ethyl (1R,2S,3S,4R,6R)-2-amino-6-[3-(4-aminoanilino)phenyl]-3-phenylsulfanylbicyclo[2.2.1]heptane-2-carboxylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (1R,2S,3S,4R,6R)-2-amino-6-[3-(4-aminoanilino)phenyl]-3-phenylsulfanylbicyclo[2.2.1]heptane-2-carboxylate
• 化学式: C₂₈H₃₁N₃O₂S
• 分子量: 473.639
• InChiKey: UNERZHAOJDVDOW-QJVYPZHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1RS,2SR,3SR,4RS,6RS)-ethyl 2-amino-6-(3-((4-nitrophenyl)amino)phenyl)-3-(phenylthio)bicyclo[2.2.1]heptane-2-carboxylate 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到ethyl (1R,2S,3S,4R,6R)-2-amino-6-[3-(4-aminoanilino)phenyl]-3-phenylsulfanylbicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  2-Amino-3-(phenylsulfanyl)norbornane-2-carboxylate: An Appealing Scaffold for the Design of Rac1–Tiam1 Protein–Protein Interaction Inhibitors

  摘要：

  The use of the 2-amino-3-(phenylsulfany1)norbornane-2-carboxylate scaffold has been exploited for the de novo design of potent Rac1 inhibitors acting as modulators of the protein protein interaction between Rac1 and Tiam1. A series of compounds differing in regio- and stereochemistry has been prepared by way of a multistep synthesis based on cycloaddition reactions and Pd chemistry. Pharmacological analyses showed that all the prepared compounds were active and selective for Rac1, and the most effective compound 13 was capable of inhibiting smooth muscle cell migration. The synthesis of this derivative was successfully scaled up to 1 g.

  DOI：

  10.1021/jm401924s