2-(R)-<<(tert-butyloxy)carbonyl>amino>-6-(3-o-tolylureido)hexanoic acid | 166898-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(R)-<<(tert-butyloxy)carbonyl>amino>-6-(3-o-tolylureido)hexanoic acid
• 英文别名: (2R)-6-[(2-methylphenyl)carbamoylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 166898-11-9
• 化学式: C₁₉H₂₉N₃O₅
• 分子量: 379.456
• InChiKey: MZOODEATOYXMNR-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(R)-<<(tert-butyloxy)carbonyl>amino>-6-(3-o-tolylureido)hexanoic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 64.75h， 生成 2-<<(adamantan-2-yloxy)carbonyl>amino>-N-<2-(R)-<<(tert-butyloxy)carbonyl>amino>-6-(3-o-tolylureido)hexyl>-3-(1H-indol-3-yl)-2-(R)-methylpropionamide
  参考文献：
  名称：

  Modification of Receptor Selectivity and Functional Activity in Cholecystokinin Peptoid Ligands

  摘要：

  Hybrid analogs of the cholecystokinin A (CCK-A) receptor selective tetrapeptide agonist Boc-Trp-Lys(Tac)-Asp-MePhe-NH2 (1, A-71623) and the CCK-B receptor selective antagonists PD-135118 (2) and CI-988 (3) were prepared. Incorporation of the Lys(Tac) side chain into 2 produced a moderately potent antagonist of CCK-8 in the isolated guinea pig gallbladder (GPGB). Incorporation of the Lys(Tac) side chain into 3 produced the novel agonist analog 7 (EC(50) = 28 nM in the GPGB) with excellent affinity for both human CCK-A (IC50 = 12 nM) and CCK-B (IC50 = 17 nM) receptors. Analog 7 was a full agonist (EC(50) = 3.5 nM) for calcium mobilization on CHO-K1 cells expressing hCCK-A receptors but a partial agonist on CHO-K1 cells expressing hCCK-B receptors, eliciting a weak agonist reponse (EC(50) = 2800 nM) and antagonizing CCK-8-induced calcium mobilization (K-B = 20 nM). Despite this unusual in vitro profile, analog 7 was a potent anorectic agent in rats (ED(50) = 30 nmol/kg) following intraperitoneal administration.

  DOI：

  10.1021/jm00017a022
• 作为产物：
  描述：

  N-(叔丁氧羰基)-D-赖氨酸 、 邻甲苯异氰酸酯 在 sodium hydroxide 作用下， 反应 15.0h， 以100%的产率得到2-(R)-<<(tert-butyloxy)carbonyl>amino>-6-(3-o-tolylureido)hexanoic acid
  参考文献：
  名称：

  Modification of Receptor Selectivity and Functional Activity in Cholecystokinin Peptoid Ligands

  摘要：

  Hybrid analogs of the cholecystokinin A (CCK-A) receptor selective tetrapeptide agonist Boc-Trp-Lys(Tac)-Asp-MePhe-NH2 (1, A-71623) and the CCK-B receptor selective antagonists PD-135118 (2) and CI-988 (3) were prepared. Incorporation of the Lys(Tac) side chain into 2 produced a moderately potent antagonist of CCK-8 in the isolated guinea pig gallbladder (GPGB). Incorporation of the Lys(Tac) side chain into 3 produced the novel agonist analog 7 (EC(50) = 28 nM in the GPGB) with excellent affinity for both human CCK-A (IC50 = 12 nM) and CCK-B (IC50 = 17 nM) receptors. Analog 7 was a full agonist (EC(50) = 3.5 nM) for calcium mobilization on CHO-K1 cells expressing hCCK-A receptors but a partial agonist on CHO-K1 cells expressing hCCK-B receptors, eliciting a weak agonist reponse (EC(50) = 2800 nM) and antagonizing CCK-8-induced calcium mobilization (K-B = 20 nM). Despite this unusual in vitro profile, analog 7 was a potent anorectic agent in rats (ED(50) = 30 nmol/kg) following intraperitoneal administration.

  DOI：

  10.1021/jm00017a022