2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methylpent-4-oxobutanamido)-3-phenylpropanamido)ethyl carbamic acid benzylester | 1563182-68-2

• 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-methylpent-4-oxobutanamido)-3-phenylpropanamido)ethyl carbamic acid benzylester
• CAS: 1563182-68-2
• 化学式: C₃₀H₃₁Cl₂N₃O₅
• 分子量: 584.499
• InChiKey: UOWGZBYBSFFSEG-IGKIAQTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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-methylpent-4-oxobutanamido)-3-phenylpropanamido)ethyl carbamic acid benzylester 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 21.0h， 以60%的产率得到2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylbutanamido)-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：

  3,4-二氯苯乙酸 在 四氧化锇 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 正戊烷 为溶剂， 反应 41.35h， 生成 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-N-methylpent-4-oxobutanamido)-3-phenylpropanamido)ethyl carbamic acid benzylester
  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