2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester | 1563182-82-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester
• CAS: 1563182-82-0
• 化学式: C₃₁H₃₃Cl₂N₃O₅
• 分子量: 598.526
• InChiKey: RPQLKDJXIWIDPW-LSYYVWMOSA-N

物化性质

• 沸点：
  818.1±65.0 °C(predicted)
• 密度：
  1.272±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104.81
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-fluoro-1-methylspiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one 、 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以71%的产率得到2-((S)-2-((S)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester
  参考文献：
  名称：

  Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists

  摘要：

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.

  DOI：

  10.1021/ml400528y
• 作为产物：
  描述：

  2-((S)-2-((S)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester
  参考文献：
  名称：

  Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists

  摘要：

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.

  DOI：

  10.1021/ml400528y