1-[(3,5-Dimethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline | 1398121-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-[(3,5-Dimethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline
• CAS: 1398121-00-0
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: KVUHVVDCQGXSOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(3,5-Dimethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline 在 甲酸 、 (S,S)-N-(对甲苯磺酰)-1,2-二苯乙烷二胺(对异丙基苯)氯化钌(II) 、 三乙胺 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (S)-1-((3,5-dimethylphenyl)methyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: Selective inhibitors of dopamine D1 receptor

  摘要：

  A series of new tetrahydroprotoberberine (THPB) derivatives were designed, synthesized, and tested for their binding affinity towards dopamine (D-1 and D-2) and serotonin (5-HT1A and 5-HT2A) receptors. Many of the THPB compounds exhibited high binding affinity and activity at the dopamine D-1 receptor, as well as high selectivity for the D-1 receptor over the D-2, 5-HT1A, and 5-HT2A receptors. Among these, compound 19c exhibited a promising D-1 receptor binding affinity (K-i = 2.53 nM) and remarkable selectivity versus D2R (inhibition = 81.87%), 5-HT1AR (inhibition = 61.70%), and 5-HT2AR (inhibition = 24.96%). Compared with l-(S)-stepholidine (l-SPD) (D-1 K-i = 6.23 nM, D-2 K-i = 56.17 nM), compound 19c showed better binding affinity for the D-1 receptor (2.5-fold higher) and excellent D-2/D-1 selectivity. Functional assays found compounds 18j, 18k, and 19c are pure D-1 receptor antagonists. These results indicate that removing the C10 hydroxy group and introducing a methoxy group at C11 of the pharmacophore of l-SPD can reverse the function of THPB compounds at the D-1 receptor. These results are in accord with molecular docking studies. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.057
• 作为产物：
  描述：

  1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 在 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 11.5h， 生成 1-[(3,5-Dimethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: Selective inhibitors of dopamine D1 receptor

  摘要：

  A series of new tetrahydroprotoberberine (THPB) derivatives were designed, synthesized, and tested for their binding affinity towards dopamine (D-1 and D-2) and serotonin (5-HT1A and 5-HT2A) receptors. Many of the THPB compounds exhibited high binding affinity and activity at the dopamine D-1 receptor, as well as high selectivity for the D-1 receptor over the D-2, 5-HT1A, and 5-HT2A receptors. Among these, compound 19c exhibited a promising D-1 receptor binding affinity (K-i = 2.53 nM) and remarkable selectivity versus D2R (inhibition = 81.87%), 5-HT1AR (inhibition = 61.70%), and 5-HT2AR (inhibition = 24.96%). Compared with l-(S)-stepholidine (l-SPD) (D-1 K-i = 6.23 nM, D-2 K-i = 56.17 nM), compound 19c showed better binding affinity for the D-1 receptor (2.5-fold higher) and excellent D-2/D-1 selectivity. Functional assays found compounds 18j, 18k, and 19c are pure D-1 receptor antagonists. These results indicate that removing the C10 hydroxy group and introducing a methoxy group at C11 of the pharmacophore of l-SPD can reverse the function of THPB compounds at the D-1 receptor. These results are in accord with molecular docking studies. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.057

文献信息

• DERIVATIVES OF PAPAVERINE THAT ARE EFFECTIVE HYPOXIC TUMOR RADIOSENSITIZERS
  申请人：Ohio State Innovation Foundation

  公开号：US20210163453A1

  公开（公告）日：2021-06-03

  Disclosed herein are compounds, compositions, and methods for inhibiting mitochondrial oxygen consumption in a cancerous tissue. The compounds, compositions, and methods can be used to treat a subject with hypoxic cancerous tissue.
• [EN] DERIVATIVES OF PAPAVERINE THAT ARE EFFECTIVE HYPOXIC TUMOR RADIOSENSITIZERS<br/>[FR] DÉRIVÉS DE PAPAVÉRINE QUI SONT DES RADIOSENSIBILISATEURS DE TUMEURS HYPOXIQUES EFFICACES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2020023537A1

  公开（公告）日：2020-01-30

  Disclosed herein are compounds, compositions, and methods for inhibiting mitochondrial oxygen consumption in a cancerous tissue. The compounds, compositions, and methods can be used to treat a subject with hypoxic cancerous tissue.