2-((4-bromophenylthio)methyl)tetrahydro-2H-pyran | 1356207-07-2

• 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-((4-bromophenylthio)methyl)tetrahydro-2H-pyran
• 英文别名: 2-[(4-Bromophenyl)sulfanylmethyl]oxane；2-[(4-bromophenyl)sulfanylmethyl]oxane
• CAS: 1356207-07-2
• 化学式: C₁₂H₁₅BrOS
• 分子量: 287.221
• InChiKey: JYWHUUSACOAOJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 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：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((4-bromophenylthio)methyl)tetrahydro-2H-pyran 在 oxone(R) 作用下， 以 四氢呋喃 、 水 为溶剂， 以95%的产率得到2-((4-bromophenylsulfonyl)methyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)

  摘要：

  The design of a new clinical candidate histamine-H-3 receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl-R-2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with a sulfone. One compound from this series, 2j (APD916) increased wakefulness in rodents as measured by polysomnography with a duration of effect consistent with its pharmacokinetic properties. The identification of a suitable salt form of 2j allowed it to be selected for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.075
• 作为产物：
  描述：

  2-(bromomethyl)tetrahydro-2H-pyran 、 4-溴苯硫酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.0h， 以99%的产率得到2-((4-bromophenylthio)methyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)

  摘要：

  The design of a new clinical candidate histamine-H-3 receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl-R-2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with a sulfone. One compound from this series, 2j (APD916) increased wakefulness in rodents as measured by polysomnography with a duration of effect consistent with its pharmacokinetic properties. The identification of a suitable salt form of 2j allowed it to be selected for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.075

文献信息

• Identification of biaryl sulfone derivatives as antagonists of the histamine H3 receptor: Discovery of (R)-1-(2-(4′-(3-methoxypropylsulfonyl)biphenyl-4-yl)ethyl)-2-methylpyrrolidine (APD916)
  作者：Graeme Semple、Vincent J. Santora、Jeffrey M. Smith、Jonathan A. Covel、Rena Hayashi、Charlemagne Gallardo、Jason B. Ibarra、Jeffrey A. Schultz、Douglas M. Park、Scott A. Estrada、Brian J. Hofilena、Brian M. Smith、Albert Ren、Marissa Suarez、John Frazer、Jeffrey E. Edwards、Ryan Hart、Erin K. Hauser、Jodie Lorea、Andrew J. Grottick

  DOI：10.1016/j.bmcl.2011.11.075

  日期：2012.1

  The design of a new clinical candidate histamine-H-3 receptor antagonist for the potential treatment of excessive daytime sleepiness (EDS) is described. Phenethyl-R-2-methylpyrrolidine containing biphenylsulfonamide compounds were modified by replacement of the sulfonamide linkage with a sulfone. One compound from this series, 2j (APD916) increased wakefulness in rodents as measured by polysomnography with a duration of effect consistent with its pharmacokinetic properties. The identification of a suitable salt form of 2j allowed it to be selected for further development. (C) 2011 Elsevier Ltd. All rights reserved.