2-bromo-4-methyl-1-p-tolylsulfanylbenzene | 1293343-29-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-bromo-4-methyl-1-p-tolylsulfanylbenzene
• 英文别名: 1-bromo-2-(4-methyl-phenylsulfanyl)-5-methyl-benzene；2-bromo-4-methyl-1-(4-methylphenyl)sulfanylbenzene
• CAS: 1293343-29-9
• 化学式: C₁₄H₁₃BrS
• 分子量: 293.227
• InChiKey: BWEQYCDATZHYAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-4-methyl-1-p-tolylsulfanylbenzene 在 盐酸 、 甲醇 、 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 1-(5-methyl-2-p-tolylsulfanylphenyl)piperazine hydrochloride
  参考文献：
  名称：

  Discovery of 1-[2-(2,4-Dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): A Novel Multimodal Compound for the Treatment of Major Depressive Disorder

  摘要：

  The synthesis and structure-activity relationship of a novel series of compounds with combined effects on 5-HT3A and 5-HT1A receptors and on the serotonin (5-HT) transporter (SERT) are described. Compound 5m (Lu AA21004) was the lead compound, displaying high affinity for recombinant human 5-HT1A (K-i = 15 nM), 5-HT1B (K-i = 33 nM), 5-HT3A (K-i = 3.7 nM), 5-HT7 (K-i = 19 nM), and noradrenergic beta(1) (K-i = 46 nM) receptors, and SERT (K-i = 1.6 nM). Compound 5m displayed antagonistic properties at 5-HT3A and 5-HT7 receptors, partial agonist properties at 5-HT1B receptors, agonistic properties at 5-HT1A receptors, and potent inhibition of SERT. In conscious rats, 5m significantly increased extracellular 5-HT levels in the brain after acute and 3 days of treatment. Following the 3-day treatment (5 or 10 (mg/kg)/day) SERT occupancies were only 43% and 57%, respectively. These characteristics indicate that 5m is a novel multimodal serotonergic compound, and 5m is currently in clinical development for major depressive disorder.

  DOI：

  10.1021/jm101459g
• 作为产物：
  描述：

  3-溴-4-碘甲苯 、 4-甲苯硫酚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 双(2-二苯基磷苯基)醚 作用下， 以 甲苯 为溶剂， 生成 2-bromo-4-methyl-1-p-tolylsulfanylbenzene
  参考文献：
  名称：

  Discovery of 1-[2-(2,4-Dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): A Novel Multimodal Compound for the Treatment of Major Depressive Disorder

  摘要：

  The synthesis and structure-activity relationship of a novel series of compounds with combined effects on 5-HT3A and 5-HT1A receptors and on the serotonin (5-HT) transporter (SERT) are described. Compound 5m (Lu AA21004) was the lead compound, displaying high affinity for recombinant human 5-HT1A (K-i = 15 nM), 5-HT1B (K-i = 33 nM), 5-HT3A (K-i = 3.7 nM), 5-HT7 (K-i = 19 nM), and noradrenergic beta(1) (K-i = 46 nM) receptors, and SERT (K-i = 1.6 nM). Compound 5m displayed antagonistic properties at 5-HT3A and 5-HT7 receptors, partial agonist properties at 5-HT1B receptors, agonistic properties at 5-HT1A receptors, and potent inhibition of SERT. In conscious rats, 5m significantly increased extracellular 5-HT levels in the brain after acute and 3 days of treatment. Following the 3-day treatment (5 or 10 (mg/kg)/day) SERT occupancies were only 43% and 57%, respectively. These characteristics indicate that 5m is a novel multimodal serotonergic compound, and 5m is currently in clinical development for major depressive disorder.

  DOI：

  10.1021/jm101459g

文献信息

• [EN] 4-(2-PHENYLSULFANYL-PHENYL)-PIPERIDINE DERIVATIVES AS SEROTONIN REUPTAKE INHIBITORS<br/>[FR] DERIVES 4-(2-PHENYLSULFANYL-PHENYL)-PIPERIDINES UTILISES EN TANT QU'INHIBITEURS DE REABSORPTION DE LA SEROTONINE
  申请人：LUNDBECK & CO AS H

  公开号：WO2004087156A1

  公开（公告）日：2004-10-14

  The invention provides compounds represented by the general formula (I) wherein the substituents are defined in the application. The compounds are useful in the treatment of an affective disorder, including depression, anxiety disorders including general anxiety disorder and panic disorder and obsessive compulsive disorder.

  该发明提供了一种由一般公式（I）表示的化合物，其中取代基在申请中定义。这些化合物在治疗情感障碍方面具有用途，包括抑郁症、焦虑障碍（包括广泛性焦虑障碍和恐慌障碍）以及强迫症。
• 4-(2-Phenylsulfanyl-phenyl)-piperidine derivates as serotonin reuptake inhibitors
  申请人：Puschl Ask

  公开号：US20060100242A1

  公开（公告）日：2006-05-11

  The invention provides compounds represented by the general formula (I) wherein the substituents are defined in the application. The compounds are useful in the treatment of an affective disorder, including depression, anxiety disorders including general anxiety disorder and panic disorder and obsessive compulsive disorder.

  本发明提供了通式(I)表示的化合物，其中取代基在申请中定义。这些化合物可用于治疗情感障碍，包括抑郁症、焦虑障碍（包括普遍性焦虑障碍和恐慌障碍）和强迫症。
• 4-(2-phenylsulfanyl-phenyl)-piperidine derivatives as serotonin reuptake inhibitors
  申请人：H. Lundbeck A/S

  公开号：US07732463B2

  公开（公告）日：2010-06-08

  The invention provides compounds represented by the general formula (I) wherein the substituents are defined in the application. The compounds are useful in the treatment of an affective disorder, including depression, anxiety disorders including general anxiety disorder and panic disorder and obsessive compulsive disorder.

  该发明提供了通式（I）所表示的化合物，其中取代基在申请书中定义。该化合物在治疗情感障碍中很有用，包括抑郁症、焦虑障碍，包括广泛性焦虑障碍和恐慌障碍以及强迫症。
• 4-(2-PHENYLSULFANYL-PHENYL)-PIPERIDINE DERIVATIVES AS SEROTONIN REUPTAKE INHIBITORS
  申请人：H. LUNDBECK A/S

  公开号：EP1626720B1

  公开（公告）日：2008-09-03
• US7732463B2
  申请人：——

  公开号：US7732463B2

  公开（公告）日：2010-06-08