(E)-1-(3-trifluoromethylphenyl)-2-(1-p-tolylethylidene)hydrazine

• 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: (E)-1-(3-trifluoromethylphenyl)-2-(1-p-tolylethylidene)hydrazine
• 英文别名: (E)-1-(3-trifluromethylphenyl)-2-(1-p-tolylethylidene)hydrazine；N-[(E)-1-(4-methylphenyl)ethylideneamino]-3-(trifluoromethyl)aniline
• 化学式: C₁₆H₁₅F₃N₂
• 分子量: 292.304
• InChiKey: BUZVUQTUOVIXOZ-UDWIEESQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-trifluoromethylphenyl)-2-(1-p-tolylethylidene)hydrazine 在 Jones reagent 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 18.33h， 生成 3-(p-tolyl)-1-(3-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  [EN] FARNESOID X RECEPTOR ANTAGONISTS
  [FR] ANTAGONISTES DU RÉCEPTEUR X DE FARNÉSOÏDE

  摘要：

  公开号：

  WO2015116856A3
• 作为产物：
  描述：

  3-(三氟甲基)苯肼盐酸盐 、 对甲基苯乙酮 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以93%的产率得到(E)-1-(3-trifluoromethylphenyl)-2-(1-p-tolylethylidene)hydrazine
  参考文献：
  名称：

  Identification of trisubstituted-pyrazol carboxamide analogs as novel and potent antagonists of farnesoid X receptor

  摘要：

  Farnesoid X receptor (FXR, NRIH4) plays a major role in the control of cholesterol metabolism. This suggests that antagonizing the transcriptional activity of FXR is a potential means to treat cholestasis and related metabolic disorders. Here we describe the synthesis, biological evaluation, and structure-activity relationship (SAR) studies of trisubstituted-pyrazol carboxamides as novel and potent FXR antagonists. One of these novel FXR antagonists, 4j has an IC50 of 7.5 nM in an FXR binding assay and 468.5 nM in a cell-based FXR antagonistic assay. Compound 4j has no detectable FXR agonistic activity or cytotoxicity. Notably, 4j is the most potent FXR antagonist identified to date; it has a promising in vitro profile and could serve as an excellent chemical tool to elucidate the biological function of FXR. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.014

文献信息

• The Effect of 1,3-Diaryl-[1H]-pyrazole-4-acetamides on Glucose Utilization in ob/ob Mice
  作者：Gregory R. Bebernitz、Greg Argentieri、Beverly Battle、Christine Brennan、Bork Balkan、Bryan F. Burkey、Michele Eckhardt、Jiaping Gao、Prasad Kapa、Robert J. Strohschein、Herbert F. Schuster、Mary Wilson、David D. Xu

  DOI：10.1021/jm010032c

  日期：2001.8.1

  This article provides evidence of a new class of compounds, 1,3-diaryl-[1H]-pyrazole-4-acetamides, initially identified from their ability to increase glucose transport in an adipocyte and muscle cell line and ultimately demonstrating dramatic glucose lowering in ob/ob Mice, a diabetic animal model. The lead compound, 1, possessed some behavioral-like effects which were removed by structural variation during the course of this investigation. Specifically, 11 g (RI = meta-CF3, Ar2 = 4 ' biphenyl, R3 = diethylamide) illustrated the potency of this series with ED50 values for glucose lowering in ob/ob mice of 3.0 mg/kg/day. Concomitant with its effect on glucose lowering, 11g also caused a 50% reduction in insulin levels consistent with an agent that increases whole body insulin sensitivity. 11g showed favorable pharmacokinetic data with acceptable absorption, negligible metabolism, and good duration of action. 11g demonstrated no appreciable adipogenic effect through PPAR gamma agonism, a characteristic of the thiazolidinediones (TZD), and so represents a potentially new class of agents for the treatment of diabetes.