2-(4-pyridinyl)tetralone | 137537-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(4-pyridinyl)tetralone
• 英文别名: 2-(4-pyridyl)tetralone；2-(4-Pyridyl)-1-tetralon；2-pyridin-4-yl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 137537-22-5
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: OTFJCDWGHSIXMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-pyridinyl)tetralone 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 2-(1-Benzyl-piperidin-4-yl)-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Piperidinyltetralin .sigma. Ligands

  摘要：

  sigma receptor ligands have been proposed to be potential antipsychotic drugs based on their activity profile in animal behavioral models and their indirect modulation of dopaminergic function. Compound 15 (DuP 734) is a combined antagonist of sigma-1 and serotonin 5HT(2) receptors, which has been entered into phase I clinical trials as a potential antipsychotic drug. Tetralins 1 and 2 were prepared to determine whether restriction of the conformation of 15 and its analogs may lead to differences in binding selectivity or in vivo profile. The syntheses and the structure-activity relationships of these compounds are reported herein. A reduced derivative, 14, had high affinity for sigma-1 and serotonin 5HT(2) receptors as well as excellent oral activity in some animal antipsychotic models. Furthermore, compound 14 failed to cause catalepsy in the rat up to 90 mg/kg (po).

  DOI：

  10.1021/jm00029a008
• 作为产物：
  描述：

  4-吡啶乙酸乙酯 在 sodium hydroxide 、 PPA 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 47.5h， 生成 2-(4-pyridinyl)tetralone
  参考文献：
  名称：

  Piperidinyltetralin .sigma. Ligands

  摘要：

  sigma receptor ligands have been proposed to be potential antipsychotic drugs based on their activity profile in animal behavioral models and their indirect modulation of dopaminergic function. Compound 15 (DuP 734) is a combined antagonist of sigma-1 and serotonin 5HT(2) receptors, which has been entered into phase I clinical trials as a potential antipsychotic drug. Tetralins 1 and 2 were prepared to determine whether restriction of the conformation of 15 and its analogs may lead to differences in binding selectivity or in vivo profile. The syntheses and the structure-activity relationships of these compounds are reported herein. A reduced derivative, 14, had high affinity for sigma-1 and serotonin 5HT(2) receptors as well as excellent oral activity in some animal antipsychotic models. Furthermore, compound 14 failed to cause catalepsy in the rat up to 90 mg/kg (po).

  DOI：

  10.1021/jm00029a008

文献信息

• Pyridyl-Substituierte Tetralonderivate: Eine Neue Klasse Nichtsteroidaler Aromatase-Inhibitoren
  作者：Herbert Bayer、Rolf W. Hartmann

  DOI：10.1002/ardp.2503241008

  日期：——

  Aromatase‐inhibitorischer Wirkung, wurden die Verbindungen 1‐7 synthetisiert und auf ihre Hemmaktivität gegenüber Aromatase und Desmolase unlersucht. Mit Ausnahme von Verbindung 2 zeigen alle Derivate eine stärkere Aromatase‐Hemmung als die Ausgangsverbindungen und erweisen sich auch als potentere Aromatase‐Inhibitoren als Aminoglutethimid (AG), der einzige im Handel befindliche Wirkstoff. Im Gegensatz

  以黄酮和黄烷酮这两种具有弱芳香化酶抑制作用的天然产物为原料，合成了化合物1-7，并研究了它们对芳香化酶和解链酶的抑制活性。除化合物 2 外，所有衍生物均显示出比起始化合物更强的芳香化酶抑制作用，并且证明是比市场上唯一的活性成分氨基鲁米特 (AG) 更有效的芳香化酶抑制剂。与 AG 相比，化合物 1 和 3-7 没有显示出对解糖酶的抑制，这会导致 AG 出现不良副作用。
• Bicyclic amides as inhibitors of acyl-coenzyme a: cholesterol acyl transferase
  申请人：SCHERING CORPORATION

  公开号：EP0508425A1

  公开（公告）日：1992-10-14

  Novel bicyclic amides of the formula wherein Ar¹ and Ar² are phenyl, R²-substituted phenyl, heteroaryl or R²-substituted heteroaryl, wherein R² is 1 to 3 substituents independently selected from the group consisting of halogeno, hydroxy, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and lower dialkylamino;    X, Y and Z are -CH₂-, -CH(alkyl)-, -C(alkyl)₂-, -NH-, -N(alkyl)-, -O- or SOr, wherein r is 0, 1 or 2, and m, n and p are 0 or 1;    R¹ is an alkyl chain of 1 to 25 carbon atoms; an alkyl chain substituted by one or more optionally substituted phenyl or heteroaryl groups; an alkyl chain -O-, -SOr, phenylene, R²-substituted phenylene, heteroarylene or R²-substituted heteroarylene groups; an interrupted alkyl chain substituted by one or more optionally substituted phenyl or heteroaryl groups; an alkyl chain of 4 to 25 carbon atoms, interrupted by one or more -NH-, -C(O)- or -N(lower alkyl)- groups; an interrupted alkyl chain of 4 to 25 carbon atoms substituted by one or more phenyl, R²-substituted phenyl, heteroaryl or R²-substituted heteroaryl groups; a diphenylamino group; a di-(R²-substituted phenyl)amino group; a diheteroarylamino group; or a di-(R²-substituted heteroaryl)amino group;    or a pharmaceutically acceptable salt thereof, useful in the treatment of artherosclerosis are disclosed.

  式中的新颖双环酰胺 其中 Ar¹ 和 Ar² 是苯基、R² 取代的苯基、杂芳基或 R² 取代的杂芳基，其中 R² 是 1 至 3 个取代基，这些取代基独立选自卤素、羟基、低级烷基、低级烷氧基、硝基、氨基、低级烷基氨基和低级二烷基氨基组成的组； X、Y 和 Z 是-CH₂-、-CH(烷基)-、-C(烷基)₂-、-NH-、-N(烷基)-、-O- 或 SOr，其中 r 是 0、1 或 2，m、n 和 p 是 0 或 1； R¹是 1 至 25 个碳原子的烷基链；被一个或多个任选取代的苯基或杂芳基取代的烷基链；-O-、-SOr、亚苯基、R²-取代的亚苯基、杂芳基或 R²-取代的杂芳基的烷基链；被一个或多个任选取代的苯基或杂芳基取代的间断烷基链；被一个或多个-NH-、-C(O)-或-N(低级烷基)-基团间断的 4 至 25 个碳原子的烷基链； 被一个或多个苯基、R²-取代的苯基、杂芳基或 R²-取代的杂芳基取代的 4 至 25 个碳原子的间断烷基链；二苯氨基基团；二(R²-取代苯基)氨基基团；二杂芳基氨基基团；或二(R²-取代杂芳基)氨基基团； 或其药学上可接受的盐，用于治疗动脉硬化。
• Inhibitors of Acyl CoA:Cholesterol Acyltransferase
  作者：Wayne Vaccaro、Cindy Amore、Joel Berger、Robert Burrier、John Clader、Harry Davis、Martin Domalski、Tom Fevig、Brian Salisbury、Rosy Sher

  DOI：10.1021/jm950833d

  日期：1996.1.1

  Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4-Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the mo st potent ACAT inhibitor identified (IC50 = 0.04 mu M in an in vitro rat hepatic microsomal ACAT assay, ED(50) = 0.72 mg/kg/day in cholesterol-fed hamsters).
• Gilligan Paul J., Kergaye Ahmed A., Lewis Bryan M., McElroy John F., J. Med. Chem, 37 (1994) N 3, S 364-370
  作者：Gilligan Paul J., Kergaye Ahmed A., Lewis Bryan M., McElroy John F.

  DOI：——

  日期：——
• BICYCLIC AMIDES AS INHIBITORS OF ACYL-COENZYME A: CHOLESTEROL ACYL TRANSFERASE
  申请人：SCHERING CORPORATION

  公开号：EP0583346A1

  公开（公告）日：1994-02-23