(S)-1-(6-((diethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)-4-(4-fluorophenethyl)piperazin-2-one | 928675-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-1-(6-((diethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)-4-(4-fluorophenethyl)piperazin-2-one
• 英文别名: 1-[(2S)-6-(diethylaminomethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[2-(4-fluorophenyl)ethyl]piperazin-2-one
• CAS: 928675-03-0
• 化学式: C₂₇H₃₆FN₃O
• 分子量: 437.601
• InChiKey: XWZAXTGZXFCRFU-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(6-((diethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)-4-(4-fluorophenethyl)piperazin-2-one 在 氯甲酸乙酯 作用下， 以 乙腈 为溶剂， 反应 0.16h， 生成 (S)-4-(4-fluorophenethyl)-1-(6-((2,2,2-trifluoroethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)piperazin-2-one
  参考文献：
  名称：

  Aminomethyl tetrahydronaphthalene ketopiperazine MCH-R1 antagonists—Increasing selectivity over hERG

  摘要：

  A direct correlation between hERG binding and QTc prolongation was established for a series of aminomethyl tetrahydronaphthalene ketopiperazine MCH-R1 antagonists. Compounds within this class with greater selectivity over hERG were developed. Compound 4h proved to have the best profile, with MCH-R1 K-i = 16 nm and hERG IC50 = 25 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.052
• 作为产物：
  描述：

  4-氟苯乙胺 在 镍 氨 、 氢气 、 三乙酰氧基硼氢化钠 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.75h， 生成 (S)-1-(6-((diethylamino)methyl)-1,2,3,4-tetrahydronaphthalen-2-yl)-4-(4-fluorophenethyl)piperazin-2-one
  参考文献：
  名称：

  The efficacy and cardiac evaluation of aminomethyl tetrahydronaphthalene ketopiperazines: A novel class of potent MCH-R1 antagonists

  摘要：

  The design, synthesis, and biological studies of a novel class of MCH-R1 antagonists based on an amino tetrahydronaphthalene ketopiperazine scaffold is described. Compounds within this class promoted significant body weight reduction in mouse diet induced obesity studies. The potential for hERG blockage activity and QT interval studies in anesthetized dogs are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.028

文献信息

• The efficacy and cardiac evaluation of aminomethyl tetrahydronaphthalene ketopiperazines: A novel class of potent MCH-R1 antagonists
  作者：José L. Méndez-Andino、Anny-Odile Colson、Kenneth M. Meyers、Maria C. Mitchell、Karen Hodge、Jeremy M. Howard、Nicholas Kim、David C. Ackley、Jerry K. Holbert、Scott W. Mittelstadt、Martin E. Dowty、Cindy M. Obringer、Paula Suchanek、Ofer Reizes、X. Eric Hu、John A. Wos

  DOI：10.1016/j.bmc.2006.12.028

  日期：2007.3

  The design, synthesis, and biological studies of a novel class of MCH-R1 antagonists based on an amino tetrahydronaphthalene ketopiperazine scaffold is described. Compounds within this class promoted significant body weight reduction in mouse diet induced obesity studies. The potential for hERG blockage activity and QT interval studies in anesthetized dogs are discussed. (c) 2007 Elsevier Ltd. All rights reserved.
• Aminomethyl tetrahydronaphthalene ketopiperazine MCH-R1 antagonists—Increasing selectivity over hERG
  作者：Kenneth M. Meyers、José L. Méndez-Andino、Anny-Odile Colson、Namal C. Warshakoon、John A. Wos、Maria C. Mitchell、Karen M. Hodge、Jeremy M. Howard、David C. Ackley、Jerry K. Holbert、Scott W. Mittelstadt、Martin E. Dowty、Cindy M. Obringer、Ofer Reizes、X. Eric Hu

  DOI：10.1016/j.bmcl.2006.10.052

  日期：2007.2

  A direct correlation between hERG binding and QTc prolongation was established for a series of aminomethyl tetrahydronaphthalene ketopiperazine MCH-R1 antagonists. Compounds within this class with greater selectivity over hERG were developed. Compound 4h proved to have the best profile, with MCH-R1 K-i = 16 nm and hERG IC50 = 25 mu M. (c) 2006 Elsevier Ltd. All rights reserved.