Pentadiene-ASS | 1251105-54-0

• 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: Pentadiene-ASS
• 英文别名: ((Z)-penta-2,4-dienyl)-2-acetoxybenzoate
• CAS: 1251105-54-0
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: OBCZNQVNRVPCER-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,4-pentadien-1-ol 、 邻乙酰水杨酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 以37%的产率得到((E)-penta-2,4-dienyl)-2-acetoxybenzoate
  参考文献：
  名称：

  Synthesis and Biological Activities of Transition Metal Complexes Based on Acetylsalicylic Acid as Neo-Anticancer Agents

  摘要：

  [(mu(4)-(eta(2))-(Prop-2-ynyl)-2-acetoxybenzoate]dicobalthexacarbonyl (Co-ASS). a derivative of aspirin (ASS). demonstrated high growth-inhibitory potential against various tumor cells with interference in the arachidonic acid cascade as probable mode of action. The significance of the kind of metal and cluster was verified in this structure activity study: Co(2)(CO)(6) was respectively exchanged by a tin rameric cobalttrimeric ruthenium-, or trimeric ironcarbonyl cluster. Furthermore, the metal binding motif was changed from alkyne to 1,3-butadiene. Compounds were evaluated For growth inhibition, antiproliferative effects. and apoptosis induction in breast (MCF-7. MDA-MB 231) and colon cancer (HT-29) cell lines and for COX-1/2 inhibitory effects at isolated isoenzymes. Additionally, the major COX metabolite prostaglandin (PGE(2)) was quantified in arachidonic acid-stimulated MDA-MB 231 breast tumor cells. It was demonstrated that the metal cluster was of minor importance for abets on cellular activity if an alkyne was used as ligand. Generally, no correlation existed between growth inhibition and COX activity. Cellular growth inhibition and antiproliferative activity at higher concentrations of the most active compounds Prop-ASS-Co(4) and Prop-ASS-Ru(3) correlated well with apoptosis induction.

  DOI：

  10.1021/jm101019j