2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester | 1563182-79-5

• 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-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester
• CAS: 1563182-79-5
• 化学式: C₃₁H₃₅Cl₂N₃O₅
• 分子量: 600.542
• InChiKey: OYEYOKMCKXPSBZ-NAKRPHOHSA-N

物化性质

• 沸点：
  820.6±65.0 °C(predicted)
• 密度：
  1.276±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 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：
  0.32
• 拓扑面积：
  107.97
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 48.36h， 生成 (R)-N-((S)-1-(2-aminoethylamino)-1-oxo-3-phenylpropan-2-yl)-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-methylpentanamide dihydrochloride
  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 Wilkinson's catalyst 、 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 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 37.85h， 生成 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-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