3-(3-((dimethylamino)methyl)-5-(2,4-dimethylphenyl)-1H-1,2,4-triazol-1-yl)phenol | 915124-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-((dimethylamino)methyl)-5-(2,4-dimethylphenyl)-1H-1,2,4-triazol-1-yl)phenol
• 英文别名: 3-[3-[(dimethylamino)methyl]-5-(2,4-dimethylphenyl)-1,2,4-triazol-1-yl]phenol
• CAS: 915124-94-6
• 化学式: C₁₉H₂₂N₄O
• 分子量: 322.41
• InChiKey: QSSZOJFXUSHIGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5-(2,4-dimethylphenyl)-1-(3-methoxyphenyl)-1H-1,2,4-triazol-3-yl)-N,N-dimethylmethanamine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到3-(3-((dimethylamino)methyl)-5-(2,4-dimethylphenyl)-1H-1,2,4-triazol-1-yl)phenol
  参考文献：
  名称：

  Novel delta opioid receptor agonists exhibit differential stimulation of signaling pathways

  摘要：

  A novel family of 1,3,5-trisubstituted 1,2,4-triazoles was discovered as potent and selective ligands for the delta opioid receptor by rational design. Compound 5b exhibited low-nanomolar in vitro binding affinity (IC50 = 5.8 nM), excellent selectivity for the d opioid receptor over the alternative mu and kappa opioid receptors, full agonist efficacy in receptor down-regulation and MAP kinase activation assays, and low-efficacy partial agonist activity in stimulation of GTP gamma S binding. The apparent discrepancy observed in these functional assays may stem from different signaling pathways involved in each case, as found previously for other G-protein coupled receptors. More biological studies are underway to better understand the differential stimulation of signaling pathways by these novel compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.007

文献信息

• Novel delta opioid receptor agonists exhibit differential stimulation of signaling pathways
  作者：Youyi Peng、Qiang Zhang、Sonia Arora、Susan M. Keenan、Sandhya Kortagere、Kenneth M. Wannemacher、Richard D. Howells、William J. Welsh

  DOI：10.1016/j.bmc.2009.07.007

  日期：2009.9.1

  A novel family of 1,3,5-trisubstituted 1,2,4-triazoles was discovered as potent and selective ligands for the delta opioid receptor by rational design. Compound 5b exhibited low-nanomolar in vitro binding affinity (IC50 = 5.8 nM), excellent selectivity for the d opioid receptor over the alternative mu and kappa opioid receptors, full agonist efficacy in receptor down-regulation and MAP kinase activation assays, and low-efficacy partial agonist activity in stimulation of GTP gamma S binding. The apparent discrepancy observed in these functional assays may stem from different signaling pathways involved in each case, as found previously for other G-protein coupled receptors. More biological studies are underway to better understand the differential stimulation of signaling pathways by these novel compounds. (C) 2009 Elsevier Ltd. All rights reserved.