2-[(5-Methyl-1-tritylimidazol-4-yl)methyl]-6-oxidobenzo[h][2,6]naphthyridin-6-ium-1-one | 143075-61-0

• 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-[(5-Methyl-1-tritylimidazol-4-yl)methyl]-6-oxidobenzo[h][2,6]naphthyridin-6-ium-1-one
• CAS: 143075-61-0
• 化学式: C₃₆H₂₈N₄O₂
• 分子量: 548.644
• InChiKey: DSLKCJCKXBXHMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(5-Methyl-1-tritylimidazol-4-yl)methyl]-6-oxidobenzo[h][2,6]naphthyridin-6-ium-1-one 在 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以34%的产率得到2-[(5-methyl-1-tritylimidazol-4-yl)methyl]-6H-benzo[c][2,6]naphthyridine-1,5-dione
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Isoquinolinones and 3-aryl-2-pyridones

  摘要：

  Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists are described. The key pharmacophoric elements were defined as a basic nitrogen, a group capable of hydrogen bonding interactions, and an aromatic moiety. 1,2-Dihydro-2-oxopyridine moiety could be a good linking group because of its nicely planar structure. The steric limitations of the aromatic moiety were investigated by X-ray analysis and computer analysis and shown to be optimal when the aromatic moiety was constrained within an arched planar system, which could be successfully replaced by 3-(2-thienyl)-2-oxopyridine function or 6-amino-7-chloro-1-isoquinolinone function without any loss of the activity. Among the synthesized compounds, 42 showed the most potent activity in the inhibition of Bezold-Jarisch reflex in rats. Compounds 44a and 64 were orally active in the protection against cisplatin-induced emesis in dogs or ferrets. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00096a001
• 作为产物：
  描述：

  4-(氯甲基)-5-甲基-1-(三苯基甲基)-1H-咪唑 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 24.33h， 生成 2-[(5-Methyl-1-tritylimidazol-4-yl)methyl]-6-oxidobenzo[h][2,6]naphthyridin-6-ium-1-one
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Isoquinolinones and 3-aryl-2-pyridones

  摘要：

  Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists are described. The key pharmacophoric elements were defined as a basic nitrogen, a group capable of hydrogen bonding interactions, and an aromatic moiety. 1,2-Dihydro-2-oxopyridine moiety could be a good linking group because of its nicely planar structure. The steric limitations of the aromatic moiety were investigated by X-ray analysis and computer analysis and shown to be optimal when the aromatic moiety was constrained within an arched planar system, which could be successfully replaced by 3-(2-thienyl)-2-oxopyridine function or 6-amino-7-chloro-1-isoquinolinone function without any loss of the activity. Among the synthesized compounds, 42 showed the most potent activity in the inhibition of Bezold-Jarisch reflex in rats. Compounds 44a and 64 were orally active in the protection against cisplatin-induced emesis in dogs or ferrets. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00096a001