N4-((2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl)-N6-(2-ethylhexyl)pyrimidine-4,6-diamine | 1187878-16-5

• 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: N4-((2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl)-N6-(2-ethylhexyl)pyrimidine-4,6-diamine
• 英文别名: 4-N-[(2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl]-6-N-(2-ethylhexyl)pyrimidine-4,6-diamine
• CAS: 1187878-16-5
• 化学式: C₂₈H₃₆BrClN₄
• 分子量: 543.978
• InChiKey: CNPDKRZFFANWGF-MPXHWGBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙基己胺 、 N-((2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl)-6-chloropyrimidin-4-amine 反应 1.0h， 生成 N4-((2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl)-N6-(2-ethylhexyl)pyrimidine-4,6-diamine
  参考文献：
  名称：

  Substituted pyrimidines as cannabinoid CB1 receptor ligands

  摘要：

  Cannabinoid CB1 receptors have been the avenue of extensive studies since the first clinical results of rimonabant (SR141716)for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of substituted pyrimidines based on chemical structure of Merck's taranabant, a cannabinoid CB1 receptor inverse agonist. Noticeably, N4-((2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl)-N6-butylpyrimidine-4,6-diamine (13b) demonstrated good binding affinity and decent selectivity for CB1 receptor (IC50 = 16.3 nM, CB2/CB1 = 181.6). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.069

文献信息

• Substituted pyrimidines as cannabinoid CB1 receptor ligands
  作者：Min Ju Kim、Jong Yup Kim、Hee Jeong Seo、Junwon Lee、Sung-Han Lee、Mi-Soon Kim、Jahyo Kang、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2009.06.069

  日期：2009.8

  Cannabinoid CB1 receptors have been the avenue of extensive studies since the first clinical results of rimonabant (SR141716)for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of substituted pyrimidines based on chemical structure of Merck's taranabant, a cannabinoid CB1 receptor inverse agonist. Noticeably, N4-((2S,3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-yl)-N6-butylpyrimidine-4,6-diamine (13b) demonstrated good binding affinity and decent selectivity for CB1 receptor (IC50 = 16.3 nM, CB2/CB1 = 181.6). (C) 2009 Elsevier Ltd. All rights reserved.