[7-(3-tert-Butoxycarbonylamino-propyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-acetic acid ethyl ester | 155309-36-7

• 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: [7-(3-tert-Butoxycarbonylamino-propyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-acetic acid ethyl ester
• CAS: 155309-36-7
• 化学式: C₂₄H₃₃N₃O₆
• 分子量: 459.543
• InChiKey: LEGVKSYRTYFHJU-UHFFFAOYSA-N

物化性质

• 沸点：
  670.7±55.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  [7-(3-tert-Butoxycarbonylamino-propyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-acetic acid ethyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 [7-(3-Amino-propyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-acetic 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
• 作为产物：
  描述：

  6-(N-boc-3-aminopropyl)isatoic acid anhydride 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 吡啶盐酸盐 作用下， 以34%的产率得到[7-(3-tert-Butoxycarbonylamino-propyl)-5,11-dioxo-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-yl]-acetic 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