(2S)-2-(4-bromophenyl)propanamide | 1217864-24-8

• 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)-2-(4-bromophenyl)propanamide
• CAS: 1217864-24-8
• 化学式: C₉H₁₀BrNO
• 分子量: 228.088
• InChiKey: ZWRSIOSZQWOKPB-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)amino)pentanamide 、 (2S)-2-(4-bromophenyl)propanamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 生成 N²-((1S)-1-{4'-[(1S)-2-amino-1-methyl-2-oxoethyl]biphenyl-4-yl}-2,2,2-trifluoroethyl)-N¹-(1-cyanocyclopropyl)-4-fluoro-L-leucinamide
  参考文献：
  名称：

  The discovery of MK-0674, an orally bioavailable cathepsin K inhibitor

  摘要：

  MK-0674 is a potent and selective cathepsin K inhibitor from the same structural class as odanacatib with a comparable inhibitory potency pro. le against Cat K. It is orally bioavailable and exhibits long half-life in pre-clinical species. In vivo studies using deuterated MK-0674 show stereoselective epimerization of the alcohol stereocenter via an oxidation/reduction cycle. From in vitro incubations, two metabolites could be identified: the hydroxyleucine and the glucuronide conjugate which were confirmed using authentic synthetic standards. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.12.083
• 作为产物：
  描述：

  (S)-2-(4-bromophenyl)propanoic acid 在 氯化铵 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以90%的产率得到(2S)-2-(4-bromophenyl)propanamide
  参考文献：
  名称：

  The discovery of MK-0674, an orally bioavailable cathepsin K inhibitor

  摘要：

  MK-0674 is a potent and selective cathepsin K inhibitor from the same structural class as odanacatib with a comparable inhibitory potency pro. le against Cat K. It is orally bioavailable and exhibits long half-life in pre-clinical species. In vivo studies using deuterated MK-0674 show stereoselective epimerization of the alcohol stereocenter via an oxidation/reduction cycle. From in vitro incubations, two metabolites could be identified: the hydroxyleucine and the glucuronide conjugate which were confirmed using authentic synthetic standards. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.12.083