N-α-[8-(nitroguanidino)octanoyl]aspartic acid amide β-benzyl ester | 150638-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-α-[8-(nitroguanidino)octanoyl]aspartic acid amide β-benzyl ester
• 英文别名: benzyl (3S)-4-amino-3-[8-[[(E)-N'-nitrocarbamimidoyl]amino]octanoylamino]-4-oxobutanoate
• CAS: 150638-21-4
• 化学式: C₂₀H₃₀N₆O₆
• 分子量: 450.495
• InChiKey: SLAMZUCFWRWKDT-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-α-[8-(nitroguanidino)octanoyl]aspartic acid amide β-benzyl ester 在 palladium on activated charcoal 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 25.0 ℃ 、379.21 kPa 条件下， 反应 19.0h， 生成 N,N'-bis-(8-guanidino)octanoyl-3,3-diaminopropionic acid
  参考文献：
  名称：

  Conformationally flexible platelet aggregation inhibitors based on the tetrapeptide Arg-Gly-Asp-Arg

  摘要：

  A series of nonpeptide fibrinogen receptor antagonists based upon the tetrapeptide Arg-Gly-Asp-Arg were prepared. These relatively simple derivatives incorporate a high degree of conformational flexibility that was anticipated to allow them to attain the requisite conformation for binding to the platelet fibrinogen receptor. Optimization of the distances between the required acidic and basic functional groups led eventually to compound 7, which is a one hundred-fold more potent inhibitor of platelet aggregation than the peptide it is based upon.

  DOI：

  10.1016/s0223-5234(99)80069-5
• 作为产物：
  描述：

  8-氨基辛酸 在 硫酸 、 硝酸 、 potassium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-α-[8-(nitroguanidino)octanoyl]aspartic acid amide β-benzyl ester
  参考文献：
  名称：

  Conformationally flexible platelet aggregation inhibitors based on the tetrapeptide Arg-Gly-Asp-Arg

  摘要：

  A series of nonpeptide fibrinogen receptor antagonists based upon the tetrapeptide Arg-Gly-Asp-Arg were prepared. These relatively simple derivatives incorporate a high degree of conformational flexibility that was anticipated to allow them to attain the requisite conformation for binding to the platelet fibrinogen receptor. Optimization of the distances between the required acidic and basic functional groups led eventually to compound 7, which is a one hundred-fold more potent inhibitor of platelet aggregation than the peptide it is based upon.

  DOI：

  10.1016/s0223-5234(99)80069-5