N-[2-(Benzoxazol-5-yl)ethyl]-N-[(R)-(+)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]-N-methylamine | 152148-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-[2-(Benzoxazol-5-yl)ethyl]-N-[(R)-(+)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]-N-methylamine
• 英文别名: (2-Benzooxazol-5-yl-ethyl)-((R)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-methyl-amine；2-(1,3-benzoxazol-5-yl)-N-[[(1R)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-N-methylethanamine
• CAS: 152148-80-6
• 化学式: C₂₂H₂₆N₂O₂
• 分子量: 350.461
• InChiKey: HXRQZCLRSJMHTR-KRWDZBQOSA-N

物化性质

• 沸点：
  499.3±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 在 palladium catalyst 硼烷四氢呋喃络合物 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.0h， 生成 N-[2-(Benzoxazol-5-yl)ethyl]-N-[(R)-(+)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ylmethyl]-N-methylamine
  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

• 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
• [EN] TERTIARY AND SECONDARY AMINES AS ALPHA-2 ANTAGONISTS AND SEROTONIN UPTAKE INHIBITORS
  申请人：——

  公开号：WO1993012754A2

  公开（公告）日：1993-07-08

  [EN] The present invention provides an amine compound of formula (I) or a pharmaceutically acceptable salt thereof which is an antagonist for alpha-2 adrenoreceptors and which inhibits serotonin (5-hydroxytryptamine, 5-HT) uptake.
  [FR] La présente invention se rapporte à un composé d'amines de la formule (I) ou un sel pharmaceutique acceptable de celui-ci qui est un antagoniste destiné aux adrénorécepteurs alpha-2 et qui inhibe la fixation de la sérotonine (5-hydroxytryptamine, 5-HT).