2,2'-ethylenebis<7,8-dichloro-1,2,3,4-tetrahydroisoquinoline> | 76993-31-2

• 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: 2,2'-ethylenebis<7,8-dichloro-1,2,3,4-tetrahydroisoquinoline>
• 英文别名: 2,2'-ethylenebis(7,8-dichloro-1,2,3,4-tetrahydroisoquinoline)；7,8-Dichloro-2-[2-(7,8-dichloro-1,2,3,4-tetrahydro-2-isoquinolinyl)ethyl]-1,2,3,4-tetrahydroisoquinoline; dihydrochloride；7,8-dichloro-2-[2-(7,8-dichloro-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]-3,4-dihydro-1H-isoquinoline
• CAS: 76993-31-2
• 化学式: C₂₀H₂₀Cl₄N₂
• 分子量: 430.204
• InChiKey: VFZLGMHUYYLKHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7,8-二氯-1,2,3,4-四氢异喹啉 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 2,2'-ethylenebis<7,8-dichloro-1,2,3,4-tetrahydroisoquinoline>
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 3. Bis[tetrahydroisoquinoline]s

  摘要：

  7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (SK&F 64139) is a potent inhibitor of phenylethanolamine N-methyltransferase (IC50 = 10 muM) that may have therapeutic utility in man. A series of related compounds in which two 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline molecules have been bridged from nitrogen to nitrogen by an unbranched alkyl chain have been prepared and have demonstrated potent inhibitory properties (0.08 to 2 muM). In contrast simple substitution on the nitrogen of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline with a variety of substituents gives compounds with greatly diminished inhibitory potencies (IC50 = 2 to greater than 100 muM) relative to SK&F 64139. Kinetic studies with a C6 analogue have shown that it is competitive with respect to phenylethanolamine and uncompetitive with respect to S-adenosylmethionine. The increased potency of some of the bis analogues relative to that seen with the tetrahydroisoquinolines having larger alkyl groups on nitrogen suggests that several of the bis compounds show supplemented or cooperative binding to the enzyme, presumably as a result of the second tetrahydroisoquinoline moiety.

  DOI：

  10.1021/jm00138a023

文献信息

• Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 3. Bis[tetrahydroisoquinoline]s
  作者：R. M. DeMarinis、W. M. Bryan、L. M. Hillegass、D. McDermott、R. G. Pendleton

  DOI：10.1021/jm00138a023

  日期：1981.6

  7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (SK&F 64139) is a potent inhibitor of phenylethanolamine N-methyltransferase (IC50 = 10 muM) that may have therapeutic utility in man. A series of related compounds in which two 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline molecules have been bridged from nitrogen to nitrogen by an unbranched alkyl chain have been prepared and have demonstrated potent inhibitory properties (0.08 to 2 muM). In contrast simple substitution on the nitrogen of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline with a variety of substituents gives compounds with greatly diminished inhibitory potencies (IC50 = 2 to greater than 100 muM) relative to SK&F 64139. Kinetic studies with a C6 analogue have shown that it is competitive with respect to phenylethanolamine and uncompetitive with respect to S-adenosylmethionine. The increased potency of some of the bis analogues relative to that seen with the tetrahydroisoquinolines having larger alkyl groups on nitrogen suggests that several of the bis compounds show supplemented or cooperative binding to the enzyme, presumably as a result of the second tetrahydroisoquinoline moiety.