5-methoxy-1,2,3,4-tetrahydronaphthalen-3-ylmethanol | 170353-29-4

• 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-methoxy-1,2,3,4-tetrahydronaphthalen-3-ylmethanol
• 英文别名: 1-(8-methoxy-1,2,3,4-tetrahydronaphth-2-yl)methanol；(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol
• CAS: 170353-29-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: GDPCWZPLQYUXSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 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：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-1,2,3,4-tetrahydronaphthalen-3-ylmethanol 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 4-Benzyl-1-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-piperidine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands

  摘要：

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.

  DOI：

  10.1021/jm049433t
• 作为产物：
  描述：

  8-甲氧基-1,2,3,4-四氢萘-2-甲酸 、 3,8-dimethoxynaphthalene-2-carboxylic acid 在 盐酸 、 sodium hydroxide 、 ammonium chloride 、 氨 、 lithium 作用下， 以 四氢呋喃 、 二甲基硫 、 水 、 叔丁醇 为溶剂， 生成 5-methoxy-1,2,3,4-tetrahydronaphthalen-3-ylmethanol
  参考文献：
  名称：

  Bicyclic aromatic compounds as therapeutic agents

  摘要：

  化合物I的结构如下，并且其药学上可接受的盐，其中A为亚甲基或--O--; B为亚甲基或--O--; g为0、1、2、3或4; R.sub.1、R.sub.2、R.sub.3、R.sub.4、U、Q和T的定义如索赔1所述。这些化合物在治疗中枢神经系统疾病方面具有用途，例如抑郁症、焦虑症、精神病（例如精神分裂症）、迟发性运动障碍、帕金森病、肥胖症、高血压、杜雷特综合征、性功能障碍、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、老年性痴呆、强迫行为、惊恐发作、进食障碍和厌食症、心血管和脑血管疾病、非胰岛素依赖型糖尿病、高血糖、便秘、心律失常、神经内分泌系统疾病、压力、前列腺肥大和痉挛症。

  公开号：

  US05767116A1

文献信息

• [EN] BICYCLIC AROMATIC COMPOUNDS AS THERAPEUTIC AGENTS<br/>[FR] COMPOSES BICYCLIQUES AROMATIQUES UTILISES COMME AGENTS THERAPEUTIQUES
  申请人：KNOLL AG

  公开号：WO1995007274A1

  公开（公告）日：1995-03-16

  (EN) Compounds of formula (I) and pharmaceutically acceptable salts thereof in which A is methylene or -O-; B is methylene or -O-; and g is 0, 1, 2, 3 or 4; U is an alkylene chain optionally substitued by one or more alkyl; Q represents a divalent group containing nitrogen atoms; having utility in the treatment of central nervous system disorders, for example depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, Parkinson's disease, obesity, hypertension, Tourette's syndrome, sexual dysfunction, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, senile dementia, obsessive-compulsive behaviour, panic attacks, eating disorders and anorexia, cardiovascular and cerebrovascular disorders, non-insulin dependent diabetes mellitus, hyperglycaemia, constipation, arrhythmia, disorders of the neuroendocrine system, stress, prostatic hypertrophy, and spasticity.(FR) Composés de la formule (I) et sels pharmaceutiquement acceptables de ces composés; formule dans laquelle A représente méthylène ou -O-; B représente méthylène ou -O-; et g vaut 0, 1, 2, 3, ou 4; U représente une chaîne alkylène éventuellement substituée par au moins un alkyle; et Q représente un groupe bivalent contenant des atomes d'azote. Ces composés conviennent au traitement de troubles du système nerveux central, tels que la dépression, l'anxiété, les psychoses (la schizophrénie, notamment), la dyskinésie tardive, la maladie de Parkinson, l'obésité, l'hypertension, le syndrome de Tourette, le dysfonctionnement sexuel, la toxicomanie, l'abus des drogues, les troubles cognitifs, la maladie d'Alzheimer, la démence sénile, les névroses obsessionnelles, les crises de panique, les troubles alimentaires et l'anorexie, les affections cardiovasculaires et cérébrovasculaires, le diabète sucré non insulino-dépendant, l'hyperglycémie, la constipation, l'arythmie cardiaque, les troubles du système endocrinien, le stress, l'hypertrophie prostatique et la spasmodicité.

  化合物的化学式为(I)，其药物可接受的盐包括：其中A为亚甲基或-O-；B为亚甲基或-O-；g为0、1、2、3或4；U为一种可以被一个或多个烷基取代的烷基链；Q代表含有氮原子的二价基团。这些化合物适用于治疗中枢神经系统疾病，例如抑郁症、焦虑症、精神病（例如精神分裂症）、迟发性运动障碍、帕金森病、肥胖症、高血压、杜雷特综合征、性功能障碍、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、老年性痴呆、强迫症、惊恐发作、进食障碍和厌食症、心血管和脑血管疾病、非胰岛素依赖型糖尿病、高血糖、便秘、心律失常、神经内分泌系统疾病、压力、前列腺肥大和痉挛症。
• BICYCLIC AROMATIC COMPOUNDS AS THERAPEUTIC AGENTS
  申请人：Knoll AG

  公开号：EP0717739A1

  公开（公告）日：1996-06-26
• 1,4-Benzodioxane derivatives having affinity for D2 receptors and utility in the treatment of psychoses
  申请人：Knoll AG

  公开号：EP0717739B1

  公开（公告）日：2000-03-29
• US5767116A
  申请人：——

  公开号：US5767116A

  公开（公告）日：1998-06-16
• Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands
  作者：Luca Costantino、Francesca Gandolfi、Claudia Sorbi、Silvia Franchini、Orazio Prezzavento、Franco Vittorio、Giuseppe Ronsisvalle、Amedeo Leonardi、Elena Poggesi、Livio Brasili

  DOI：10.1021/jm049433t

  日期：2005.1.1

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.