also inhibit matrix metalloproteinase (MMP)-9 activity. In addition, UTX-121 suppressed membrane-type 1 MMP (MT1-MMP)-mediated pro-MMP-2 activation by disturbing the cell surface expression of MT1-MMP. UTX-121 also impeded the glycosylation of cell surface proteins, resulting in the suppression of cell attachment to fibronectin. This inhibition by UTX-121 caused the reduction of fibronectin-stimulated focal adhesion kinase activation, Alt activation, and cell migration. Consequently, UTX-121 treatment significantly inhibited fibronectin-induced HT1080 cell invasion into the Matrigel. UTX-121 may be a potent lead compound that can be used to develop a novel anti-tumor drug. (C) 2019 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2019.10.092
• 作为产物：
  描述：

  三氟乙酸乙酯 、 对甲基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 1-(4-Methylphenyl)-3-hydroxy-4,4,4-trifluoro-2-butene-1-one
  参考文献：
  名称：

  A novel celecoxib analog UTX-121 inhibits HT1080 cell invasion by modulating membrane-type 1 matrix metalloproteinase

  摘要：

  We designed and synthesized a celecoxib derivative UTX-121 to enhance its anti-tumor activity. Similar to celecoxib, this compound could also inhibit matrix metalloproteinase (MMP)-9 activity. In addition, UTX-121 suppressed membrane-type 1 MMP (MT1-MMP)-mediated pro-MMP-2 activation by disturbing the cell surface expression of MT1-MMP. UTX-121 also impeded the glycosylation of cell surface proteins, resulting in the suppression of cell attachment to fibronectin. This inhibition by UTX-121 caused the reduction of fibronectin-stimulated focal adhesion kinase activation, Alt activation, and cell migration. Consequently, UTX-121 treatment significantly inhibited fibronectin-induced HT1080 cell invasion into the Matrigel. UTX-121 may be a potent lead compound that can be used to develop a novel anti-tumor drug. (C) 2019 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2019.10.092