2-[(2-{[(4-methyl-5-imidazolyl)methyl]thio}ethyl)amino]-3-nitropyrid-4-one | 99035-20-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-[(2-{[(4-methyl-5-imidazolyl)methyl]thio}ethyl)amino]-3-nitropyrid-4-one
• 英文别名: Cimetidine,2-(3-nitropyridin-4-one)；2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-3-nitro-1H-pyridin-4-one
• CAS: 99035-20-8
• 化学式: C₁₂H₁₅N₅O₃S
• 分子量: 309.349
• InChiKey: SUNQRMGMDYEUBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-bromo-3-nitropyridin-4-ol 、 2-(((5-甲基-1H-咪唑-4-基)甲基)硫代)乙胺 反应 0.5h， 生成 2-[(2-{[(4-methyl-5-imidazolyl)methyl]thio}ethyl)amino]-3-nitropyrid-4-one
  参考文献：
  名称：

  Dipole moment in relation to hydrogen receptor histamine antagonist activity for cimetidine analogs

  摘要：

  The activities of a series of H2 receptor histamine antagonists structurally related to cimetidine (1) have been compared to investigate the effect of replacing the cyanoguanidine moiety by other neutral, dipolar groups. Antagonist activity, as measured in vitro on the histamine-stimulated guinea pig right atrium, was found to be very sensitive to relatively minor structural changes. Differences in H2 antagonist activity are accounted for by dipole moment orientation and lipophilicity and are rationalized in terms of an optimum requirement for alignment of a hydrogen-bonding moiety in the antagonist with respect to the receptor and desolvation effects at the receptor. The most active compound in the series is the 2-amino-3-nitropyrrole derivative 5, which combines a near-optimal dipole orientation with high lipophilicity.

  DOI：

  10.1021/jm00151a007