3-{[(cyanoimino)(phenoxy)methyl]amino}propyl nitrate | 263163-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-{[(cyanoimino)(phenoxy)methyl]amino}propyl nitrate
• 英文别名: phenyl N-cyano-N'-(3-nitrooxypropyl)carbamimidate
• CAS: 263163-83-3
• 化学式: C₁₁H₁₂N₄O₄
• 分子量: 264.241
• InChiKey: KTNOQILCFSAAIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole dihydrochloride 、 3-{[(cyanoimino)(phenoxy)methyl]amino}propyl nitrate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以54%的产率得到3-{2-cyano-3-[2-({2-[(diaminomethylidene)amino]thiazol-4-yl}methylthio)ethyl]guanidino}propyl nitrate
  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：

  N-氰基羰亚胺二苯基酯 、 3-nitroxypropylammonium nitrate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以87%的产率得到3-{[(cyanoimino)(phenoxy)methyl]amino}propyl nitrate
  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