5-{2-[((R)-(+)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)methyl-amino]-ethyl}-1,3-dihydro-indol-2-one | 152149-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-{2-[((R)-(+)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)methyl-amino]-ethyl}-1,3-dihydro-indol-2-one
• 英文别名: 5-{2-[((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amino]-ethyl}-1,3-dihydro-indol-2-one；5-[2-[[(1R)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]methyl-methylamino]ethyl]-1,3-dihydroindol-2-one
• CAS: 152149-36-5
• 化学式: C₂₃H₂₈N₂O₂
• 分子量: 364.488
• InChiKey: BYHTZWPPZDLFLX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲氧基-3,4-二氢-2H-1-萘酮 在 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基十二/十四烷基叔胺 、 锂丁酯 、 lithium carbonate 、 对甲苯磺酸 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙二醇 、 乙腈 、 苯 为溶剂， 反应 127.75h， 生成 5-{2-[((R)-(+)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)methyl-amino]-ethyl}-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m

文献信息

• Treatment of movement disorders by administration of 5-hydroxytryptamine receptor/alpha2 adrenergic receptor antagonist compositions
  申请人：——

  公开号：US20020035057A1

  公开（公告）日：2002-03-21

  A method of combating movement disorder in a patient experiencing or susceptible to same, by administering to the patient an effective amount of a neurotransmission modulating composition including a 5HT antagonist and/or &agr; 2 antagonist. The antagonist may for example include a piperazinoazepine compound such as mirtazapine that is a receptor antagonist for 5HT2/3 and &agr; 2 receptors.

  一种防治运动障碍患者或易患运动障碍患者运动障碍的方法，通过向患者施用有效量的神经传递调节组合物，包括 5HT 拮抗剂和/或 &agr； 2 拮抗剂。例如，拮抗剂可包括哌嗪氮杂卓化合物，如米氮平，它是 5HT2/3 和 &agr； 2 受体的拮抗剂。
• TERTIARY AND SECONDARY AMINES AS ALPHA-2 ANTAGONISTS AND SEROTONIN UPTAKE INHIBITORS
  申请人：ABBOTT LABORATORIES

  公开号：EP0646112A1

  公开（公告）日：1995-04-05
• EP0646112A4
  申请人：——

  公开号：EP0646112A4

  公开（公告）日：1997-04-02
• US5288749A
  申请人：——

  公开号：US5288749A

  公开（公告）日：1994-02-22
• US6281207B1
  申请人：——

  公开号：US6281207B1

  公开（公告）日：2001-08-28