2-(4-bromo-phenyl)-N-(3-trifluoromethyl-phenyl)-acetamide | 349420-02-6

• 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: 2-(4-bromo-phenyl)-N-(3-trifluoromethyl-phenyl)-acetamide
• 英文别名: 2-(4-bromophenyl)-N-[3-(trifluoromethyl)phenyl]acetamide
• CAS: 349420-02-6
• 化学式: C₁₅H₁₁BrF₃NO
• mdl: MFCD02038822
• 分子量: 358.158
• InChiKey: YOMWLPJTQRHOCP-UHFFFAOYSA-N

物化性质

• 沸点：
  463.0±45.0 °C(Predicted)
• 密度：
  1.537±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-phenyl)-N-(3-trifluoromethyl-phenyl)-acetamide 在 potassium fluoride 、 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 lithium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 (S)-1-(5-(4-(2-oxo-2-((3-(trifluoromethyl)phenyl)amino)ethyl)phenyl)picolinoyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Discovery of a low-systemic-exposure DGAT-1 inhibitor with a picolinoylpyrrolidine-2-carboxylic acid moiety

  摘要：

  A series of diacylglycerol O-acyltransferase 1 (DGAT-1) inhibitors with a picolinoylpyrrolidine2-carboxylic acid moiety were designed and synthesized. Of these compounds, compound 22 exhibited excellent DGAT-1-inhibitory activity (hDGAT-1 enzyme assay, 50% inhibitory concentration [IC50] = 3.5 +/- 0.9 nM) and effectively reduced the intracellular triglyceride contents in 3T3-L1, HepG2 and Caco-2 cells. A preliminary study of the plasma and tissue distributions of compound 22 in mice revealed low plasma exposure and high concentrations in different segments of the intestine and liver, which may facilitate targeting DGAT-1. Furthermore, in an acute lipid challenge test, compound 22 showed a dose-dependent inhibitory effect on high-serum triglycerides in C57/KSJ mice induced by olive oil (1, 3, and 10 mg/kg, i.g.). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.007
• 作为产物：
  描述：

  间氨基三氟甲苯 、 对溴苯乙酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以97%的产率得到2-(4-bromo-phenyl)-N-(3-trifluoromethyl-phenyl)-acetamide
  参考文献：
  名称：

  Discovery of a low-systemic-exposure DGAT-1 inhibitor with a picolinoylpyrrolidine-2-carboxylic acid moiety

  摘要：

  A series of diacylglycerol O-acyltransferase 1 (DGAT-1) inhibitors with a picolinoylpyrrolidine2-carboxylic acid moiety were designed and synthesized. Of these compounds, compound 22 exhibited excellent DGAT-1-inhibitory activity (hDGAT-1 enzyme assay, 50% inhibitory concentration [IC50] = 3.5 +/- 0.9 nM) and effectively reduced the intracellular triglyceride contents in 3T3-L1, HepG2 and Caco-2 cells. A preliminary study of the plasma and tissue distributions of compound 22 in mice revealed low plasma exposure and high concentrations in different segments of the intestine and liver, which may facilitate targeting DGAT-1. Furthermore, in an acute lipid challenge test, compound 22 showed a dose-dependent inhibitory effect on high-serum triglycerides in C57/KSJ mice induced by olive oil (1, 3, and 10 mg/kg, i.g.). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.007

文献信息

• IMIDAZO[1,2-A]PYRIDINE COMPOUNDS AS VEGF-R2 INHIBITORS
  申请人：Barda David Anthony

  公开号：US20090227622A1

  公开（公告）日：2009-09-10

  The present invention provides compounds that are inhibitors of VEGF-R2 of the formula: (I) and methods of using these compounds.

  本发明提供了公式（I）的VEGF-R2抑制剂化合物以及使用这些化合物的方法。
• Imidazo[1,2-A]pyridine compounds as VEGF-R2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US07666879B2

  公开（公告）日：2010-02-23

  The present invention provides compounds that are inhibitors of VEGF-R2 of the formula: (I) and methods of using these compounds.

  本发明提供了公式为(I)的抑制VEGF-R2的化合物以及使用这些化合物的方法。
• WO2006/91671
  申请人：——

  公开号：——

  公开（公告）日：——
• US7666879B2
  申请人：——

  公开号：US7666879B2

  公开（公告）日：2010-02-23
• [EN] IMIDAZO (1, 2-A) PYRIDINE COMPOUNDS AS VEGF-R2 INHIBITORS<br/>[FR] INHIBITEURS DU VEGF-R2 ET PROCEDES
  申请人：LILLY CO ELI

  公开号：WO2006091671A1

  公开（公告）日：2006-08-31

  [EN] The present invention provides compounds that are inhibitors of VEGF-R2 of the formula: (I) and methods of using these compounds.
  [FR] La présente invention concerne composés inhibiteurs du VEGF-R2 (récepteur 2 du facteur de croissance de l'endothélium vasculaire) représentés par la formule (I). L'invention concerne également des procédés d'utilisation de ces composés.