3-[3-(环戊氧基)-4-甲氧基苯基]丙酸 | 133332-30-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-[3-(环戊氧基)-4-甲氧基苯基]丙酸
• 英文名称: 3-[3-(cyclopentyloxy)-4-methoxyphenyl]propanoic acid
• 英文别名: 3-(3-Cyclopentoxy-4-methoxyphenyl)-n-propanoic acid；3-(3-Cyclopentyloxy-4-methoxyphenyl)propanoic acid
• CAS: 133332-30-6
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: CCVPUIBZJMOZCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-二甲基吗啉 、 3-[3-(环戊氧基)-4-甲氧基苯基]丙酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以44.3%的产率得到4-{3-[3-(cyclopentyloxy)-4-methoxyphenyl]propanoyl}-2,6-dimethylmorpholine
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of New 3-(Cyclopentyloxy)-4-methoxybenzaldehyde O-(2-(2,6-Dimethylmorpholino)-2-oxoethyl) Oxime (GEBR-7b) Related Phosphodiesterase 4D (PDE4D) Inhibitors

  摘要：

  A new series of 3-(cyclopentyloxy)-4-methoxyphenyl derivatives, structurally related to our hit GEBR-4a (1) and GEBR-7b (2), has been designed by changing length and functionality of the chain linking the catecholic moiety to the terminal cycloamine portion. Among the numerous molecules synthesized, compounds 8, 10a, and 10b showed increased potency as PDE4D enzyme inhibitors with respect to 2 and a good selectivity against PDE4A4, PDE4B2, and PDE4C2 enzymes, without both cytotoxic and genotoxic effects. The ability to enhance cAMP level in neuronal cells was assessed for compound 8. SAR considerations, also confirmed by in silico docking simulations, evidenced that both chain and amino terminal function characterized by higher hydrophilicity are required for a good and selective inhibitor-catalytic pocket interaction.

  DOI：

  10.1021/jm500855w
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 二甲氧基乙烷 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 3-[3-(环戊氧基)-4-甲氧基苯基]丙酸
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of New 3-(Cyclopentyloxy)-4-methoxybenzaldehyde O-(2-(2,6-Dimethylmorpholino)-2-oxoethyl) Oxime (GEBR-7b) Related Phosphodiesterase 4D (PDE4D) Inhibitors

  摘要：

  A new series of 3-(cyclopentyloxy)-4-methoxyphenyl derivatives, structurally related to our hit GEBR-4a (1) and GEBR-7b (2), has been designed by changing length and functionality of the chain linking the catecholic moiety to the terminal cycloamine portion. Among the numerous molecules synthesized, compounds 8, 10a, and 10b showed increased potency as PDE4D enzyme inhibitors with respect to 2 and a good selectivity against PDE4A4, PDE4B2, and PDE4C2 enzymes, without both cytotoxic and genotoxic effects. The ability to enhance cAMP level in neuronal cells was assessed for compound 8. SAR considerations, also confirmed by in silico docking simulations, evidenced that both chain and amino terminal function characterized by higher hydrophilicity are required for a good and selective inhibitor-catalytic pocket interaction.

  DOI：

  10.1021/jm500855w

文献信息

• Trisubstituted phenyl analogs having activity for congestive heart
  申请人：Warner-Lambert Company

  公开号：US04971959A1

  公开（公告）日：1990-11-20

  Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.

  新型的三取代苯类类似物现在被发现具有治疗充血性心力衰竭的活性。
• US4971959A
  申请人：——

  公开号：US4971959A

  公开（公告）日：1990-11-20
• US5274002A
  申请人：——

  公开号：US5274002A

  公开（公告）日：1993-12-28