Ethyl (N-{4-[(1-Acetimidoyl-4-piperidyl)oxy]phenyl}-N-[(7-amidino-2-naphthyl)methyl]sulfamoyl)acetate | 364614-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Ethyl (N-{4-[(1-Acetimidoyl-4-piperidyl)oxy]phenyl}-N-[(7-amidino-2-naphthyl)methyl]sulfamoyl)acetate
• 英文别名: ((7-Carbamimidoyl-naphthalen-2-ylmethyl)-{4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenyl}-sulfamoyl)-acetic acid ethyl ester；ethyl 2-[(7-carbamimidoylnaphthalen-2-yl)methyl-[4-(1-ethanimidoylpiperidin-4-yl)oxyphenyl]sulfamoyl]acetate
• CAS: 364614-52-8
• 化学式: C₂₉H₃₅N₅O₅S
• 分子量: 565.693
• InChiKey: CSHXIHWIECFVRC-UHFFFAOYSA-N

物化性质

• 沸点：
  741.3±70.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl (N-{4-[(1-Acetimidoyl-4-piperidyl)oxy]phenyl}-N-[(7-amidino-2-naphthyl)methyl]sulfamoyl)acetate 在 盐酸 作用下， 生成 ((7-carbamimidoyl-naphthalen-2-ylmethyl)-{4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenyl}-sulfamoyl)-acetic acid
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  7-({4-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]anilino}methyl)naphthalene-2-carbonitrile 在 吡啶 、 羟胺 、 乙酸酐 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 Ethyl (N-{4-[(1-Acetimidoyl-4-piperidyl)oxy]phenyl}-N-[(7-amidino-2-naphthyl)methyl]sulfamoyl)acetate
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7

文献信息

• Bioorg. Med. Chem. 2002, 10, 1509-1523
  作者：

  DOI：——

  日期：——
• Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors
  作者：Wenrong Huang、Penglie Zhang、Jingmei F Zuckett、Lingyan Wang、John Woolfrey、Yonghong Song、Zhaozhong J Jia、Lane A Clizbe、Ting Su、Katherine Tran、Brian Huang、Paul Wong、Uma Sinha、Gary Park、Andrea Reed、John Malinowski、Stanley J Hollenbach、Robert M Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00927-7

  日期：2003.2

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.