N-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]thiourea | 38603-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]thiourea
• 英文别名: N-<2-<<(5-methyl-1H-imidazol-4-yl)methyl>thio>ethyl>thiourea；N-<2-<(5(4)-methyl-4(5)-imidazolyl)-methylthio>-ethyl>-thioharnstoff；N-(2<(5-methyl-4-imidazolyl)methylthio>ethyl)thiourea；[2-(5-methyl-1(3)H-imidazol-4-ylmethylsulfanyl)-ethyl]-thiourea；N-[2-((5-methyl-4-imidazolyl)methylthio) ethyl]thiourea；n-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-thiourea；2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylthiourea
• CAS: 38603-54-2
• 化学式: C₈H₁₄N₄S₂
• 分子量: 230.358
• InChiKey: XSAXLPYZTXJUDU-UHFFFAOYSA-N

物化性质

• 熔点：
  109-111 °C
• 沸点：
  494.6±55.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]thiourea 以 甲醇 、 水 、 丙酮 为溶剂， 反应 21.0h， 生成 N-<2-<<(5-methyl-1H-imidazol-4-yl)methyl>thio>ethyl>-N'-<3-(thiazol-2-yl)propyl>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-(((5-甲基-1H-咪唑-4-基)甲基)硫代)乙胺 在 水 、 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 N-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]thiourea
  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

• Guanidino, thioureido and isothioureido derivatives containing imidazole
  申请人：Smith Kline & French Laboratories Limited

  公开号：US03968227A1

  公开（公告）日：1976-07-06

  The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N" -disubstituted guanidino), N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido) groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.

  化合物为C2-C8直链烷烃，末端被N-(N'-取代胍基)、N-(N',N"-二取代胍基)、N-(N'-取代硫脲基)、N-(硝甲基亚胺基)或S-(N-取代异硫脲基)对称或不对称取代。本发明的两种化合物是1,3-双[N'-(2-(5-甲基-4-咪唑基甲硫基)乙基)胍基]丙烷和1,3-双[S-(N-2-(5-甲基-4-咪唑基甲硫基)乙基)异硫脲基]丙烷。本发明的化合物是H-2组胺受体的抑制剂。
• 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。
• Nitromethylene amidino derivatives containing imidazole groups
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04151289A1

  公开（公告）日：1979-04-24

  The compunds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.

  该化合物是C.sub.2-C.sub.8直链烷基，通过N-（N'-取代的鸟氨酸基），N-（N'，N"-二取代的鸟氨酸基），N-（N'-取代的硫脲基），N-（亚硝基甲亚胺基）或S-（N-取代的异硫脲基）末端取代的对称或非对称化合物。本发明的两种化合物是1,3-双-[N'-(2-(5-甲基-4-咪唑甲基硫基)乙基)鸟氨酸基]丙烷和1,3-双-[S-(N-2-(5-甲基-4-咪唑甲基硫基)乙基)异硫脲基]丙烷。本发明化合物是H-2组胺受体的抑制剂。
• Heterocyclic thioureas, isothioureas, guanidines and
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04405621A1

  公开（公告）日：1983-09-20

  The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.

  该化合物是C.sub.2-C.sub.8直链烷基，通过N-(N'-取代基)guanidino、N-(N',N"-二取代基)guanidino、N-(N'-取代硫脲基)、N-(硝基亚甲基酰胺基)或S-(N-取代异硫脲基)基端置换的对称或不对称化合物。本发明的两种化合物是1,3-双-[N'-(2-(5-甲基-4-咪唑基甲硫基)乙基)guanidino]丙烷和1,3-双-[S-(N-2-(5-甲基-4-咪唑基甲硫基)乙基)异硫脲基]丙烷。本发明化合物是H-2组胺受体的抑制剂。
• Imidazolyl thioureas, ureas and guanidines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04152443A1

  公开（公告）日：1979-05-01

  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，脲和鸟氨酸，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）甲基硫基）乙基]硫脲和N，N'-双[2-（（4-甲基-5-咪唑基）甲基硫基）乙基]-N''-氰基鸟氨酸。