2-(bromomethyl)-5-(3'-(2''-methoxy-5''-fluorophenyl)-1'-propyl)tetrahydrofuran | 878661-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(bromomethyl)-5-(3'-(2''-methoxy-5''-fluorophenyl)-1'-propyl)tetrahydrofuran
• 英文别名: 2-(bromomethyl)-5-(2''-methoxy-5''-fluorophenyl-3'-propyl)tetrahydrofuran；2-(Bromomethyl)-5-[3-(5-fluoro-2-methoxyphenyl)propyl]oxolane
• CAS: 878661-42-8
• 化学式: C₁₅H₂₀BrFO₂
• 分子量: 331.225
• InChiKey: BOSMDQALBYRNND-UHFFFAOYSA-N

物化性质

• 沸点：
  390.0±27.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰化钾 、 2-(bromomethyl)-5-(3'-(2''-methoxy-5''-fluorophenyl)-1'-propyl)tetrahydrofuran 在 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以89%的产率得到cis-2-cyanomethyl-5-(3'-(2''-methoxy-5''-fluorophenyl)-1'-propyl)tetrahydrofuran
  参考文献：
  名称：

  [EN] MODULATORS OF CENTRAL NERVOUS SYSTEM NEUROTRANSMITTERS
  [FR] MODULATEURS DE NEUROTRANSMETTEURS DU SYSTEME NERVEUX CENTRAL

  摘要：

  公开号：

  WO2006025920A3
• 作为产物：
  描述：

  8-(5'-fluoro-2'-methoxyphenyl)oct-1-en-5-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到2-(bromomethyl)-5-(3'-(2''-methoxy-5''-fluorophenyl)-1'-propyl)tetrahydrofuran
  参考文献：
  名称：

  Dual Inhibitors of Phosphodiesterase-4 and Serotonin Reuptake

  摘要：

  A new class of multitarget compounds was synthesized by linking a novel selective serotonin reuptake inhibitor (SSRI) to a PDE4 inhibitor. The new dual PDE4 inhibitor/SSRI showed antidepressant-like activity in the forced swim test in mice The SSRIs 2-{5-[3-(5-fluoro-2-methoxy-phenyl)-ethyl]-tetrahydro-furan-2-yl}-ethylamine (14) and 2-{5-[3-(5-fluoro-2-methoxy-phenyl)-propyl]-tetrahydro-furan-2-yl}-ethylamine (15) were both individually linked to the PDE4 inhibitor 4-(3,4-dimethoxy-phenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one (19), via a five-carbon chain. The dual PDE4 inhibitor/SSRI 2-{5-[3-(5-fluoro-2-methoxyphenyl)-ethyl]-tetrahydro-furan-2-yl}-ethylamine)-pentyl]-4,5,8,8a-tetrahydro-2H-phthalazin-1-one (21) showed potent and selective serotonin reuptake inhibition (IC50 value of 127 nM). The dual PDE4 inhibitor/SSRI 21 also inhibited PDE4D3 with a K-i value of 2.0 nM. The dual PDE4 inhibitor/SSRI was significantly more effective than the individual SSRI alone or fluoxetine in the forced swim test at standard doses. On a molar basis, the antidepressant-like effect of the dual PDE4 inhibitor/SSRI 21 showed a 129-fold increase in in vivo efficacy compared to fluoxetine.

  DOI：

  10.1021/jm8010993

文献信息

• Modulators of Central Nervous System Neurotransmitters
  申请人：Cashman John

  公开号：US20080261967A1

  公开（公告）日：2008-10-23

  Disclosed are agents having pharmacological activity against cellular receptors and intracellular signaling, particularly receptors and signaling pathways of central nervous system (CNS) neurotransmitters. Also disclosed are related methods and compositions for the treatment or prevention of diseases or disorders using the agents.

  本发明涉及具有药理活性的药物，特别是针对细胞受体和细胞内信号传导的药物，尤其是中枢神经系统（CNS）神经递质的受体和信号通路。本发明还涉及使用这些药物的相关方法和组合物，用于治疗或预防疾病或障碍。
• MODULATORS OF CENTRAL NERVOUS SYSTEM NEUROTRANSMITTERS
  申请人：CASHMAN John

  公开号：US20130123253A1

  公开（公告）日：2013-05-16

  Disclosed are agents having pharmacological activity against cellular receptors and intracellular signaling, particularly receptors and signaling pathways of central nervous system (CNS) neurotransmitters. Also disclosed are related methods and compositions for the treatment or prevention of diseases or disorders using the agents.

  本发明涉及一种对细胞受体和细胞内信号传导具有药理活性的药剂，特别是针对中枢神经系统（CNS）神经递质的受体和信号通路。本发明还涉及使用这些药剂的相关方法和组合物，用于治疗或预防疾病或障碍。
• US8168635B2
  申请人：——

  公开号：US8168635B2

  公开（公告）日：2012-05-01