N,N-dioctyl-O-tert-butyltyrosylglycylglycylphenylalanylleucine methyl ester | 107941-93-5

• 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: N,N-dioctyl-O-tert-butyltyrosylglycylglycylphenylalanylleucine methyl ester
• CAS: 107941-93-5
• 化学式: C₄₉H₇₉N₅O₇
• 分子量: 850.196
• InChiKey: FICKLXTWPZTTBX-SVWSIEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  61.0
• 可旋转键数：
  31.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  155.17
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N,N-dioctyl-O-tert-butyltyrosylglycylglycylphenylalanylleucine methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 以67.2%的产率得到(S)-2-[(S)-2-(2-{2-[(S)-3-(4-tert-Butoxy-phenyl)-2-dioctylamino-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
  参考文献：
  名称：

  N,N-Dialkylated leucine enkephalins as potential .delta. opioid receptor antagonists

  摘要：

  A series of N,N-dialkylated leucine enkephalins were prepared in order to study the effect of substitution on antagonist activity at the delta opioid receptor. The target peptides 1-7 were evaluated in the mouse vas deferens (MVD) and guinea pig ileum (GPI) at 1 microM. All of the compounds except [N,N-di-2-phenethyl,Leu5]enkephalin (7) showed antagonist activity in the MVD against the delta receptor agonist [D-Ala2,D-Leu5]enkephalin. The most potent congener, [N,N-dibenzyl,Leu5]enkephalin (3), was 2.5-fold more potent than [N,N-diallyl,Leu5]enkephalin (1). None of the compounds at 1 microM showed any antagonist activity against agonists for other receptor types. The N,N-di-2-phenethyl (7) and N,N-dioctyl (6) analogues showed significant agonist activity at 1 microM in the MVD.

  DOI：

  10.1021/jm00390a005
• 作为产物：
  描述：

  L-亮氨酸甲酯盐酸盐 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 ammonium formate 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.67h， 生成 N,N-dioctyl-O-tert-butyltyrosylglycylglycylphenylalanylleucine methyl ester
  参考文献：
  名称：

  N,N-Dialkylated leucine enkephalins as potential .delta. opioid receptor antagonists

  摘要：

  A series of N,N-dialkylated leucine enkephalins were prepared in order to study the effect of substitution on antagonist activity at the delta opioid receptor. The target peptides 1-7 were evaluated in the mouse vas deferens (MVD) and guinea pig ileum (GPI) at 1 microM. All of the compounds except [N,N-di-2-phenethyl,Leu5]enkephalin (7) showed antagonist activity in the MVD against the delta receptor agonist [D-Ala2,D-Leu5]enkephalin. The most potent congener, [N,N-dibenzyl,Leu5]enkephalin (3), was 2.5-fold more potent than [N,N-diallyl,Leu5]enkephalin (1). None of the compounds at 1 microM showed any antagonist activity against agonists for other receptor types. The N,N-di-2-phenethyl (7) and N,N-dioctyl (6) analogues showed significant agonist activity at 1 microM in the MVD.

  DOI：

  10.1021/jm00390a005