Methyl 3-(4-decoxyphenyl)propanoate | 126148-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 3-(4-decoxyphenyl)propanoate
• CAS: 126148-71-8
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: DIYJAGZLFZANFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-(4-decoxyphenyl)propanoate 在 甲醇 、 sodium hydroxide 作用下， 反应 12.0h， 生成 3-<4-Decyloxy-phenyl>-propionsaeure
  参考文献：
  名称：

  Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes

  摘要：

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.

  DOI：

  10.1021/jm800649q
• 作为产物：
  描述：

  methyl (E)-3-(4-decyloxy-phenyl)-acrylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 Methyl 3-(4-decoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes

  摘要：

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.

  DOI：

  10.1021/jm800649q

文献信息

• Sebosuppressive topische Zubereitungen
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0315914A2

  公开（公告）日：1989-05-17

  Alkyl-arylether-Derivate der Formel (1) in der R¹ eine einfach oder mehrfach verzweigte Alkygruppe mit 8 - 20 C-Atomen, E eine Gruppe -CH₂-CH₂- oder -CH = CH- und R² eine Alkylgruppe mit 1 - 4 C-Atomen, eine Hydroxyalkyl­gruppe mit 2 - 4 C-Atomen, eine Alkoxyalkylgruppe, Wasserstoff oder ein salzbildenes Kation ist, eignen sich als sebosuppressive Wirkstoffe in kosmetischen oder pharmazeutischen Zubereitungen zur topischen Anwendung auf dem Haar und auf der Haut.

  式（1）的烷基芳基醚衍生物 其中 R¹ 是具有 8-20 个碳原子的单支链或多支链烷基，E 是基团-CH₂-CH₂- 或 -CH = CH-，R² 是具有 1-4 个碳原子的烷基、具有 2-4 个碳原子的羟烷基、烷氧基烷基、氢或成盐阳离子，这些衍生物可用作化妆品或药物制剂中的皮脂抑制活性成分，局部用于头发和皮肤。
• US4942174A
  申请人：——

  公开号：US4942174A

  公开（公告）日：1990-07-17
• Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes
  作者：Constantinos Baskakis、Victoria Magrioti、Naomi Cotton、Daren Stephens、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1021/jm800649q

  日期：2008.12.25

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.