(S)-ethyl 1-(4-((3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl)amino)phenyl)piperidine-4-carboxylate | 1444001-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-ethyl 1-(4-((3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl)amino)phenyl)piperidine-4-carboxylate
• 英文别名: ethyl 1-[4-[[(2S)-3-(1,3-dioxoisoindol-2-yl)-2-hydroxypropyl]amino]phenyl]piperidine-4-carboxylate
• CAS: 1444001-02-8
• 化学式: C₂₅H₂₉N₃O₅
• 分子量: 451.522
• InChiKey: AWKSUFFENGXVEH-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 1-(4-((3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl)amino)phenyl)piperidine-4-carboxylate 在 4-二甲氨基吡啶 、 三乙酰氧基硼氢化钠 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 (S)-ethyl 1-(4-(2-oxo-5-(((4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzyl)amino)methyl)oxazolidin-3-yl)phenyl)piperidine-4-carboxylate
  参考文献：
  名称：

  Low molecular weight dual inhibitors of factor Xa and fibrinogen binding to GPIIb/IIIa with highly overlapped pharmacophores

  摘要：

  Dual antithrombotic agents acting as anticoagulants and aggregation inhibitors could have substantial advantages over currently prescribed combinations of antithrombotic drugs. Herein, we report compounds with moderate inhibitory activity for factor Xa and fibrinogen GPIIb/IIIa binding (both in the micromolar range). These compounds resulted from our efforts to merge the pharmacophores of selective factor Xa inhibitor rivaroxaban with a mimic of the Arg-Gly-Asp (RGD) sequence of fibrinogen to obtain designed multiple ligands with potential antithrombotic activity. Resulting from this study, a structurally novel class of submicromolar fibrinogen GPIIb/IIIa binding inhibitor bearing 1,2,4-oxadiazol-5(4H)-one moiety is also described. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.056
• 作为产物：
  描述：

  对氟硝基苯 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 20.0~55.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 (S)-ethyl 1-(4-((3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl)amino)phenyl)piperidine-4-carboxylate
  参考文献：
  名称：

  Low molecular weight dual inhibitors of factor Xa and fibrinogen binding to GPIIb/IIIa with highly overlapped pharmacophores

  摘要：

  Dual antithrombotic agents acting as anticoagulants and aggregation inhibitors could have substantial advantages over currently prescribed combinations of antithrombotic drugs. Herein, we report compounds with moderate inhibitory activity for factor Xa and fibrinogen GPIIb/IIIa binding (both in the micromolar range). These compounds resulted from our efforts to merge the pharmacophores of selective factor Xa inhibitor rivaroxaban with a mimic of the Arg-Gly-Asp (RGD) sequence of fibrinogen to obtain designed multiple ligands with potential antithrombotic activity. Resulting from this study, a structurally novel class of submicromolar fibrinogen GPIIb/IIIa binding inhibitor bearing 1,2,4-oxadiazol-5(4H)-one moiety is also described. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.056