1-<6-azido-5-(R)-<<(tert-butyloxy)carbonyl>amino>hexyl>-3-o-tolylura | 166446-75-9

• 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: 1-<6-azido-5-(R)-<<(tert-butyloxy)carbonyl>amino>hexyl>-3-o-tolylura
• 英文别名: tert-butyl N-[(2R)-1-azido-6-[(2-methylphenyl)carbamoylamino]hexan-2-yl]carbamate
• CAS: 166446-75-9
• 化学式: C₁₉H₃₀N₆O₃
• 分子量: 390.486
• InChiKey: LEAZNEMJFBBLHV-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<6-azido-5-(R)-<<(tert-butyloxy)carbonyl>amino>hexyl>-3-o-tolylura 在 palladium on activated charcoal 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 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 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 在 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.75h， 生成 1-<6-azido-5-(R)-<<(tert-butyloxy)carbonyl>amino>hexyl>-3-o-tolylura
  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