toluene-4-sulfonic acid (1,2,3,4-tetrahydronaphthalen-2-ylmethyl) ester | 835871-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid (1,2,3,4-tetrahydronaphthalen-2-ylmethyl) ester
• 英文别名: (1,2,3,4-tetrahydronaphthalen-2-yl)methyl p-toluenesulfonate；1,2,3,4-tetrahydronaphthalen-2-ylmethyl 4-methylbenzenesulfonate
• CAS: 835871-96-0
• 化学式: C₁₈H₂₀O₃S
• 分子量: 316.421
• InChiKey: WBVFZYWSLLMVAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-苄基哌啶 、 toluene-4-sulfonic acid (1,2,3,4-tetrahydronaphthalen-2-ylmethyl) ester 以 甲苯 为溶剂， 反应 12.0h， 以82%的产率得到4-Benzyl-1-(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：

  1,2,3,4-tetrahydro-2-(hydroxymethylene)naphthalen-1-one 在 borane tert-butylamine complex 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 toluene-4-sulfonic acid (1,2,3,4-tetrahydronaphthalen-2-ylmethyl) ester
  参考文献：
  名称：

  Noaceptin / Orphanin FQ受体配体的Triazaspirodecanone衍生物的合成及其构效关系

  摘要：

  合成了几种螺索托林衍生物，并将其评估为潜在的NOP受体配体。螺氧杂环丁烷的1,4-苯并二恶烷部分的结构修饰一直是该研究项目的重点。出现的结构-活性关系表明，当H-键供体基团（羟基）相对于与1-苯基-1,3连接的CH 2处于α位置时，它更有利于NOP活性， 8-triaza-spiro [4.5] decan-4-一份。此外，羟基衍生物4和22的顺式非对映异构体显示出比反式异构体适度更高的立体选择性。尤其是螺哌啶衍生物cis - 4具有亚微摩尔激动活性，它将成为设计和合成新的NOP激动剂的参考化合物。

  DOI：

  10.1111/cbdd.12505

文献信息

• Pyrrolidine compounds and medicinal utilization thereof
  申请人：Mitsubishi Pharma Corporation

  公开号：US06468998B1

  公开（公告）日：2002-10-22

  The present invention provides a pyrrolidine compound of the formula (I) wherein each symbol is as defined in the specification, an optically active compound thereof and a pharmaceutically acceptable salt thereof. The present invention further provides a pharmaceutical composition containing a compound of the formula (I), an optically active compound thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive. The compound of the present invention has a serotonin 2 receptor antagonistic action along with a platelet aggregation suppressive action, a peripheral circulation improving action and a lacrimation promoting action. Therefore, the compound of the present invention can be a useful medicine showing effect against thrombotic embolism, dry eye and the like.

  本发明提供了一种式(I)的吡咯烷化合物，其中每个符号如规范中定义，以及其光学活性化合物和药学上可接受的盐。本发明还提供了一种含有式(I)的化合物、其光学活性化合物或药学上可接受的盐以及药学上可接受的添加剂的药物组合物。本发明的化合物具有血清素2受体拮抗作用，同时具有抑制血小板聚集、改善外周循环和促进泪液分泌的作用。因此，本发明的化合物可以是一种有益的药物，对抗血栓栓塞、干眼症等具有一定效果。
• PYRROLIDINE COMPOUNDS AND MEDICINAL UTILIZATION THEREOF
  申请人：Welfide Corporation

  公开号：EP1125922A1

  公开（公告）日：2001-08-22

  The present invention provides a pyrrolidine compound of the formula (I) wherein each symbol is as defined in the specification, an optically active compound thereof and a pharmaceutically acceptable salt thereof. The present invention further provides a pharmaceutical composition containing a compound of the formula (I), an optically active compound thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive. The compound of the present invention has a serotonin 2 receptor antagonistic action along with a platelet aggregation suppressive action, a peripheral circulation improving action and a lacrimation promoting action. Therefore, the compound of the present invention can be a useful medicine showing effect against thrombotic embolism, dry eye and the like.

  本发明提供了一种式 (I) 的吡咯烷化合物 其中各符号如说明书中所定义，其光学活性化合物及其药学上可接受的盐。本发明进一步提供了含有式（I）化合物、其光学活性化合物或其药学上可接受的盐以及药学上可接受的添加剂的药物组合物。本发明的化合物具有 5-羟色胺 2 受体拮抗作用、血小板聚集抑制作用、外周循环改善作用和流泪促进作用。因此，本发明的化合物可以作为一种有用的药物，对血栓性栓塞、干眼症等具有疗效。
• US6468998B1
  申请人：——

  公开号：US6468998B1

  公开（公告）日：2002-10-22
• 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.
• Synthesis and Structure-Activity Relationships of Triazaspirodecanone Derivatives as Nociceptin/Orphanin FQ Receptor Ligands
  作者：Sandra Corrado、Umberto M. Battisti、Claudia Sorbi、Annalisa Tait、Davide Malfacini、Valeria Camarda、Girolamo Calò、Livio Brasili

  DOI：10.1111/cbdd.12505

  日期：2015.10

  to the CH2 linked to the 1‐phenyl‐1,3,8‐triaza‐spiro[4.5]decan‐4‐one portion. Moreover, cis diastereoisomers of the hydroxyl derivatives4 and 22 show a moderately higher degree of stereoselectivity than trans isomers. In particular, the spiropiperidine derivative cis‐4 has submicromolar agonistic activity, and it will be the reference compound for the design and synthesis of new NOP agonists.

  合成了几种螺索托林衍生物，并将其评估为潜在的NOP受体配体。螺氧杂环丁烷的1,4-苯并二恶烷部分的结构修饰一直是该研究项目的重点。出现的结构-活性关系表明，当H-键供体基团（羟基）相对于与1-苯基-1,3连接的CH 2处于α位置时，它更有利于NOP活性， 8-triaza-spiro [4.5] decan-4-一份。此外，羟基衍生物4和22的顺式非对映异构体显示出比反式异构体适度更高的立体选择性。尤其是螺哌啶衍生物cis - 4具有亚微摩尔激动活性，它将成为设计和合成新的NOP激动剂的参考化合物。