(RS)-2-dimethylamino-methyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one | 62620-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (RS)-2-dimethylamino-methyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 2-dimethylaminomethyl-6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene；2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one；6-methoxy-2-dimethylaminomethyl-3,4-dihydro-2H-naphthalen-1-one；2-[(dimethylamino)methyl]-3,4-dihydro-6-methoxy-1(2H)-naphthalenone；2-dimethylaminomethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one；(+/-)-6-Methoxy-1-oxo-2-(dimethylamino-methyl)-1.2.3.4-tetrahydro-naphthalin；2-[(dimethylamino)methyl]-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 62620-37-5
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SEAVJROPZNGJBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-2-dimethylamino-methyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以97%的产率得到trans-6-methoxy-2-dimethylaminomethyl-1,2,3,4-tetrahydronaphthalen-1-ol
  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：

  6-甲氧基-1-萘满酮 以45%的产率得到
  参考文献：
  名称：

  Collins David J., Fallon Gary D., Skene Colin E., Austral. J. Chem, 47 (1994) N 4, S 623-648

  摘要：

  DOI：

文献信息

• Nitrogen-containing heterocyclic compounds as class III antiarrhythmic
  申请人：Merck & Co., Inc.

  公开号：US05215989A1

  公开（公告）日：1993-06-01

  Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members, X and Y are bridging groups, Q is a nitrogen containing heterocycle, R.sup.2 and R.sup.3 are H, substituted or unsubtituted C.sub.1-3 alkyl, C.sub.1-3 alkoxy, N(R).sub.2, halogen, CF.sub.3 or R.sup.5 and R.sup.1 is H or an aryl group.

  结构式化合物：##STR1## 其中Ar是芳香环，B是与Ar融合的5-7个成员的环状基团，X和Y是桥接基团，Q是含氮杂环，R.sup.2和R.sup.3是H，取代或未取代的C.sub.1-3烷基，C.sub.1-3烷氧基，N(R).sub.2，卤素，CF.sub.3或R.sup.5，R.sup.1是H或芳基。
• Nitrogens containing heterocyclic compounds as class III antiarrhythmic
  申请人：Merck & Co., Inc.

  公开号：US05032598A1

  公开（公告）日：1991-07-16

  Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members and Q is a nitrogen containing heterocycle, are antiarrhythmic agents.

  结构式化合物：##STR1## 其中 Ar 是芳香环，B 是与 Ar 融合的含有 5-7 个成员的环状基团，Q 是含氮杂环，是抗心律失常药物。
• 1,3,8-Triazaspiro(4.5)decan-4-one derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04051248A1

  公开（公告）日：1977-09-27

  Compounds having the structure ##STR1## and the pharmaceutically acceptable salts thereof, wherein R.sub.1 is hydrogen, halogen, hydroxy, alkanoyloxy, alkoxy, alkylthio, alkyl or trifluoromethyl; R.sub.2 is hydrogen, alkyl or alkenyl; R.sub.3 is hydrogen, halogen or alkyl; R.sub.4 is formyloxy or alkanoyloxy; m is 1 or 2; and n is 0, 1 or 2; have useful physiological activity.

  具有结构##STR1##及其药用可接受盐的化合物，其中R.sub.1为氢、卤素、羟基、烷酰氧基、烷氧基、烷基硫基、烷基或三氟甲基；R.sub.2为氢、烷基或烯基；R.sub.3为氢、卤素或烷基；R.sub.4为甲酰氧基或烷酰氧基；m为1或2；n为0、1或2；具有有用的生理活性。
• Substituted amino compounds and their use as substances having an
  申请人：Gruenenthal GmbH

  公开号：US06022895A1

  公开（公告）日：2000-02-08

  Substituted amino compounds of general formula (I) ##STR1## are described, as are a method of preparing them and their use as drugs, especially as analgesics.

  通式（I）##STR1## 的氨基取代化合物被描述，以及制备它们的方法和它们作为药物的用途，特别是作为镇痛剂。
• Further exploration of 1-{2-[Bis-(4-fluorophenyl)methoxy]ethyl}piperazine (GBR 12909): role of N-aromatic, N-heteroaromatic, and 3-oxygenated N-phenylpropyl substituents on affinity for the dopamine and serotonin transporter
  作者：David Lewis、Ying Zhang、Thomas Prisinzano、Christina M. Dersch、Richard B. Rothman、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1016/s0960-894x(03)00108-2

  日期：2003.4

  N-phenylpropyl derivatives of 1-(2-benzhydryloxyethyl)-piperazine and 1-[2-[bis-(4-fluorophenyl)methoxy]ethyl]piperazine, analogues of GBR 12909 (1a) and 12935 (1b), was synthesized and examined for their dopamine (DAT) and serotonin (SERT) transporter binding properties. One of these compounds, racemic 3-[4-(2-benzhydryloxyethyl)piperazin-1-yl]-1-(3-fluorophenyl)-propan-1-ol (33), had DAT affinity as good as

  1-（2-苯甲酰氧基乙基）-哌嗪和1- [2- [双-（双-（4-氟苯基）甲氧基]乙基]哌嗪的一系列N-芳族，N-杂芳族和氧化的N-苯基丙基衍生物，GBR的类似物合成了12909（1a）和12935（1b）并检查了它们的多巴胺（DAT）和血清素（SERT）转运蛋白结合特性。这些化合物中的一种，即外消旋的3- [4-（2-苯甲氧基氧基乙基）哌嗪-1-基] -1-（3-氟苯基）-丙-1-醇（33），其DAT亲和力与或优于，GBR 12909和12935，并且比GBR化合物对SAT的DAT更具选择性。反式（43）和顺式（47）（+/-）-2-（4- [2- [双-（4-氟苯基）-甲氧基]乙基]哌嗪-1-基甲基）-6-甲氧基- 1,2,3,4-四氢萘-1-醇具有相对较好的SERT选择性，并且对SERT也具有很高的亲和力。