L-2-methyl-4-N-benzoylpentaphenone | 191104-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-2-methyl-4-N-benzoylpentaphenone
• 英文别名: N-[(2S)-4-methyl-1-oxo-1-phenylpentan-2-yl]benzamide
• CAS: 191104-42-4
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: QWLDIFWLWQHFPW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-2-methyl-4-N-benzoylpentaphenone 在 盐酸 作用下， 以 甲醇 为溶剂， 以95%的产率得到2-氨基苯乙酮盐酸盐
  参考文献：
  名称：

  Pyrrolomorphinans as δ Opioid Receptor Antagonists. The Role of Steric Hindrance in Conferring Selectivity

  摘要：

  A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at mu and kappa receptors in promoting delta opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K-e values in the range 2-15 nM and were delta selective. Since the unsubstituted analogue 4 possessed delta antagonist potency of similar magnitude, but was not delta selective, it is suggested that the 2',3'-substitution confers delta selectivity by hindering the interaction of the pharmacophore at mu and kappa receptors, while not affecting delta receptors.

  DOI：

  10.1021/jm970189y
• 作为产物：
  描述：

  N-苯甲酰-L-亮氨酸 、 苯基溴化镁 在 正丁基锂 作用下， 以 四氢呋喃 、 甲酸 、 正己烷 为溶剂， 以20%的产率得到L-2-methyl-4-N-benzoylpentaphenone
  参考文献：
  名称：

  Pyrrolomorphinans as δ Opioid Receptor Antagonists. The Role of Steric Hindrance in Conferring Selectivity

  摘要：

  A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at mu and kappa receptors in promoting delta opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K-e values in the range 2-15 nM and were delta selective. Since the unsubstituted analogue 4 possessed delta antagonist potency of similar magnitude, but was not delta selective, it is suggested that the 2',3'-substitution confers delta selectivity by hindering the interaction of the pharmacophore at mu and kappa receptors, while not affecting delta receptors.

  DOI：

  10.1021/jm970189y

文献信息

• Pyrrolomorphinans as δ Opioid Receptor Antagonists. The Role of Steric Hindrance in Conferring Selectivity
  作者：F. Farouz-Grant、P. S. Portoghese

  DOI：10.1021/jm970189y

  日期：1997.6.1

  A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at mu and kappa receptors in promoting delta opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K-e values in the range 2-15 nM and were delta selective. Since the unsubstituted analogue 4 possessed delta antagonist potency of similar magnitude, but was not delta selective, it is suggested that the 2',3'-substitution confers delta selectivity by hindering the interaction of the pharmacophore at mu and kappa receptors, while not affecting delta receptors.