N-cyano-N'-{2-[(thiazol-2-yl)methylthio]ethyl}-S-methylisothiourea | 63809-73-4

• 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-cyano-N'-{2-[(thiazol-2-yl)methylthio]ethyl}-S-methylisothiourea
• 英文别名: N-cyano-N'-[2-(2-thiazolylmethylthio)ethyl]-S-methylisothiourea；N-cyano-N'-[2-(2-thiazolylmethyl-thio)ethyl]-S-methylisothiourea；methyl N-cyano-N'-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]carbamimidothioate
• CAS: 63809-73-4
• 化学式: C₉H₁₂N₄S₃
• 分子量: 272.419
• InChiKey: LKNLKECPLBYQOR-UHFFFAOYSA-N

物化性质

• 沸点：
  403.8±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-cyano-N'-{2-[(thiazol-2-yl)methylthio]ethyl}-S-methylisothiourea 在 盐酸 作用下， 反应 3.0h， 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 24.0h， 生成 N-cyano-N'-{2-[(thiazol-2-yl)methylthio]ethyl}-S-methylisothiourea
  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

• Pharmacologically active guanidine compounds
  申请人：Smith Kline & French Laboratories Limited

  公开号：US03950333A1

  公开（公告）日：1976-04-13

  The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.

  这些化合物是取代的硫代烷基、氨基烷基和氧烷基胍，它们是组胺活性的抑制剂。
• Thiazole derivatives
  申请人：Bristol-Myers Company

  公开号：US04200578A1

  公开（公告）日：1980-04-29

  Compounds of the formula ##STR1## wherein R.sup.1 is a straight or branched chain alkynyl group containing from 3 to 9 carbon atoms, inclusive; R.sup.2 and R.sup.3 each are independently hydrogen, (lower)alkyl, guanidino or --(CH.sub.2).sub.p NR.sup.4 R.sup.5 ; R.sup.4 and R.sup.5 each are independently hydrogen, (lower)alkyl or phenyl; n is 2 or 3; p is 1, 2 or 3; X is NR.sup.6 or CHR.sup.6 ; R.sup.6 is cyano, nitro, SO.sub.2 Ar or SO.sub.2 (lower)alkyl; and Ar is phenyl or phenyl containing 1 or 2 substituents selected from halogen and (lower)alkyl; and nontoxic, pharmaceutically acceptable salts thereof, are potent anti-ulcer agents.

  式为##STR1##的化合物，其中R.sup.1是含有3至9个碳原子的直链或支链炔基团；R.sup.2和R.sup.3分别独立地是氢、(较低)烷基、胍基或--(CH.sub.2).sub.p NR.sup.4 R.sup.5；R.sup.4和R.sup.5分别独立地是氢、(较低)烷基或苯基；n为2或3；p为1、2或3；X为NR.sup.6或CHR.sup.6；R.sup.6为氰基、硝基、SO.sub.2 Ar或SO.sub.2 (较低)烷基；Ar为苯基或含有1或2个卤素和(较低)烷基的苯基；以及其无毒、药用可接受的盐，是有效的抗溃疡药物。
• 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。
• 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。
• N-Heterocyclic alkyl-N'-thiadiazolyl, thiazolyl and isothiazolyl
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04388319A1

  公开（公告）日：1983-06-14

  The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. A compound of this invention is N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-[2-(2-thiazolyl methylthio)ethyl]guanidine.

  这些化合物是N,N'-取代硫脲、脲和鸟氨酸类物质，它们是H-2组胺受体抑制剂。该发明的一种化合物是N-氰基-N'-[2-((4-甲基-5-咪唑基)甲硫基)乙基]-N"-[2-(2-噻唑甲硫基)乙基]鸟氨酸。