2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6'-fluoro-1'-methyl-2'-oxo-1',2'-dihydrospiro[azetidine-3,4'-benzo[d][1,3]oxazine]-1-yl)-N-methylbutanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester | 1563182-89-7

• 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)-4-(6'-fluoro-1'-methyl-2'-oxo-1',2'-dihydrospiro[azetidine-3,4'-benzo[d][1,3]oxazine]-1-yl)-N-methylbutanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester
• CAS: 1563182-89-7
• 化学式: C₄₁H₄₂Cl₂FN₅O₆
• 分子量: 790.719
• InChiKey: FBOHFHUHXLPZLE-PJTQZDKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  55.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  120.52
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6'-fluoro-1'-methyl-2'-oxo-1',2'-dihydrospiro[azetidine-3,4'-benzo[d][1,3]oxazine]-1-yl)-N-methylbutanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.36h， 生成 (R)-N-((S)-1-(2-aminoethylamino)-1-oxo-3-phenylpropan-2-yl)-2-(3,4-dichlorophenyl)-4-(6'-fluoro-1'-methyl-2'-oxo-1',2'-dihydrospiro [azetidine-3,4'-benzo[d][1,3]oxazine]-1-yl)-N-methylbutanamide 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 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 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 67.35h， 生成 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6'-fluoro-1'-methyl-2'-oxo-1',2'-dihydrospiro[azetidine-3,4'-benzo[d][1,3]oxazine]-1-yl)-N-methylbutanamido)-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