(2-[(4-methoxyphenoxy)methyl]-4-(methylethylidene)-5-oxo-2,3-dihydrofuryl)methyl 2-(4-[2-(4-methylphenyl)ethynyl]phenoxy)acetate | 1151816-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-[(4-methoxyphenoxy)methyl]-4-(methylethylidene)-5-oxo-2,3-dihydrofuryl)methyl 2-(4-[2-(4-methylphenyl)ethynyl]phenoxy)acetate
• 英文别名: [2-[(4-Methoxyphenoxy)methyl]-5-oxo-4-propan-2-ylideneoxolan-2-yl]methyl 2-[4-[2-(4-methylphenyl)ethynyl]phenoxy]acetate
• CAS: 1151816-89-5
• 化学式: C₃₃H₃₂O₇
• 分子量: 540.613
• InChiKey: XJLJNEHBJRKGHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-[(4-methoxyphenoxy)methyl]-4-(methylethylidene)-5-oxo-2,3-dihydrofuryl)methyl 2-(4-[2-(4-methylphenyl)ethynyl]phenoxy)acetate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以54%的产率得到[2-(hydroxymethyl)-4-(methylethylidene)-5-oxo-2,3-dihydrofuryl]methyl 2-(4-[2-(4-methylphenyl)ethynyl]phenoxy)acetate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 31. Modulation of the Biological Properties of Diacylgycerol Lactones (DAG-lactones) Containing Rigid-Rod Acyl Groups Separated from the Core Lactone by Spacer Units of Different Lengths

  摘要：

  Diacylglycerol lactones built with a rigid 4-[(methylphenyl)ethynyl]phenyl rod that is separated from the exocyclic acylcarbonyl of the DAG-lactone core by a spacer unit of variable length were synthesized and studied. Binding affinities for a panel of classical and novel PKC isozymes in two different phospholipid environments, one corresponding to the plasma membrane of cells, were determined. The kinetics and site of translocation for the PKC isozymes alpha and delta upon treatment with the compounds were also studied as well as the early response of ERK phosphorylation and the late response of induction of apoptosis in the human prostatic carcinoma cell line LNCaP. Finally, the compounds were evaluated in terms of their interaction with biomimetic lipid/polydiacetylene membranes by the associated chromatic response. The different spatial disposition of the rigid structural motif on the DAG-lactones contributes to differential activity.

  DOI：

  10.1021/jm900186m
• 作为产物：
  描述：

  5-(hydroxymethyl)-5-[(4-methoxyphenoxy)methyl]-3-(methylethylidene)-4,5-dihydrofuran-2-one 、 2-(4-(p-tolylethynyl)phenoxy)acetic acid 在 4-二甲氨基吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到(2-[(4-methoxyphenoxy)methyl]-4-(methylethylidene)-5-oxo-2,3-dihydrofuryl)methyl 2-(4-[2-(4-methylphenyl)ethynyl]phenoxy)acetate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 31. Modulation of the Biological Properties of Diacylgycerol Lactones (DAG-lactones) Containing Rigid-Rod Acyl Groups Separated from the Core Lactone by Spacer Units of Different Lengths

  摘要：

  Diacylglycerol lactones built with a rigid 4-[(methylphenyl)ethynyl]phenyl rod that is separated from the exocyclic acylcarbonyl of the DAG-lactone core by a spacer unit of variable length were synthesized and studied. Binding affinities for a panel of classical and novel PKC isozymes in two different phospholipid environments, one corresponding to the plasma membrane of cells, were determined. The kinetics and site of translocation for the PKC isozymes alpha and delta upon treatment with the compounds were also studied as well as the early response of ERK phosphorylation and the late response of induction of apoptosis in the human prostatic carcinoma cell line LNCaP. Finally, the compounds were evaluated in terms of their interaction with biomimetic lipid/polydiacetylene membranes by the associated chromatic response. The different spatial disposition of the rigid structural motif on the DAG-lactones contributes to differential activity.

  DOI：

  10.1021/jm900186m