(2-methyl-1-trityl-1H-imidazol-4-yl)-(1-trifluoromethyl-cyclopropyl)-methanone | 1022154-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2-methyl-1-trityl-1H-imidazol-4-yl)-(1-trifluoromethyl-cyclopropyl)-methanone
• 英文别名: (2-methyl-1-trityl-1H-imidazol-4-yl)[1-(trifluoromethyl)cyclopropyl]methanone；(2-Methyl-1-trityl-1H-imidazol-4-YL)(1-(trifluoromethyl)cyclopropyl)methanone；(2-methyl-1-tritylimidazol-4-yl)-[1-(trifluoromethyl)cyclopropyl]methanone
• CAS: 1022154-58-0
• 化学式: C₂₈H₂₃F₃N₂O
• 分子量: 460.499
• InChiKey: RDRHEUOGYGMBBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-methyl-1-trityl-1H-imidazol-4-yl)-(1-trifluoromethyl-cyclopropyl)-methanone 在 正丁基锂 、 一水合肼 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 乙二醇 为溶剂， 反应 5.25h， 生成 2-(4-(1H-pyrazol-1-yl)phenyl)-1,1,1-trifluoro-3-(4-((1-(trifluoromethyl)cyclopropyl)methyl)-1-trityl-1H-imidazol-2-yl)propan-2-ol
  参考文献：
  名称：

  Discovery of MK-5046, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Obesity

  摘要：

  We report the development and characterization of compound 22 (MK-5046), a potent, selective small molecule agonist of BRS-3 (bombesin receptor subtype-3). In pharmacological testing using diet-induced obese mice, compound 22 caused mechanism-based, dose-dependent reductions in food intake and body weight.

  DOI：

  10.1021/ml100196d
• 作为产物：
  描述：

  1-三氟甲基环丙烷-1-羧酸 在 N-甲基吗啉 、 乙基溴化镁 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 (2-methyl-1-trityl-1H-imidazol-4-yl)-(1-trifluoromethyl-cyclopropyl)-methanone
  参考文献：
  名称：

  Discovery of MK-5046, a Potent, Selective Bombesin Receptor Subtype-3 Agonist for the Treatment of Obesity

  摘要：

  We report the development and characterization of compound 22 (MK-5046), a potent, selective small molecule agonist of BRS-3 (bombesin receptor subtype-3). In pharmacological testing using diet-induced obese mice, compound 22 caused mechanism-based, dose-dependent reductions in food intake and body weight.

  DOI：

  10.1021/ml100196d

文献信息

• Substituted inmidazoles as bombesin receptor subtype-3 modulators
  申请人：Chen David

  公开号：US20100022598A1

  公开（公告）日：2010-01-28

  Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代咪唑是人类炸弹素受体的配体，特别是人类炸弹素受体亚型-3（BRS-3）的选择性配体。因此，它们对于治疗、控制或预防对BRS-3调节敏感的疾病和紊乱，如肥胖症和糖尿病，具有用处。
• A Practical, Kilogram-Scale Implementation of the Wolff−Kishner Reduction
  作者：Jeffrey T. Kuethe、Karla G. Childers、Zhihui Peng、Michel Journet、Guy R. Humphrey、Thomas Vickery、Donald Bachert、Thientu T. Lam

  DOI：10.1021/op9000274

  日期：2009.5.15

  preparation of imidazole 7. The key transformation involved the Wolff−Kishner reduction of the sterically demanding neopentyl-trifluoromethylcyclopropyl imidazole ketone 8. The described process provided the desired product in 74% overall yield without recourse to chromatographic purification. Safety considerations which allowed for the reaction to be conducted safely on kilogram scale are discussed.

  对于大规模制备咪唑7，已经开发出一种安全实用的策略。关键的转变涉及空间需求的新戊基-三氟甲基环丙基咪唑酮8的Wolff-Kishner还原。所描述的方法以74％的总收率提供了所需产物，而无需进行色谱纯化。讨论了安全考虑，使反应可以在千克规模上安全进行。
• Substituted imidazole as bombesin receptor subtype-3 modulators
  申请人：Merck Sharp & Dohme Corp.

  公开号：US08193228B2

  公开（公告）日：2012-06-05

  Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代咪唑是人类炸弹素受体的配体，特别是人类炸弹素受体亚型-3（BRS-3）的选择性配体。因此，它们可用于治疗、控制或预防对BRS-3调节敏感的疾病和障碍，如肥胖症和糖尿病。
• SUBSTITUTED IMIDAZOLES AS BOMBESIN RECEPTOR SUBTYPE-3 MODULATORS
  申请人：Merck & Co., Inc.

  公开号：EP2091937A2

  公开（公告）日：2009-08-26
• US8193228B2
  申请人：——

  公开号：US8193228B2

  公开（公告）日：2012-06-05