(2S,3S)-3-azido-6,6,6-trifluoro-1-phenylhexan-2-amine | 860312-82-9

• 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: (2S,3S)-3-azido-6,6,6-trifluoro-1-phenylhexan-2-amine
• CAS: 860312-82-9
• 化学式: C₁₂H₁₅F₃N₄
• 分子量: 272.273
• InChiKey: KBPALQYUFXBVSA-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azido-6,6,6-trifluoro-1-phenylhexan-2-amine 在 palladium dihydroxide N-羟基-7-氮杂苯并三氮唑 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 生成 N-[(2S,3S)-3-amino-6,6,6-trifluoro-1-phenylhexan-2-yl]-2-[(2-methylcyclopropyl)methylamino]-6-[methyl(methylsulfonyl)amino]pyridine-4-carboxamide
  参考文献：
  名称：

  Discovery and SAR of isonicotinamide BACE-1 inhibitors that bind β-secretase in a N-terminal 10s-loop down conformation

  摘要：

  A series of low-molecular weight 2,6-diamino-isonicotinamide BACE-I inhibitors containing an amine transition-state isostere were synthesized and shown to be highly potent in both enzymatic and cell-based assays. These inhibitors contain a trans-S,S-methyl cyclopropane P-3 which bind BACE-1 in a 10s-loop down conformation giving rise to highly potent compounds with favorable molecular weight and moderate to high susceptibility to P-glycoprotein (P-gp) efflux. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.051
• 作为产物：
  描述：

  BOC-PHE-甲氧基甲胺 在 盐酸 、 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (2S,3S)-3-azido-6,6,6-trifluoro-1-phenylhexan-2-amine
  参考文献：
  名称：

  Discovery and SAR of isonicotinamide BACE-1 inhibitors that bind β-secretase in a N-terminal 10s-loop down conformation

  摘要：

  A series of low-molecular weight 2,6-diamino-isonicotinamide BACE-I inhibitors containing an amine transition-state isostere were synthesized and shown to be highly potent in both enzymatic and cell-based assays. These inhibitors contain a trans-S,S-methyl cyclopropane P-3 which bind BACE-1 in a 10s-loop down conformation giving rise to highly potent compounds with favorable molecular weight and moderate to high susceptibility to P-glycoprotein (P-gp) efflux. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.051

文献信息

• Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of alzheimer's disease
  申请人：Barrow C. James

  公开号：US20070142634A1

  公开（公告）日：2007-06-21

  The present invention is directed to phenylamide and pyridylamide derivative compounds of which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

  本发明涉及苯胺和吡啶胺衍生物化合物，这些化合物是β-分泌酶的抑制剂，并且在治疗涉及β-分泌酶的疾病，如阿尔茨海默病中有用。该发明还涉及包含这些化合物的药物组合物，以及在治疗涉及β-分泌酶的这类疾病中使用这些化合物和组合物。
• US7550481B2
  申请人：——

  公开号：US7550481B2

  公开（公告）日：2009-06-23
• Discovery and SAR of isonicotinamide BACE-1 inhibitors that bind β-secretase in a N-terminal 10s-loop down conformation
  作者：Shaun R. Stauffer、Matthew G. Stanton、Alison R. Gregro、Melissa A. Steinbeiser、Jennifer R. Shaffer、Philippe G. Nantermet、James C. Barrow、Kenneth E. Rittle、Dennis Collusi、Amy S. Espeseth、Ming-Tain Lai、Beth L. Pietrak、M. Katharine Holloway、Georgia B. McGaughey、Sanjeev K. Munshi、Jerome H. Hochman、Adam J. Simon、Harold G. Selnick、Samuel L. Graham、Joseph P. Vacca

  DOI：10.1016/j.bmcl.2006.12.051

  日期：2007.3

  A series of low-molecular weight 2,6-diamino-isonicotinamide BACE-I inhibitors containing an amine transition-state isostere were synthesized and shown to be highly potent in both enzymatic and cell-based assays. These inhibitors contain a trans-S,S-methyl cyclopropane P-3 which bind BACE-1 in a 10s-loop down conformation giving rise to highly potent compounds with favorable molecular weight and moderate to high susceptibility to P-glycoprotein (P-gp) efflux. (c) 2007 Elsevier Ltd. All rights reserved.