1-(2-aminoethyl)-3-[2-({2-[(diaminomethylidene)amino]thiazol-4-yl}methylthio)ethyl]guanidino-2-carbonitrile | 93376-69-3

• 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-(2-aminoethyl)-3-[2-({2-[(diaminomethylidene)amino]thiazol-4-yl}methylthio)ethyl]guanidino-2-carbonitrile
• 英文别名: 2-(2-aminoethyl)-1-cyano-3-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]guanidine
• CAS: 93376-69-3
• 化学式: C₁₁H₁₉N₉S₂
• 分子量: 341.464
• InChiKey: YJUMLFUGBGNKFL-UHFFFAOYSA-N

物化性质

• 沸点：
  541.1±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  163.52
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(2-aminoethyl)-3-[2-({2-[(diaminomethylidene)amino]thiazol-4-yl}methylthio)ethyl]guanidino-2-carbonitrile 在 亚硝酸特丁酯 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 2-acetamido-N-{2-cyano-3-[2-({2-[(diaminomethylidene)amino]thiazol-4-yl}methylthio)ethyl]guanidino}-3-methyl-3-(nitrosothio)butanamide diacetate
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of New H2-Antagonists Containing NO-Donor Moieties, Endowed with Mixed Antisecretory and Gastroprotective Activities

  摘要：

  Synthesis, structural characterization, and pharmacological profile of a series of Hz-antagonists able to release nitric oxide (NO) are reported. These compounds were obtained by using appropriate spacers to join H-2-antagonistic pharmacophoric groups related to lamtidine and tiotidine to different NO-donor moieties such as esters of HNO3, nitrosothio groups, and benzenesulfonyl-substituted furoxans. All of the compounds were tested for their NO-donor properties. Furthermore, the hybrid structures synthesized, together with some selected reference compounds, were tested for their H-2-antagonistic properties, both in vitro and in vivo, and for their gastroprotective effects. Only the hybrid compounds were able both to antagonize histamine effects on guinea-pig papillary muscle and to display in vivo antisecretory and gastroprotective action. The best results were obtained with the lamtidine/furoxan hybrid structure.

  DOI：

  10.1002/(sici)1522-2675(20000119)83:1<287::aid-hlca287>3.0.co;2-2
• 作为产物：
  描述：

  乙二胺 、 N-cyano-N'-[2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethyl]-O-phenyl-isourea 反应 3.0h， 以88%的产率得到1-(2-aminoethyl)-3-[2-({2-[(diaminomethylidene)amino]thiazol-4-yl}methylthio)ethyl]guanidino-2-carbonitrile
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of New H2-Antagonists Containing NO-Donor Moieties, Endowed with Mixed Antisecretory and Gastroprotective Activities

  摘要：

  Synthesis, structural characterization, and pharmacological profile of a series of Hz-antagonists able to release nitric oxide (NO) are reported. These compounds were obtained by using appropriate spacers to join H-2-antagonistic pharmacophoric groups related to lamtidine and tiotidine to different NO-donor moieties such as esters of HNO3, nitrosothio groups, and benzenesulfonyl-substituted furoxans. All of the compounds were tested for their NO-donor properties. Furthermore, the hybrid structures synthesized, together with some selected reference compounds, were tested for their H-2-antagonistic properties, both in vitro and in vivo, and for their gastroprotective effects. Only the hybrid compounds were able both to antagonize histamine effects on guinea-pig papillary muscle and to display in vivo antisecretory and gastroprotective action. The best results were obtained with the lamtidine/furoxan hybrid structure.

  DOI：

  10.1002/(sici)1522-2675(20000119)83:1<287::aid-hlca287>3.0.co;2-2