ethyl 2-<4-<<2-(tert-butoxycarbonylamino)ethyl>oxy>phenyl>-2-oxoacetate | 150610-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-<4-<<2-(tert-butoxycarbonylamino)ethyl>oxy>phenyl>-2-oxoacetate
• 英文别名: Ethyl 2-[4-(2-Tert-butoxycarbonylaminoethoxy)phenyl]-2-oxoacetate；Ethyl 2-[4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]phenyl]-2-oxoacetate
• CAS: 150610-46-1
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: NGFVEWMOBKXOBS-UHFFFAOYSA-N

物化性质

• 沸点：
  484.7±30.0 °C(predicted)
• 密度：
  1.152±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-<4-<<2-(tert-butoxycarbonylamino)ethyl>oxy>phenyl>-2-oxoacetate 在 palladium on activated charcoal 盐酸 、 氨 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 60.0h， 生成 3-(7-amidino-2-naphthyl)-2-<4-<(2-aminoethyl)oxy>phenyl>propanoic acid
  参考文献：
  名称：

  Molecular model of an interaction between factor Xa and DX-9065a, a novel factor Xa inhibitor: Contribution of the acetimidoylpyrrolidine moiety of the inhibitor to potency and selectivity for serine proteases

  摘要：

  Molecular modeling of a complex between factor Xa (FXa) and DX-9065a, a novel FXa inhibitor, has demonstrated a salt-bridge interaction of the amidinonaphthalene moiety of the inhibitor to the S1 site pocket of the enzyme and a crucial carboxyl group of the inhibitor for the FXa/thrombin selectivity. In the present study, we synthesized some DX-9065a derivatives and studied their interaction modes with FXa, trypsin and thrombin to evaluate the role of the acetimidoylpyrrolidine moiety. The docking study of the inhibitor in the FXa model provided a molecular model of the inhibitor-FXa complex showing a hydrophobic interaction of the pyrrolidine ring with an aryl binding site of FXa, and a hydrogen bond between the acetimidoyl group and the backbone carbonyl oxygen of Glu97. Comparison between the interaction mode of DX-9065a with FXa and those with trypsin and thrombin explained the inhibitory potencies of the enzymes.

  DOI：

  10.1016/0223-5234(96)88248-1
• 作为产物：
  描述：

  2-(4-羟苯基)-2-氧代乙酸乙酯 、 N-(叔丁氧羰基)乙醇胺 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以38.5%的产率得到ethyl 2-<4-<<2-(tert-butoxycarbonylamino)ethyl>oxy>phenyl>-2-oxoacetate
  参考文献：
  名称：

  Molecular model of an interaction between factor Xa and DX-9065a, a novel factor Xa inhibitor: Contribution of the acetimidoylpyrrolidine moiety of the inhibitor to potency and selectivity for serine proteases

  摘要：

  Molecular modeling of a complex between factor Xa (FXa) and DX-9065a, a novel FXa inhibitor, has demonstrated a salt-bridge interaction of the amidinonaphthalene moiety of the inhibitor to the S1 site pocket of the enzyme and a crucial carboxyl group of the inhibitor for the FXa/thrombin selectivity. In the present study, we synthesized some DX-9065a derivatives and studied their interaction modes with FXa, trypsin and thrombin to evaluate the role of the acetimidoylpyrrolidine moiety. The docking study of the inhibitor in the FXa model provided a molecular model of the inhibitor-FXa complex showing a hydrophobic interaction of the pyrrolidine ring with an aryl binding site of FXa, and a hydrogen bond between the acetimidoyl group and the backbone carbonyl oxygen of Glu97. Comparison between the interaction mode of DX-9065a with FXa and those with trypsin and thrombin explained the inhibitory potencies of the enzymes.

  DOI：

  10.1016/0223-5234(96)88248-1

文献信息

• Aromatic amidine derivatives and salts thereof
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0540051B1

  公开（公告）日：1996-04-03
• US5576343A
  申请人：——

  公开号：US5576343A

  公开（公告）日：1996-11-19
• US5620991A
  申请人：——

  公开号：US5620991A

  公开（公告）日：1997-04-15
• US5866577A
  申请人：——

  公开号：US5866577A

  公开（公告）日：1999-02-02
• US5962695A
  申请人：——

  公开号：US5962695A

  公开（公告）日：1999-10-05