(2-butin-1-yl)acetylsalicylate | 300407-65-2

• 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-butin-1-yl)acetylsalicylate
• 英文别名: (but-2-ynyl)-2-acetoxybenzoate；But-ASS；But-2-ynyl 2-acetoxybenzoate；but-2-ynyl 2-acetyloxybenzoate
• CAS: 300407-65-2
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: PAQABXKMCYMUHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dicobalt octacarbonyl 、 (2-butin-1-yl)acetylsalicylate 以 四氢呋喃 为溶剂， 以35%的产率得到[(2-butin-1-yl)acetylsalicylate]hexacarbonyldicobalt
  参考文献：
  名称：

  Acetylenehexacarbonyldicobalt complexes, a novel class of antitumor drugs

  摘要：

  Acetylenehexacarbonyldicobalt bait complexes were synthesized and tested for antitumor activity. The MCF-7 and MDA-MB-231 mammary tumor cell lines and the LNCaP/FGC prostate carcinoma cell line were used as in vitro models. The structural evaluation was performed by IR and NMR spectroscopy and revealed a change of the linear acetylene core to a structure comparable to Z-olefins after coordination to the cobalt centers. In cell culture experiments the strongest effects were found for hexacarbonyl[2-propinylacetylsalicylate] (10), which was more active than cisplatin on the human mammary tumor cell lines MCF-7 and MDA-MB-231 in each concentration tested (a 5 mu M concentration of this compound even caused cytocidal effects). In contrast to this, 10 influenced the growth of the LNCaP/FGC cells only marginally, even in the highest concentration. The mode of action of the complexes tested is unknown. As the cobalt complexes show strong antiproliferative effects and their ligands do not it could be unambiguously demonstrated that complex formation is essential to achieve cytotoxic effects. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00139-0
• 作为产物：
  描述：

  2-丁炔-1-醇 、 邻乙酰水杨酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 以89%的产率得到(2-butin-1-yl)acetylsalicylate
  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

文献信息

• Synthesis and Biological Activities of Transition Metal Complexes Based on Acetylsalicylic Acid as Neo-Anticancer Agents
  作者：Gerhard Rubner、Kerstin Bensdorf、Anja Wellner、Brigitte Kircher、Silke Bergemann、Ingo Ott、Ronald Gust

  DOI：10.1021/jm101019j

  日期：2010.10.14

  [(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.
• Acetylenehexacarbonyldicobalt complexes, a novel class of antitumor drugs
  作者：Kathrin Schmidt、Manfred Jung、Roland Keilitz、Beate Schnurr、Ronald Gust

  DOI：10.1016/s0020-1693(00)00139-0

  日期：2000.8

  Acetylenehexacarbonyldicobalt bait complexes were synthesized and tested for antitumor activity. The MCF-7 and MDA-MB-231 mammary tumor cell lines and the LNCaP/FGC prostate carcinoma cell line were used as in vitro models. The structural evaluation was performed by IR and NMR spectroscopy and revealed a change of the linear acetylene core to a structure comparable to Z-olefins after coordination to the cobalt centers. In cell culture experiments the strongest effects were found for hexacarbonyl[2-propinylacetylsalicylate] (10), which was more active than cisplatin on the human mammary tumor cell lines MCF-7 and MDA-MB-231 in each concentration tested (a 5 mu M concentration of this compound even caused cytocidal effects). In contrast to this, 10 influenced the growth of the LNCaP/FGC cells only marginally, even in the highest concentration. The mode of action of the complexes tested is unknown. As the cobalt complexes show strong antiproliferative effects and their ligands do not it could be unambiguously demonstrated that complex formation is essential to achieve cytotoxic effects. (C) 2000 Elsevier Science S.A. All rights reserved.