N,N(Me)2-Dmt-Aia-Gly-OH | 1122622-09-6

• 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,N(Me)2-Dmt-Aia-Gly-OH
• 英文别名: 2-((S)-4-((S)-2-(dimethylamino)-3-(4-hydroxy-2,6-dimethylphenyl)propanamido)-3-oxo-4,5-dihydroazepino[3,4-b]indol-2(1H,3H,10H)-yl)acetic acid；2-[(4S)-4-[[(2S)-2-(dimethylamino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]amino]-3-oxo-1,4,5,10-tetrahydroazepino[3,4-b]indol-2-yl]acetic acid
• CAS: 1122622-09-6
• 化学式: C₂₇H₃₂N₄O₅
• 分子量: 492.575
• InChiKey: XTEHMRJXZGIECL-UPVQGACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N(Me)2-Dmt-Aia-Gly-OH 、 乙二胺 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2S)-2-(dimethylamino)-N-[(4S)-2-[2-[2-[[2-[(4S)-4-[[(2S)-2-(dimethylamino)-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]amino]-3-oxo-1,4,5,10-tetrahydroazepino[3,4-b]indol-2-yl]acetyl]amino]ethylamino]-2-oxoethyl]-3-oxo-1,4,5,10-tetrahydroazepino[3,4-b]indol-4-yl]-3-(4-hydroxy-2,6-dimethylphenyl)propanamide
  参考文献：
  名称：

  Novel multiple opioid ligands based on 4-aminobenzazepinone (Aba), azepinoindole (Aia) and tetrahydroisoquinoline (Tic) scaffolds

  摘要：

  The dimerization and trimerization of the Dmt-Tic, Dmt-Aia and Dmt-Aba pharmacophores provided multiple ligands which were evaluated in vitro for opioid receptor binding and functional activity. Whereas the Tic-and Aba multimers proved to be dual and balanced delta/mu antagonists, as determined by the functional [S(35)] GTP gamma S binding assay, the dimerization of potent Aia-based 'parent' ligands unexpectedly resulted in substantial less efficient receptor binding and non-active dimeric compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.055