(3R)-N-(7-guanidino)heptanoyl-N'-(8-guanidino)octanoyl-3,3-diaminopropionic acid

• 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: (3R)-N-(7-guanidino)heptanoyl-N'-(8-guanidino)octanoyl-3,3-diaminopropionic acid
• 英文别名: (3R)-3-[7-(diaminomethylideneamino)heptanoylamino]-3-[8-(diaminomethylideneamino)octanoylamino]propanoic acid
• 化学式: C₂₀H₄₀N₈O₄
• 分子量: 456.589
• InChiKey: REVXSFNRQSWOJV-OAHLLOKOSA-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：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-氨基辛酸 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 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 、 [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 20.0h， 生成 (3R)-N-(7-guanidino)heptanoyl-N'-(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

文献信息

• US5258398A
  申请人：——

  公开号：US5258398A

  公开（公告）日：1993-11-02
• [EN] ANTITHROMBOTIC DIAMINOALKANOIC ACID DERIVATIVES
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：WO1993011759A1

  公开（公告）日：1993-06-24

  (EN) This invention relates to novel diaminoalkanoic acid derivatives that inhibit platelet aggregation and thrombus formation in mammalian blood thereby being useful in the prevention and treatment of thrombosis associated with disease states such as myocardial infarction, stroke, peripheral arterial disease and disseminated intravascular coagulation, to pharmaceutical compositions including such compounds, and to their use in inhibiting thrombus formation and platelet aggregation in mammals.(FR) L'invention se rapporte à des nouveaux dérivés d'acide diaminoalcanoïque inhibant l'agrégation des plaquettes et la formation de thrombus dans le sang des mammifères et présentant, de ce fait, une efficacité dans la prévention et dans le traitement de thromboses associées à des états pathologiques, tels que l'infarctus du myocarde, l'apoplexie, l'artéréophatie périphérique et la coagulation intravasculaire disseminée. L'invention se rapporte également à des compositions pharmaceutiques comprenant lesdits composés, ainsi qu'à leur utilisation dans l'inhibition de la formation de thrombus et de l'agrégation de plaquettes chez les mammifères.
• Conformationally flexible platelet aggregation inhibitors based on the tetrapeptide Arg-Gly-Asp-Arg
  作者：SI Klein、M Czekaj、BF Molino、V Chu

  DOI：10.1016/s0223-5234(99)80069-5

  日期：1997.10

  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.