trans-2-(Dimethylaminomethyl)-1,2,3,4-tetrahydro-naphthalinol | 122431-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-2-(Dimethylaminomethyl)-1,2,3,4-tetrahydro-naphthalinol
• 英文别名: trans-2-dimethylaminomethyl-1,2,3,4-tetrahydronaphthalen-1-ol；(1R,2R)-2-[(dimethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 122431-60-1
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: DPGLJDFBUJEPKW-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-(Dimethylaminomethyl)-1,2,3,4-tetrahydro-naphthalinol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 14.25h， 生成 cis-dimethyl-[1-phenoxy-1,2,3,4-tetrahydronaphthalen-2-ylmethyl]-amine
  参考文献：
  名称：

  Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine

  摘要：

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.032
• 作为产物：
  描述：

  2-[(二甲基氨基)甲基]四氢萘-1-酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以97%的产率得到trans-2-(Dimethylaminomethyl)-1,2,3,4-tetrahydro-naphthalinol
  参考文献：
  名称：

  Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine

  摘要：

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.032

文献信息

• Novel antidepressants
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0303961A2

  公开（公告）日：1989-02-22

  The present invention provides novel compounds such as certain aryloxy indanamines which are useful as anti-­depressants and as inhibitors of synaptic norepinephrine and serotonin uptake. The present invention also provides an improvement in the treatment of depression which comprises inhibiting synaptic serotonin and epinepherine uptake.

  本发明提供了新型化合物，如某些芳氧基茚满胺，它们可用作抗抑郁剂和突触去甲肾上腺素和血清素摄取抑制剂。本发明还提供了一种治疗抑郁症的改进方法，其中包括抑制突触5-羟色胺和表啡肽的摄取。
• Synthesis and structure–activity relationships of selective norepinephrine reuptake inhibitors (sNRI) with a heterocyclic ring constraint
  作者：Sarah Hudson、Mehrak Kiankarimi、Wendy Eccles、Yalda S. Mostofi、Marc J. Genicot、Wesley Dwight、Beth A. Fleck、Kathleen Gogas、Warren S. Wade

  DOI：10.1016/j.bmcl.2008.07.050

  日期：2008.8

  The design, synthesis and SAR of a series of heterocyclic ring-constrained norepinephrine reuptake inhibitors are described. As racemates, the best compounds compare favorably with atomoxetine (IC50's < 10 nM) in potency at the transporter. (c) 2008 Elsevier Ltd. All rights reserved.
• Risch, Nikolaus; Esser, Achim, Liebigs Annalen der Chemie, 1992, # 3, p. 233 - 238
  作者：Risch, Nikolaus、Esser, Achim

  DOI：——

  日期：——
• Phenoxy and phenylthio, amino substituted benzocycloalkane derivatives in the treatment and prevention of drug-resistant protozoal infections
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0371508B1

  公开（公告）日：1993-07-14
• US5134168A
  申请人：——

  公开号：US5134168A

  公开（公告）日：1992-07-28