1-(4-Methanesulfinyl-phenyl)-5-p-tolyl-3-trifluoromethyl-1H-pyrazole | 190711-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-Methanesulfinyl-phenyl)-5-p-tolyl-3-trifluoromethyl-1H-pyrazole
• 英文别名: 1-(4-(methylsulfinyl)phenyl)-5-p-tolyl-3-(trifluoromethyl)-1H-pyrazole；5-(4-methylphenyl)-1-(4-methylsulfinylphenyl)-3-(trifluoromethyl)pyrazole
• CAS: 190711-47-8
• 化学式: C₁₈H₁₅F₃N₂OS
• 分子量: 364.391
• InChiKey: BIIFONWAUMRJCE-UHFFFAOYSA-N

物化性质

• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-Methanesulfinyl-phenyl)-5-p-tolyl-3-trifluoromethyl-1H-pyrazole 在 ammonium hydroxide 、 sodium hydroxide 、 磺酰氯 、 sodium acetate 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 塞来西布
  参考文献：
  名称：

  Remarkably Mild and Simple Preparations of Sulfinates, Sulfonyl Chlorides and Sulfonamides from Thioanisoles

  摘要：

  开发了新的高产率程序，将硫代苯甲醚转换为多种用途的磺酰氯衍生物，这一过程通过战略性地利用Pummerer反应实现。

  DOI：

  10.1055/s-1997-801
• 作为产物：
  描述：

  1-(4-(methylthio)phenyl)-5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazole 在 叔丁基过氧化氢 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 various solvents 为溶剂， 反应 4.0h， 以87%的产率得到1-(4-Methanesulfinyl-phenyl)-5-p-tolyl-3-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  CYP2C9 Structure−Metabolism Relationships:  Optimizing the Metabolic Stability of COX-2 Inhibitors

  摘要：

  The cytochrome P450 (CYP) family is composed of a large group of monooxygenases that mediate the metabolism of xenobiotics and endogenous compounds. CYP2C9, one of the major isoforms of the CYP family, is responsible for the phase I metabolism of a variety of drugs. The aim of the present investigation is to use rational design together with MetaSite, a metabolism site prediction program, to synthesize compounds that retain their pharmacological effects but that are metabolically more stable in the presence of CYP2C9. The model compound for the study is the nonsteroidal anti-inflammatory drug celecoxib, a COX-2 selective inhibitor and known CYP2C9 substrate. Thirteen analogs of celecoxib were designed, synthesized, and evaluated with regard to their metabolic properties and pharmacologic effects. The docking solutions and the predictions from MetaSite gave useful information leading to the design of new compounds with improved metabolic properties.

  DOI：

  10.1021/jm0705096