Fmoc-D-Dmt(Moc)-N,O-Me2 | 854300-36-0

• 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: Fmoc-D-Dmt(Moc)-N,O-Me2
• 英文别名: [4-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[methoxy(methyl)amino]-3-oxopropyl]-3,5-dimethylphenyl] methyl carbonate
• CAS: 854300-36-0
• 化学式: C₃₀H₃₂N₂O₇
• 分子量: 532.593
• InChiKey: KALCRDFJYOEHPY-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-D-Dmt(Moc)-N,O-Me2 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 [1-(4-hydroxy-2,6-dimethylbenzyl)-2(R)-(3-oxo-4(S)-phenylacetylamino-1,2,4,5-tetrahydrobenzo[c]azepin-2-yl)-ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester
  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-OH 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 4.0h， 生成 Fmoc-D-Dmt(Moc)-N,O-Me2
  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.