(S)-2-[(2S,3S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester | 202860-55-7

• 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: (S)-2-[(2S,3S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester
• CAS: 202860-55-7
• 化学式: C₃₄H₄₀N₂O₆
• 分子量: 572.701
• InChiKey: GRLHRVKEPJNPBL-TVHSXNCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2S,3S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 (S)-2-[(2S,3S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid; hydrochloride
  参考文献：
  名称：

  The stereochemical requirements of the novel δ-opioid selective dipeptide antagonist TMT-Tic

  摘要：

  Five conformationally constrained dipeptide TMT-L-Tic analogues have been synthesized and evaluated for their bioactivity using in vitro bioassays. The most potent and selective analogue (2S,SR)-TMT-L-Tic showed 9 nM binding affinity and 4000-fold selectivity for the delta vs mu opioid receptor. The lowest-energy conformation of(2S,3R)-TMT-L-Tic is suggested to be bioactive one in which the chi(1) torsional angle is trans for TMT and gauche (+) for Tic. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10145-7
• 作为产物：
  描述：

  3-benzyl 2-tert-butyl (S)-1,2,3,4-tetrahydroisoquinoline-2,3(1H)dicarboxylate 在 盐酸 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-[(2S,3S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  The stereochemical requirements of the novel δ-opioid selective dipeptide antagonist TMT-Tic

  摘要：

  Five conformationally constrained dipeptide TMT-L-Tic analogues have been synthesized and evaluated for their bioactivity using in vitro bioassays. The most potent and selective analogue (2S,SR)-TMT-L-Tic showed 9 nM binding affinity and 4000-fold selectivity for the delta vs mu opioid receptor. The lowest-energy conformation of(2S,3R)-TMT-L-Tic is suggested to be bioactive one in which the chi(1) torsional angle is trans for TMT and gauche (+) for Tic. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10145-7