3-[7-(3-tert-Butoxycarbonylamino-propyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-propionic acid ethyl ester | 155309-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 3-[7-(3-tert-Butoxycarbonylamino-propyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-propionic acid ethyl ester
• CAS: 155309-41-4
• 化学式: C₂₂H₃₁N₃O₆
• 分子量: 433.505
• InChiKey: ZSZOOWMFMHWTIW-UHFFFAOYSA-N

物化性质

• 沸点：
  648.8±55.0 °C(predicted)
• 密度：
  1.175±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[7-(3-tert-Butoxycarbonylamino-propyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-propionic acid ethyl ester 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 3-[7-(3-Amino-propyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-propionic acid
  参考文献：
  名称：

  From Peptide to Non-Peptide. 2. The de Novo Design of Potent, Non-peptidal Inhibitors of Platelet Aggregation Based on a Benzodiazepinedione Scaffold

  摘要：

  Earlier studies of peptides containing the arginine-glycine-aspartic acid (RGD) sequence led to the development of a structural model describing the three-dimensional presentation required for RGD-mediated inhibition of glycoprotein IIbIIIa/fibrinogen binding. We describe here the use of that structural model to design a rigid, non-peptidal lead series that reproduces the topography of the peptide backbone using a benzodiazepinedione scaffold. This scaffold is used to synthesize novel molecules which are highly potent inhibitors of platelet aggregation and which possess improved bioavailability. The importance of shape as a design criterion is demonstrated by constructing molecules that present alternative topographies; these molecules are shown to be significantly less potent.

  DOI：

  10.1021/ja00091a008
• 作为产物：
  描述：

  3-(Carboxymethyl-amino)-propionic acid ethyl ester 、 6-(N-boc-3-aminopropyl)isatoic acid anhydride 在 吡啶 、 吡啶盐酸盐 作用下， 以6%的产率得到3-[7-(3-tert-Butoxycarbonylamino-propyl)-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-propionic acid ethyl ester
  参考文献：
  名称：

  From Peptide to Non-Peptide. 2. The de Novo Design of Potent, Non-peptidal Inhibitors of Platelet Aggregation Based on a Benzodiazepinedione Scaffold

  摘要：

  Earlier studies of peptides containing the arginine-glycine-aspartic acid (RGD) sequence led to the development of a structural model describing the three-dimensional presentation required for RGD-mediated inhibition of glycoprotein IIbIIIa/fibrinogen binding. We describe here the use of that structural model to design a rigid, non-peptidal lead series that reproduces the topography of the peptide backbone using a benzodiazepinedione scaffold. This scaffold is used to synthesize novel molecules which are highly potent inhibitors of platelet aggregation and which possess improved bioavailability. The importance of shape as a design criterion is demonstrated by constructing molecules that present alternative topographies; these molecules are shown to be significantly less potent.

  DOI：

  10.1021/ja00091a008