N¹-acetyl-N⁴-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-5(4-tert-butoxycarbonylamino-phenyl)-1,4-pentane diamine | 119860-11-6

• 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: N¹-acetyl-N⁴-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-5(4-tert-butoxycarbonylamino-phenyl)-1,4-pentane diamine
• 英文别名: benzyl N-[5-acetamido-4,4-difluoro-3-hydroxy-1-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]pentan-2-yl]carbamate
• CAS: 119860-11-6
• 化学式: C₂₆H₃₃F₂N₃O₆
• 分子量: 521.561
• InChiKey: BJOBZKNIFNMTRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N¹-acetyl-N⁴-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-5(4-tert-butoxycarbonylamino-phenyl)-1,4-pentane diamine 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (N-benzyloxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-3,3-difluoro-2-hydroxy-1-<4((((benzyloxycarbonylamino)benzyloxycarbonylimino)methyl)amino)phenyl>methyl>butyl-L-prolinamide
  参考文献：
  名称：

  General synthesis of polyfunctionalized fluoromethyleneketone retroamides as potential inhibitors of thrombin

  摘要：

  Synthesis of polyfunctionalyzed fluoromethyleneketone retroamides is described. A potential inhibitor of human Thrombin has been prepared through a Reformatsky type condensation from N-protected p.NO2 phenylalaninal. The reaction conditions are applicable to a variety of NO2 substituted aldehydes.

  DOI：

  10.1016/0040-4039(91)80491-n
• 作为产物：
  描述：

  N¹-acetyl-N⁴-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-nitrophenyl)-1,4-pentanediamine 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 N¹-acetyl-N⁴-benzyloxycarbonyl-2,2-difluoro-3-hydroxy-5(4-tert-butoxycarbonylamino-phenyl)-1,4-pentane diamine
  参考文献：
  名称：

  General synthesis of polyfunctionalized fluoromethyleneketone retroamides as potential inhibitors of thrombin

  摘要：

  Synthesis of polyfunctionalyzed fluoromethyleneketone retroamides is described. A potential inhibitor of human Thrombin has been prepared through a Reformatsky type condensation from N-protected p.NO2 phenylalaninal. The reaction conditions are applicable to a variety of NO2 substituted aldehydes.

  DOI：

  10.1016/0040-4039(91)80491-n

文献信息

• Novel peptidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0356595A1

  公开（公告）日：1990-03-07

  This invention relates to analogs of peptidase substrates in which the nitrogen atom of the scissile amide bond of a partial retropeptide analog of the substrate has been replaced by a difluoromethylene moiety. These peptidase substrate analogs provide specific enzyme inhibitors for a variety of proteases, the inhibition of which exert valuable pharmacological activities and therefore have useful physiological consequences in a variety of disease states.

  这项发明涉及肽酶底物的类似物，其中底物的部分反肽类似物的可切割酰胺键的氮原子被二氟甲亚甲基取代。这些肽酶底物类似物提供了各种蛋白酶的特异性酶抑制剂，这些蛋白酶的抑制对多种蛋白酶具有有用的药理活性，因此在多种疾病状态下具有有用的生理后果。
• Difluoromethyleneketone retroamide, a versatile concept of inactivation of proteolytic enzymes
  作者：D. Schirlin、S. Baltzer、J.M. Altenburger、C. Tarnus、J.M. Remy

  DOI：10.1016/0040-4020(95)00896-g

  日期：1996.1

  The synthesis of difluoromethyleneketone retroamides is described. Several examples of application to aspartyl or seryl proteases illustrate the versatility of this inactivation concept.
• General synthesis of polyfunctionalized fluoromethyleneketone retroamides as potential inhibitors of thrombin
  作者：J.M. Altenburger、D. Schirlin

  DOI：10.1016/0040-4039(91)80491-n

  日期：1991.12

  Synthesis of polyfunctionalyzed fluoromethyleneketone retroamides is described. A potential inhibitor of human Thrombin has been prepared through a Reformatsky type condensation from N-protected p.NO2 phenylalaninal. The reaction conditions are applicable to a variety of NO2 substituted aldehydes.