N-[(2-tert-butyloxycarbonyl)-2-adamantyl] (2S)-2-N-(9-fluorenylmethyloxycarbonyl)amino-3-(4-tert-butyloxyphenyl)propanamide | 502937-08-8

• 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-[(2-tert-butyloxycarbonyl)-2-adamantyl] (2S)-2-N-(9-fluorenylmethyloxycarbonyl)amino-3-(4-tert-butyloxyphenyl)propanamide
• CAS: 502937-08-8
• 化学式: C₄₃H₅₂N₂O₆
• 分子量: 692.896
• InChiKey: LFEBWSQNJCBZCW-MLTTVHPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[(2-tert-butyloxycarbonyl)-2-adamantyl] (2S)-2-N-(9-fluorenylmethyloxycarbonyl)amino-3-(4-tert-butyloxyphenyl)propanamide 在 哌啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 N-{(2S)-1-[(2-hydroxycarbonyl)-2-adamantylamino]-3-(4-hydroxyphenyl)-1-oxo-propan-2-yl} 1-(6-guanidinohexyl)-6-(5-guanidinopentyloxy)indole-2-carboxamide bis(trifluoroacetate)
  参考文献：
  名称：

  Synthesis and Biological Studies of Novel Neurotensin(8–13) Mimetics

  摘要：

  Novel neurotensin (NT) (8-13) (Arg(8)-Arg(9)-Pro(10)-Tyr(11)-Ile(12)-Leu(13)) mimetics 3, 4 were designed by adopting all intrinsic functional groups of the native neurotensin(8-13) and using a substituted indole as a template to mimic the pharmacophore of NT(8-13). Biological studies at subtype 1 of the NT receptor showed that 3 has a 55 and 580 nM binding affinity at rat and human neurotensin receptors, respectively, As a comparison. compounds 5 and 6 were also synthesized. The binding difference between 3, 4 and 5, 6 argues the importance of the carboxylic group in achieving higher potency NT(8-13) mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00342-5
• 作为产物：
  描述：

  2-N-benzyloxycarbonylamino-2-tert-butyloxycarbonyl-adamantane 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[(2-tert-butyloxycarbonyl)-2-adamantyl] (2S)-2-N-(9-fluorenylmethyloxycarbonyl)amino-3-(4-tert-butyloxyphenyl)propanamide
  参考文献：
  名称：

  Synthesis and Biological Studies of Novel Neurotensin(8–13) Mimetics

  摘要：

  Novel neurotensin (NT) (8-13) (Arg(8)-Arg(9)-Pro(10)-Tyr(11)-Ile(12)-Leu(13)) mimetics 3, 4 were designed by adopting all intrinsic functional groups of the native neurotensin(8-13) and using a substituted indole as a template to mimic the pharmacophore of NT(8-13). Biological studies at subtype 1 of the NT receptor showed that 3 has a 55 and 580 nM binding affinity at rat and human neurotensin receptors, respectively, As a comparison. compounds 5 and 6 were also synthesized. The binding difference between 3, 4 and 5, 6 argues the importance of the carboxylic group in achieving higher potency NT(8-13) mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00342-5