N-(3-guanidinopropyl)-3-trans-propenamide dinitrate | 140686-29-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-(3-guanidinopropyl)-3-trans-propenamide dinitrate
• 英文别名: N-(3-guanidinopropyl)-3[N'-(3-guanidinopropyl)carbamoyl]-trans-propenamide dinitrate
• CAS: 140686-29-9
• 化学式: C₁₂H₂₄N₈O₂*2HNO₃
• 分子量: 438.401
• InChiKey: ZXZITDAXNRZHMC-BJILWQEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.83
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  245.37
• 氢给体数：
  9.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3,5-二甲基吡唑-1-硝酸咪 、 N-(3-aminopropyl)-3-trans-propenamide 以 水 为溶剂， 反应 8.0h， 生成 N-(3-guanidinopropyl)-3-trans-propenamide dinitrate
  参考文献：
  名称：

  Search for the pharmacophore of the K+ channel blocker, apamin

  摘要：

  The suggestion that the arginine residues, 13Arg and 14Arg, in the octadecapeptide apamin 1 are critically important to its action in blocking Ca2+-dependent K+ channels (and hence part of the 'pharmacophore') has been investigated by examining small peptides containing Arg-Arg or Lys-Arg. Bisguanidine derivatives modelled on the Arg-Arg partial pharmacophore have also been synthesised and tested; in particular, N-(2-guanidinoethyl)-3[N1-(2-guanidinoethyl)carbamoyl]-trans-propenamide 11 and its higher homologue 12. None of the compounds showed more than weak activity (K(i) > 10(-5) M) indicating that although the Arg-Arg fragment may be necessary, it is not a sufficient atom grouping for the pharmacophore.

  DOI：

  10.1016/0223-5234(91)90133-8