5-(m-tolyl)-1,3,5-triazaspiro[5.5]undeca-1,3-diene-2,4-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5-(m-tolyl)-1,3,5-triazaspiro[5.5]undeca-1,3-diene-2,4-diamine
• 英文别名: 5-m-Tolyl-1,3,5-triaza-spiro[5.5]undeca-1,3-diene-2,4-diamine；5-(3-methylphenyl)-1,3,5-triazaspiro[5.5]undeca-1,3-diene-2,4-diamine
• 化学式: C₁₅H₂₁N₅
• 分子量: 271.365
• InChiKey: YNNMFPKTGNGOMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(m-tolyl)-1,3,5-triazaspiro[5.5]undeca-1,3-diene-2,4-diamine 以 吡啶 、 乙醇 为溶剂， 以40%的产率得到N⁴-(m-tolyl)-1,3,5-triazaspiro[5.5]undeca-1,3-diene-2,4-diamine
  参考文献：
  名称：

  Exploring Halogen Bonds in 5-Hydroxytryptamine 2B Receptor–Ligand Interactions

  摘要：

  Here, we predicted the potential halogen bonding interaction between compound 2 and the 5-hydroxytryptamine 2B (5-HT2B) receptor and systematically assessed this interaction via structure activity relationship analysis and molecular dynamics simulations. A physics-based computational protocol was then developed to further explore the opportunity of "designing in" halogen bonding interactions in structure-based ligand design for the 5-HT2B receptor, which not only facilitated the identification of previously uncharacterized halogen bonds in known 5-HT2B ligands but also enabled the rational design of halogen bonding interactions for the optimization of 5-HT2B ligands. As a proof-of-concept, a series of halogen-substituted analogues of doxepin synthesized and evaluated, which showed improved in vitro and in vivo potency.

  DOI：

  10.1021/acsmedchemlett.8b00300
• 作为产物：
  描述：

  3-甲基苯胺 、 环己酮 、 二聚氰胺 在 盐酸 作用下， 以 乙醇 为溶剂， 以21%的产率得到5-(m-tolyl)-1,3,5-triazaspiro[5.5]undeca-1,3-diene-2,4-diamine
  参考文献：
  名称：

  Exploring Halogen Bonds in 5-Hydroxytryptamine 2B Receptor–Ligand Interactions

  摘要：

  Here, we predicted the potential halogen bonding interaction between compound 2 and the 5-hydroxytryptamine 2B (5-HT2B) receptor and systematically assessed this interaction via structure activity relationship analysis and molecular dynamics simulations. A physics-based computational protocol was then developed to further explore the opportunity of "designing in" halogen bonding interactions in structure-based ligand design for the 5-HT2B receptor, which not only facilitated the identification of previously uncharacterized halogen bonds in known 5-HT2B ligands but also enabled the rational design of halogen bonding interactions for the optimization of 5-HT2B ligands. As a proof-of-concept, a series of halogen-substituted analogues of doxepin synthesized and evaluated, which showed improved in vitro and in vivo potency.

  DOI：

  10.1021/acsmedchemlett.8b00300