1-[(3-cyclopentyloxy-4-methoxyphenyl)methylideneamino]oxy-3-morpholin-4-ylpropan-2-ol | 685558-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(3-cyclopentyloxy-4-methoxyphenyl)methylideneamino]oxy-3-morpholin-4-ylpropan-2-ol
• CAS: 685558-49-0
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: QQPQPLHZCIULFX-UHFFFAOYSA-N

物化性质

• 沸点：
  215-220 °C(Press: 0.4 Torr)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.75
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-[(3-cyclopentyloxy-4-methoxyphenyl)methylideneamino]oxy-3-morpholin-4-ylpropan-2-ol 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到3-(cyclopentyloxy)-4-methoxybenzaldehyde O-[2-chloro-3-(morpholin-4yl)propyl]oxime
  参考文献：
  名称：

  New Selective Phosphodiesterase 4D Inhibitors Differently Acting on Long, Short, and Supershort Isoforms

  摘要：

  The lack of selective inhibitors toward the long, short, or supershort phosphodiesterases (PDE4s) prevented researchers from carefully defining the connection between different enzyme isoforms, their brain localization, and their role in neurodegenerative diseases such as Alzheimer's disease (AD). In the search for new therapeutic agents for treating memory and learning disorders, we synthesized new rolipram related PDE4 inhibitors, which had sonic selectivity toward the long form PDE4D3. The first series was synthesized as racemate and then resolved by semipreparative HPLC on chiral supports. Herein we report the synthetic pathways to obtain compounds 1a-c, 2a-c, 3a-c, 4a-f, 5a,b, 6a,b, 7a,b, the chiral analytical study to resolve compounds la-c, 2a-c, 3a-c, the molecular docking Study for compound 1c, and the biological results and sonic SAR considerations that provide sonic insights and hints for the structural requirements for PDE4D Subtype selectivity and enzyme inhibition.

  DOI：

  10.1021/jm900977c
• 作为产物：
  描述：

  吗啉 、 3-(cyclopentyloxy)-4-methoxybenzaldehyde O-(oxiran-2-ylmethyl)oxime 反应 18.0h， 生成 1-[(3-cyclopentyloxy-4-methoxyphenyl)methylideneamino]oxy-3-morpholin-4-ylpropan-2-ol
  参考文献：
  名称：

  New Selective Phosphodiesterase 4D Inhibitors Differently Acting on Long, Short, and Supershort Isoforms

  摘要：

  The lack of selective inhibitors toward the long, short, or supershort phosphodiesterases (PDE4s) prevented researchers from carefully defining the connection between different enzyme isoforms, their brain localization, and their role in neurodegenerative diseases such as Alzheimer's disease (AD). In the search for new therapeutic agents for treating memory and learning disorders, we synthesized new rolipram related PDE4 inhibitors, which had sonic selectivity toward the long form PDE4D3. The first series was synthesized as racemate and then resolved by semipreparative HPLC on chiral supports. Herein we report the synthetic pathways to obtain compounds 1a-c, 2a-c, 3a-c, 4a-f, 5a,b, 6a,b, 7a,b, the chiral analytical study to resolve compounds la-c, 2a-c, 3a-c, the molecular docking Study for compound 1c, and the biological results and sonic SAR considerations that provide sonic insights and hints for the structural requirements for PDE4D Subtype selectivity and enzyme inhibition.

  DOI：

  10.1021/jm900977c

文献信息

• New Selective Phosphodiesterase 4D Inhibitors Differently Acting on Long, Short, and Supershort Isoforms
  作者：Olga Bruno、Alessia Romussi、Andrea Spallarossa、Chiara Brullo、Silvia Schenone、Francesco Bondavalli、Nicolas Vanthuyne、Christian Roussel

  DOI：10.1021/jm900977c

  日期：2009.11.12

  The lack of selective inhibitors toward the long, short, or supershort phosphodiesterases (PDE4s) prevented researchers from carefully defining the connection between different enzyme isoforms, their brain localization, and their role in neurodegenerative diseases such as Alzheimer's disease (AD). In the search for new therapeutic agents for treating memory and learning disorders, we synthesized new rolipram related PDE4 inhibitors, which had sonic selectivity toward the long form PDE4D3. The first series was synthesized as racemate and then resolved by semipreparative HPLC on chiral supports. Herein we report the synthetic pathways to obtain compounds 1a-c, 2a-c, 3a-c, 4a-f, 5a,b, 6a,b, 7a,b, the chiral analytical study to resolve compounds la-c, 2a-c, 3a-c, the molecular docking Study for compound 1c, and the biological results and sonic SAR considerations that provide sonic insights and hints for the structural requirements for PDE4D Subtype selectivity and enzyme inhibition.