(3S)-6-bromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid | 262616-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (3S)-6-bromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• CAS: 262616-23-9
• 化学式: C₁₀H₁₀BrNO₃
• 分子量: 272.098
• InChiKey: BRUWBMFTCKACDE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S)-6-bromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 在 盐酸 、 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Novel Dmt-Tic dipeptide analogues as selective delta-opioid receptor antagonists

  摘要：

  A series of Dmt-Tic analogues with substitution on the Tic aromatic ring has been synthesized and evaluated for opioid receptor affinity and activation. Incorporation of large hydrophobic groups at position 7 of Tic did not greatly alter the delta opioid receptor binding affinities of the dipeptides whereas substitution at position 6 substantially diminished their affinity. These modified Dmt-Tic peptides showed binding affinities as low as 2.5 nM with up to 500-fold selectivity for the delta versus mu opioid receptor and proved to be 6 receptor antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00652-6
• 作为产物：
  描述：

  L-7-羟基-1,2,3,4-四氢异喹啉-3-羧酸 在 溴 、 溶剂黄146 作用下， 生成 (S)-6,8-Dibromo-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid 、 (3S)-6-bromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel Dmt-Tic dipeptide analogues as selective delta-opioid receptor antagonists

  摘要：

  A series of Dmt-Tic analogues with substitution on the Tic aromatic ring has been synthesized and evaluated for opioid receptor affinity and activation. Incorporation of large hydrophobic groups at position 7 of Tic did not greatly alter the delta opioid receptor binding affinities of the dipeptides whereas substitution at position 6 substantially diminished their affinity. These modified Dmt-Tic peptides showed binding affinities as low as 2.5 nM with up to 500-fold selectivity for the delta versus mu opioid receptor and proved to be 6 receptor antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00652-6