[1-(4-hydroxy-2,6-dimethylbenzyl)-2(S)-(3-oxo-4(S)-phenylacetylamino-1,2,4,5-tetrahydrobenzo[c]azepin-2-yl)-ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester | 854300-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [1-(4-hydroxy-2,6-dimethylbenzyl)-2(S)-(3-oxo-4(S)-phenylacetylamino-1,2,4,5-tetrahydrobenzo[c]azepin-2-yl)-ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-1-(4-hydroxy-2,6-dimethylphenyl)-3-[(4S)-3-oxo-4-[(2-phenylacetyl)amino]-4,5-dihydro-1H-2-benzazepin-2-yl]propan-2-yl]carbamate
• CAS: 854300-52-0
• 化学式: C₄₄H₄₃N₃O₅
• 分子量: 693.843
• InChiKey: SICFBTCZBBKZBJ-GCBNJDDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  52
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-(4-hydroxy-2,6-dimethylbenzyl)-2(S)-(3-oxo-4(S)-phenylacetylamino-1,2,4,5-tetrahydrobenzo[c]azepin-2-yl)-ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,4-二巯基-2,3-丁二醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propyl]-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl}-2-phenyl-acetamide
  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-L-Dmt-N,O-Me2 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.5h， 生成 [1-(4-hydroxy-2,6-dimethylbenzyl)-2(S)-(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