(S)-6-Bromo-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester | 262616-25-1

• 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)-6-Bromo-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester
• CAS: 262616-25-1
• 化学式: C₁₆H₂₀BrNO₅
• 分子量: 386.243
• InChiKey: KVGHKPOHOGAJDI-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-6-Bromo-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 在 盐酸 、 lithium hydroxide 、 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.5h， 生成 (S)-2-[2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-7-methoxy-6-(4-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline-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
• 作为产物：
  描述：

  (3S)-6-bromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 苯 为溶剂， 反应 16.5h， 生成 (S)-6-Bromo-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester
  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