2-(3-chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 133238-88-7

• 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: 2-(3-chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(3-Chloropropyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline；2-(3-chloropropyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
• CAS: 133238-88-7
• 化学式: C₁₄H₂₀ClNO₂
• mdl: MFCD13332033
• 分子量: 269.771
• InChiKey: NVELAMMBCGBXFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基-4-甲氧基联二苯 、 2-(3-chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 sodium hydride 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 1.0h， 以90%的产率得到6,7-dimethoxy-2-(3-((4'-methoxybiphenyl-4-yl)oxy)propyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  SAR Studies on Tetrahydroisoquinoline Derivatives: The Role of Flexibility and Bioisosterism To Raise Potency and Selectivity toward P-glycoprotein

  摘要：

  The development of P-glycoprotein (P-gp) ligands remains of considerable interest, mostly for investigating the protein's structure and transport mechanism. In recent years, many different generations of ligands have been tested for their ability to modulate P-gp activity. The aim of the present work is to perform SAR studies on tetrahydroisoquinoline derivatives in order to design potent and selective P-gp ligands. For this purpose, the effect of bioisosteric replacement and the role of flexibility have been investigated, and four series of tetrahydroisoquinoline ligands have been developed: (a) 2-aryloxazole bioisosteres, (b) elongated analogues, (c) 2H-chromene, and (d) 2-biphenyl derivatives. The results showed that both 2-biphenyl derivative 20b and elongated derivative 6g behaved as strong P-gp substrates. In conclusion, important aspects for developing potent and selective P-gp ligands have been highlighted, providing a solid starting point for further optimization.

  DOI：

  10.1021/jm501640e
• 作为产物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢异喹啉 在 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 2-(3-chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  SAR Studies on Tetrahydroisoquinoline Derivatives: The Role of Flexibility and Bioisosterism To Raise Potency and Selectivity toward P-glycoprotein

  摘要：

  The development of P-glycoprotein (P-gp) ligands remains of considerable interest, mostly for investigating the protein's structure and transport mechanism. In recent years, many different generations of ligands have been tested for their ability to modulate P-gp activity. The aim of the present work is to perform SAR studies on tetrahydroisoquinoline derivatives in order to design potent and selective P-gp ligands. For this purpose, the effect of bioisosteric replacement and the role of flexibility have been investigated, and four series of tetrahydroisoquinoline ligands have been developed: (a) 2-aryloxazole bioisosteres, (b) elongated analogues, (c) 2H-chromene, and (d) 2-biphenyl derivatives. The results showed that both 2-biphenyl derivative 20b and elongated derivative 6g behaved as strong P-gp substrates. In conclusion, important aspects for developing potent and selective P-gp ligands have been highlighted, providing a solid starting point for further optimization.

  DOI：

  10.1021/jm501640e

文献信息

• GUBIN, JEAN;CHATELAIN, PIERRE;INION, HENRI;ROSSEELS, GILBERT
  作者：GUBIN, JEAN、CHATELAIN, PIERRE、INION, HENRI、ROSSEELS, GILBERT

  DOI：——

  日期：——
• GUBIN, JEAN;CHATELAIN, PIERRE;LUCHETTI, JEAN
  作者：GUBIN, JEAN、CHATELAIN, PIERRE、LUCHETTI, JEAN

  DOI：——

  日期：——
• TRIAZOLVERBINDUNGEN MIT DOPAMIN-D3-REZEPTORAFFINITÄT
  申请人：Abbott GmbH & Co. KG

  公开号：EP1144405B1

  公开（公告）日：2009-11-25
• US5340820A
  申请人：——

  公开号：US5340820A

  公开（公告）日：1994-08-23
• US5565470A
  申请人：——

  公开号：US5565470A

  公开（公告）日：1996-10-15