2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-benzonitrile | 742105-39-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-benzonitrile
• 英文别名: 2-[2-(5-Bromo-2-methoxyphenyl)ethyl]-3-fluorobenzonitrile
• CAS: 742105-39-1
• 化学式: C₁₆H₁₃BrFNO
• 分子量: 334.188
• InChiKey: HTBSZWKMTZSRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-benzonitrile 在 硫化氢 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-[2-(5-bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-thiobenzamide
  参考文献：
  名称：

  Identification of 2-{2-[2-(5-Bromo-2- methoxyphenyl)-ethyl]-3-fluorophenyl}-4,5-dihydro-1H-imidazole (ML00253764), a Small Molecule Melanocortin 4 Receptor Antagonist That Effectively Reduces Tumor-Induced Weight Loss in a Mouse Model

  摘要：

  The melanocortin 4 receptor (MC4R) plays an important role in body weight regulation and energy homeostasis. Administration of peptidic MC4R antagonists (usually by intracerebro ventricular injection) has been shown in the literature to increase body weight and/or food intake in sever rodent models. We report here the identification of a novel nonpeptidic MC4R antagonist and its effects on tumor-induced weight loss in mice following peripheral administration.

  DOI：

  10.1021/jm034244g
• 作为产物：
  描述：

  3-氟-2-甲基苯腈 、 4-溴-2-(溴甲基)-1-甲氧基苯 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-fluoro-benzonitrile
  参考文献：
  名称：

  Identification of 2-{2-[2-(5-Bromo-2- methoxyphenyl)-ethyl]-3-fluorophenyl}-4,5-dihydro-1H-imidazole (ML00253764), a Small Molecule Melanocortin 4 Receptor Antagonist That Effectively Reduces Tumor-Induced Weight Loss in a Mouse Model

  摘要：

  The melanocortin 4 receptor (MC4R) plays an important role in body weight regulation and energy homeostasis. Administration of peptidic MC4R antagonists (usually by intracerebro ventricular injection) has been shown in the literature to increase body weight and/or food intake in sever rodent models. We report here the identification of a novel nonpeptidic MC4R antagonist and its effects on tumor-induced weight loss in mice following peripheral administration.

  DOI：

  10.1021/jm034244g

文献信息

• Synthesis and biological evaluation of imidazole-based small molecule antagonists of the melanocortin 4 receptor (MC4-R)
  作者：Thomas H Marsilje、Jonathan B Roses、Emily F Calderwood、Stephen G Stroud、Nancy E Forsyth、Christopher Blackburn、David L Yowe、Wenyan Miao、Stacey V Drabic、Marie D Bohane、J Scott Daniels、Ping Li、Lijun Wu、Michael A Patane、Christopher F Claiborne

  DOI：10.1016/j.bmcl.2004.05.003

  日期：2004.7

  A novel series of imidazole-based small molecule antagonists of the melanocortin 4 receptor (MC4-R) is reported. Members of this series have been identified, which exhibit sub-micromolar binding affinity for the MC4-R, functional potency <100nM, and good oral exposure in rat. Antagonists of the MC4-R are potentially useful in the therapeutic treatment of involuntary weight loss due to advanced age or disease (e.g. cancer or AIDS), an area of large, unmet medical need. (C) 2004 Elsevier Ltd. All rights reserved.