3-[2-(4-Chloro-benzylamino)-5-iodo-benzoylamino]-propionic acid ethyl ester | 151978-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[2-(4-Chloro-benzylamino)-5-iodo-benzoylamino]-propionic acid ethyl ester
• 英文别名: Ethyl 3-[[2-[(4-chlorophenyl)methylamino]-5-iodobenzoyl]amino]propanoate
• CAS: 151978-68-6
• 化学式: C₁₉H₂₀ClIN₂O₃
• 分子量: 486.737
• InChiKey: IAXRELZATIEBCX-UHFFFAOYSA-N

物化性质

• 沸点：
  562.8±50.0 °C(predicted)
• 密度：
  1.552±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(4-Chloro-benzylamino)-5-iodo-benzoylamino]-propionic acid ethyl ester 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 乙酸酐 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成
  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-碘-2H-3,1-苯并噁嗪-2,4(1H)-二酮 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-(4-Chloro-benzylamino)-5-iodo-benzoylamino]-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

文献信息

• Mono-N-alkylation of anthranilamides via quinazolinones. An efficient synthesis of G5598, a benzodiazepine dione gpIIbIIIa antagonist
  作者：Robert R Webb、Peter L Barker、Mark Baier、Mark E Reynolds、Kirk D Robarge、Brent K Blackburn、Maureen H Tischler、Kenneth J Weese

  DOI：10.1016/s0040-4039(00)76773-6

  日期：1994.4

  The mono-N-alkylation of an anthranilamide derivative via the reductive ring opening of a quinazolinone precursor, enables the synthesis of benzodiazepine dione derivative G5598, a potent inhibitor of the in vitro binding of GpIIbIIIa to fibrinogen.
• Webb Robert R., Barker Peter L., Baier Mark, Reynolds Mark E., RobargeKir+, Tetrahedron Lett., 35 (1994) N 14, S 2113-2116
  作者：Webb Robert R., Barker Peter L., Baier Mark, Reynolds Mark E., RobargeKir+

  DOI：——

  日期：——