(S)-1-(4-methanesulfonamidophenoxy)-3-(N-(2-butyroxyethyl)-3,4-dichlorophenylethylamino)-2-propanol | 457898-07-6

• 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: (S)-1-(4-methanesulfonamidophenoxy)-3-(N-(2-butyroxyethyl)-3,4-dichlorophenylethylamino)-2-propanol
• 英文别名: 2-[2-(3,4-dichlorophenyl)ethyl-[(2S)-2-hydroxy-3-[4-(methanesulfonamido)phenoxy]propyl]amino]ethyl butanoate
• CAS: 457898-07-6
• 化学式: C₂₄H₃₂Cl₂N₂O₆S
• 分子量: 547.5
• InChiKey: CLASKYWJDPEUGM-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-methanesulfonamidophenoxy)-3-(N-(2-butyroxyethyl)-3,4-dichlorophenylethylamino)-2-propanol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以75%的产率得到(S)-1-(4-methanesulfonamidophenoxy)-3-(N-(2-hydroxyethyl)-3,4-dichlorophenylethylamino)-2-propanol
  参考文献：
  名称：

  Enantiomeric Propanolamines as selective N-Methyl-d-aspartate 2B Receptor Antagonists

  摘要：

  Enantiomeric propanolamines have been identified as a new class of NR2B-selective NMDA receptor antagonists. The most effective agents are biaryl structures, synthesized in six steps with overall yields ranging from 11-64%. The compounds are potent and selective inhibitors of NR2B-containing recombinant NMDA receptors with IC50 values between 30-100 nM. Potency is strongly controlled by substitution on both rings and the centrally located amine nitrogen. SAR analysis suggests that well-balanced polarity and chain-length factors provide the greatest inhibitory potency. Structural comparisons based on 3D shape analysis and electrostatic complementarity support this conclusion. The antagonists are neuroprotective in both in vitro and in vivo models of ischemic cell death. In addition, some compounds exhibit anticonvulsant properties. Unlike earlier generation NMDA receptor antagonists and some NR2B-selective antagonists, the present series of propanolamines does not cause increased locomotion in rodents. Thus, the NR2B-selective antagonists exhibit a range of therapeutically interesting properties.

  DOI：

  10.1021/jm8002153
• 作为产物：
  描述：

  (S)-1-(4-methanesulfonamidophenoxy)-3-(3,4-dichlorophenylethylamino)-2-propanol 、 2-oxoethyl butyrate 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 以85%的产率得到(S)-1-(4-methanesulfonamidophenoxy)-3-(N-(2-butyroxyethyl)-3,4-dichlorophenylethylamino)-2-propanol
  参考文献：
  名称：

  Enantiomeric Propanolamines as selective N-Methyl-d-aspartate 2B Receptor Antagonists

  摘要：

  Enantiomeric propanolamines have been identified as a new class of NR2B-selective NMDA receptor antagonists. The most effective agents are biaryl structures, synthesized in six steps with overall yields ranging from 11-64%. The compounds are potent and selective inhibitors of NR2B-containing recombinant NMDA receptors with IC50 values between 30-100 nM. Potency is strongly controlled by substitution on both rings and the centrally located amine nitrogen. SAR analysis suggests that well-balanced polarity and chain-length factors provide the greatest inhibitory potency. Structural comparisons based on 3D shape analysis and electrostatic complementarity support this conclusion. The antagonists are neuroprotective in both in vitro and in vivo models of ischemic cell death. In addition, some compounds exhibit anticonvulsant properties. Unlike earlier generation NMDA receptor antagonists and some NR2B-selective antagonists, the present series of propanolamines does not cause increased locomotion in rodents. Thus, the NR2B-selective antagonists exhibit a range of therapeutically interesting properties.

  DOI：

  10.1021/jm8002153