5-Bromo-2-methoxymandelic acid | 863562-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Bromo-2-methoxymandelic acid
• 英文别名: 2-(5-bromo-2-methoxyphenyl)-2-hydroxyacetic acid
• CAS: 863562-53-2
• 化学式: C₉H₉BrO₄
• 分子量: 261.072
• InChiKey: POORACPHOZSRDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-methoxymandelic acid 、 Fmoc-L-缬氨酸 、 苄硫醇 、 tert-butyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate 生成 (3S)-5-(benzylsulfanyl)-3-[(2S)-2-[2-(5-bromo-2-methoxyphenyl)-2-hydroxyacetamido]-3-methylbutanamido]-4-oxopentanoic acid
  参考文献：
  名称：

  Lipophilic versus hydrogen-bonding effect in P3 on potency and selectivity of valine aspartyl ketones as caspase 3 inhibitors

  摘要：

  Caspase 3 is a cysteinyl protease that mediates apoptotic cell death. Its inhibition may have an important impact in the treatment of several degenerative diseases. The P, aspartic acid residue is a required element of recognition for this enzyme that was maintained constant along with the adjacent natural valine as the P-2 group. The thiobenzylmethylketone warhead on the aspartate was conveniently handled through solid-phase synthesis allowing modification in the P-3 region that eventually led to simpler derivatives with increased potency against caspase 3. The key to such an effect is the introduction of hydroxyl group alpha to the P3 carbonyl. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.116
• 作为产物：
  描述：

  ethyl 2-(5-bromo-2-methoxyphenyl)-2-oxoacetate 在 lithium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Bromo-2-methoxymandelic acid
  参考文献：
  名称：

  Lipophilic versus hydrogen-bonding effect in P3 on potency and selectivity of valine aspartyl ketones as caspase 3 inhibitors

  摘要：

  Caspase 3 is a cysteinyl protease that mediates apoptotic cell death. Its inhibition may have an important impact in the treatment of several degenerative diseases. The P, aspartic acid residue is a required element of recognition for this enzyme that was maintained constant along with the adjacent natural valine as the P-2 group. The thiobenzylmethylketone warhead on the aspartate was conveniently handled through solid-phase synthesis allowing modification in the P-3 region that eventually led to simpler derivatives with increased potency against caspase 3. The key to such an effect is the introduction of hydroxyl group alpha to the P3 carbonyl. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.116