1-cyano-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-2-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]guanidine | 63779-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-cyano-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-2-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]guanidine
• CAS: 63779-32-8
• 化学式: C₁₅H₂₁N₇S₃
• 分子量: 395.577
• InChiKey: CKSKVWHYYTZWTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-cyano-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-2-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]guanidine 在 盐酸 作用下， 生成 N-<2-<<(5-methyl-1H-imidazol-4-yl)methyl>thio>ethyl>-N'-<2-<(thiazol-2-yl-methyl)thio>ethyl>guanidine
  参考文献：
  名称：

  The histamine H2-receptor agonist impromidine: synthesis and structure activity considerations

  摘要：

  Impromidine (1) is a potent and selective histamine H2 receptor agonist and its structure comprises a strongly basic guanidine group containing two different imidazole-containing side chains. In this paper we report the synthesis of analogues in which both of the side chains and the guanidine group are modified and tested as agonists or antagonists at histamine H2 receptors on guinea pig atrium. A protonated amidine group linked by a chain of three carbon atoms to a tautomeric imidazole ring appears to be an essential feature for agonist activity and it is suggested that the second imidazole-containing side chain in impromidine mainly contributes toward affinity for histamine H2 receptors.

  DOI：

  10.1021/jm00148a007
• 作为产物：
  描述：

  2-[(2-thiazolylmethyl)thio]ethylamine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 1-cyano-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]-2-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]guanidine
  参考文献：
  名称：

  The histamine H2-receptor agonist impromidine: synthesis and structure activity considerations

  摘要：

  Impromidine (1) is a potent and selective histamine H2 receptor agonist and its structure comprises a strongly basic guanidine group containing two different imidazole-containing side chains. In this paper we report the synthesis of analogues in which both of the side chains and the guanidine group are modified and tested as agonists or antagonists at histamine H2 receptors on guinea pig atrium. A protonated amidine group linked by a chain of three carbon atoms to a tautomeric imidazole ring appears to be an essential feature for agonist activity and it is suggested that the second imidazole-containing side chain in impromidine mainly contributes toward affinity for histamine H2 receptors.

  DOI：

  10.1021/jm00148a007

文献信息

• Certain thiazoles and oxazoles
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04025527A1

  公开（公告）日：1977-05-24

  The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. Two compounds of this invention are N,N'-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea and N,N'-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-cyanoguanidine.

  这些化合物是N,N'-取代硫脲、尿素和胍胺，它们是H-2组胺受体抑制剂。本发明的两种化合物是N,N'-双[2-((4-甲基-5-咪唑基)甲硫基)乙基]硫脲和N,N'-双[2-((4-甲基-5-咪唑基)甲硫基)乙基]-N"-氰基胍胺。
• DURANT, G. J.;GANELLIN, C. R.;HILLS, D. W.;MILES, P. D.;PARSONS, M. E.;PE+, J. MED. CHEM., 1985, 28, N 10, 1414-1422
  作者：DURANT, G. J.、GANELLIN, C. R.、HILLS, D. W.、MILES, P. D.、PARSONS, M. E.、PE+

  DOI：——

  日期：——
• US4025527A
  申请人：——

  公开号：US4025527A

  公开（公告）日：1977-05-24
• US4112104A
  申请人：——

  公开号：US4112104A

  公开（公告）日：1978-09-05
• US4152443A
  申请人：——

  公开号：US4152443A

  公开（公告）日：1979-05-01