9,10-dihydro-9-<<5(4)-methyl-4(5)-imidazolyl>methyl>-10-oxopyrido<4,3-h>quinoline | 143074-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 9,10-dihydro-9-<<5(4)-methyl-4(5)-imidazolyl>methyl>-10-oxopyrido<4,3-h>quinoline
• 英文别名: 9-[(5-methyl-1H-imidazol-4-yl)methyl]-1,9-phenanthrolin-10-one
• CAS: 143074-88-8
• 化学式: C₁₇H₁₄N₄O
• 分子量: 290.324
• InChiKey: JWLSDZFNRYLTIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 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 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 14.33h， 生成 9,10-dihydro-9-<<5(4)-methyl-4(5)-imidazolyl>methyl>-10-oxopyrido<4,3-h>quinoline
  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