3-(4-(2-(4-(2,2-dimethylbutyl)-1H-imidazol-2-yl)ethyl)phenyl)pyridine | 1021937-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4-(2-(4-(2,2-dimethylbutyl)-1H-imidazol-2-yl)ethyl)phenyl)pyridine
• 英文别名: 3-[4-[2-[5-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl]phenyl]pyridine
• CAS: 1021937-27-8
• 化学式: C₂₂H₂₇N₃
• 分子量: 333.476
• InChiKey: XIDSDIGHYCDNCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴吡啶 、 tert-butyl 4-(2,2-dimethylbutyl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)-1H-imidazole-1-carboxylate 在 bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0) 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-(2-(4-(2,2-dimethylbutyl)-1H-imidazol-2-yl)ethyl)phenyl)pyridine
  参考文献：
  名称：

  Synthesis and SAR of derivatives based on 2-biarylethylimidazole as bombesin receptor subtype-3 (BRS-3) agonists for the treatment of obesity

  摘要：

  This Letter describes a series of potent and selective BRS-3 agonists containing a biarylethylimidazole pharmacophore. Extensive SAR studies were carried out with different aryl substitutions. This work led to the identification of a compound 2-{2-[4-(pyridin-2-yl) phenyl] ethyl}-5-(2,2-dimethylbutyl)-1H-imidazole 9 with excellent binding affinity (IC(50) = 18 nM, hBRS-3) and functional agonist activity (EC(50) = 47 nM, 99% activation). After oral administration, compound 9 had sufficient exposure in diet induced obese mice to demonstrate efficacy in lowering food intake and body weight via BRS-3 activation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.076

文献信息

• Synthesis and SAR of derivatives based on 2-biarylethylimidazole as bombesin receptor subtype-3 (BRS-3) agonists for the treatment of obesity
  作者：Jian Liu、Shuwen He、Tianying Jian、Peter H. Dobbelaar、Iyassu K. Sebhat、Linus S. Lin、Allan Goodman、Cheng Guo、Peter R. Guzzo、Mark Hadden、Alan J. Henderson、Kevin Pattamana、Megan Ruenz、Bruce J Sargent、Brian Swenson、Larry Yet、Constantin Tamvakopoulos、Qianping Peng、Jie Pan、Yanqing Kan、Oksana Palyha、Theresa M. Kelly、Xiao-Ming Guan、Andrew D. Howard、Donald J. Marsh、Joseph M. Metzger、Marc L. Reitman、Matthew J. Wyvratt、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2010.02.076

  日期：2010.4

  This Letter describes a series of potent and selective BRS-3 agonists containing a biarylethylimidazole pharmacophore. Extensive SAR studies were carried out with different aryl substitutions. This work led to the identification of a compound 2-2-[4-(pyridin-2-yl) phenyl] ethyl}-5-(2,2-dimethylbutyl)-1H-imidazole 9 with excellent binding affinity (IC(50) = 18 nM, hBRS-3) and functional agonist activity (EC(50) = 47 nM, 99% activation). After oral administration, compound 9 had sufficient exposure in diet induced obese mice to demonstrate efficacy in lowering food intake and body weight via BRS-3 activation. (C) 2010 Elsevier Ltd. All rights reserved.