1-(5'-fluoro-2'-methoxyphenyl)-4,4-ethylenedioxybutyraldehyde | 878661-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(5'-fluoro-2'-methoxyphenyl)-4,4-ethylenedioxybutyraldehyde
• 英文别名: 4-(5'-fluoro-2'-methoxyphenyl)butyraldehyde；4-(5-Fluoro-2-methoxyphenyl)butanal
• CAS: 878661-35-9
• 化学式: C₁₁H₁₃FO₂
• 分子量: 196.221
• InChiKey: GMSNWZQQHUPGEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5'-fluoro-2'-methoxyphenyl)-4,4-ethylenedioxybutyraldehyde 、 (E/Z)-1-butenylmagnesium bromide 以 四氢呋喃 为溶剂， 反应 0.08h， 以61%的产率得到8-(5'-fluoro-2'-methoxyphenyl)oct-1-en-5-ol
  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：

  ethyl-4-(5'-fluoro-2'-methoxyphenyl)butyrate 在 二异丁基氢化铝 、 甲醇 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到1-(5'-fluoro-2'-methoxyphenyl)-4,4-ethylenedioxybutyraldehyde
  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

文献信息

• 2,5-Disubstituted tetrahydrofurans as selective serotonin re-uptake inhibitors
  作者：Troy Voelker、Haiji Xia、Keith Fandrick、Robert Johnson、Aaron Janowsky、John R. Cashman

  DOI：10.1016/j.bmc.2009.01.023

  日期：2009.3

  were prepared based on (−)-cocaine and aryltropanes as lead compounds because they are reasonably potent 5-HT re-uptake inhibitors. Molecular dissection of an aryltropane provided a series of 5- and 6-membered ring compounds. From among this library of compounds a series of disubstituted tetrahydrofurans bearing 2-alkyl aryl and 5-alkyl amino groups were identified as having highly potent and selective

  5-羟色胺（5-HT，5-羟色胺）神经传递的增强是治疗抑郁症的可行方法。基于该观察结果，基于（-）-可卡因和芳基环烷类作为先导化合物，制备了抑制5-HT再摄取的药物，因为它们是有效的5-HT再摄取抑制剂。芳基托烷的分子分解提供了一系列的5元和6元环化合物。从该化合物库中，鉴定出一系列带有2-烷基芳基和5-烷基氨基的二取代四氢呋喃具有高度有效和选择性的5-HT再摄取抑制作用。评价化合物与放射性标记的RTI-55结合竞争的能力以及在人多巴胺，5-羟色胺和去甲肾上腺素转运蛋白上抑制神经递质再摄取的能力。基于效力（例如，K i  = 800 pM）和显着的功能选择性（例如，人多巴胺：5-羟色胺或去甲肾上腺素：5-羟色胺的IC 50比，⩾1397）被确定为高效和选择性的5-羟色胺再摄取抑制剂。在结合亲和力和再摄取抑制中起主要作用的最佳特征包括芳族部分上的亲脂取代，反式2,5-二取代的四氢呋喃环的相对
• 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：Human BioMolecular Research Institute

  公开号：US08168635B2

  公开（公告）日：2012-05-01

  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.

  本发明涉及一种具有药理活性的制剂，可用于靶向细胞受体和细胞内信号通路，特别是中枢神经系统（CNS）神经递质的受体和信号通路。同时，本发明还涉及使用该制剂进行疾病或障碍的治疗或预防的相关方法和组合物。
• 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。
• Dual Inhibitors of Phosphodiesterase-4 and Serotonin Reuptake
  作者：John R. Cashman、Troy Voelker、Han-Ting Zhang、James M. O’Donnell

  DOI：10.1021/jm8010993

  日期：2009.3.26

  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.