3-[4(S)-(Boc-amino)-1,2,4,5-tetrahydro-2-benzazepine-3-one-2-yl]-2(R)-Fmoc-amino-1-(2,6-dimethyl-4-hydroxyphenyl)propane | 854300-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-[4(S)-(Boc-amino)-1,2,4,5-tetrahydro-2-benzazepine-3-one-2-yl]-2(R)-Fmoc-amino-1-(2,6-dimethyl-4-hydroxyphenyl)propane
• 英文别名: tert-butyl N-[(4S)-2-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxy-2,6-dimethylphenyl)propyl]-3-oxo-4,5-dihydro-1H-2-benzazepin-4-yl]carbamate
• CAS: 854300-46-2
• 化学式: C₄₁H₄₅N₃O₆
• 分子量: 675.825
• InChiKey: RWWQQCIOTKSNOX-IIZRLQMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[4(S)-(Boc-amino)-1,2,4,5-tetrahydro-2-benzazepine-3-one-2-yl]-2(R)-Fmoc-amino-1-(2,6-dimethyl-4-hydroxyphenyl)propane 在 三氟乙酸 作用下， 反应 1.0h， 生成 3-(4(S)-amino-1,2,4,5-tetrahydro-2-benzazepine-3-one-2-yl)-2(R)-Fmoc-amino-1(2,6-dimethyl-4-hydroxyphenyl)propane
  参考文献：
  名称：

  A New Structural Motif for μ-Opioid Antagonists

  摘要：

  On the basis of the structural features of the Dmt-Tic pharmacophore, a new motif leading to a fairly potent mu-opioid antagonist is described. This motif contains the 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-one skeleton as a substitute for the Tic residue, which provides the conformational constraint compatible with the mu-opioid receptor. The stereoselective synthesis of four stereoisomers is performed starting from homochiral 2',6'-dimethyltyrosine (Dmt) and o-aminomethylphenylalanine.

  DOI：

  10.1021/jm0491795
• 作为产物：
  描述：

  Fmoc-D-Dmt-N,O-Me2 在 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 3-[4(S)-(Boc-amino)-1,2,4,5-tetrahydro-2-benzazepine-3-one-2-yl]-2(R)-Fmoc-amino-1-(2,6-dimethyl-4-hydroxyphenyl)propane
  参考文献：
  名称：

  A New Structural Motif for μ-Opioid Antagonists

  摘要：

  On the basis of the structural features of the Dmt-Tic pharmacophore, a new motif leading to a fairly potent mu-opioid antagonist is described. This motif contains the 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-one skeleton as a substitute for the Tic residue, which provides the conformational constraint compatible with the mu-opioid receptor. The stereoselective synthesis of four stereoisomers is performed starting from homochiral 2',6'-dimethyltyrosine (Dmt) and o-aminomethylphenylalanine.

  DOI：

  10.1021/jm0491795

文献信息

• A New Structural Motif for μ-Opioid Antagonists
  作者：Isabelle Van den Eynde、Georges Laus、Peter W. Schiller、Piotr Kosson、Nga N. Chung、Andrzej W. Lipkowski、Dirk Tourwé

  DOI：10.1021/jm0491795

  日期：2005.5.1

  On the basis of the structural features of the Dmt-Tic pharmacophore, a new motif leading to a fairly potent mu-opioid antagonist is described. This motif contains the 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-one skeleton as a substitute for the Tic residue, which provides the conformational constraint compatible with the mu-opioid receptor. The stereoselective synthesis of four stereoisomers is performed starting from homochiral 2',6'-dimethyltyrosine (Dmt) and o-aminomethylphenylalanine.