5-methyl-2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1,3-phenylene diacetate | 1434878-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-methyl-2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1,3-phenylene diacetate
• 英文别名: [3-acetyloxy-5-methyl-2-(3-oxo-1H-2-benzofuran-1-yl)phenyl] acetate
• CAS: 1434878-87-1
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: OGAAXOPZCUWYMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-hydroxy-4-methyl-6-oxo-1-cyclohexen-1-yl)-3H-isobenzofuran-1-one 在 4-二甲氨基吡啶 、 mercury(II) diacetate 、 sodium acetate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 17.25h， 生成 5-methyl-2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1,3-phenylene diacetate
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones

  摘要：

  通过缩合、芳构化和乙酰化反应合成了系列十三种C-3功能化的异苯并呋喃-1(3H)-酮（苯酞类）。核磁共振（一维和二维实验）、红外光谱和质谱分析证实了合成化合物的身份。这些物质通过MTT细胞毒性试验在体外对U937（淋巴瘤）和K562（髓性白血病）癌细胞系进行了生物活性测试。某些衍生物在100 µM浓度下抑制了90%的细胞存活率。此外，两种苯酞类化合物显示出比依托泊苷（VP16）更强的生物活性，依托泊苷是一种在试验中用作阳性对照的商用药物。计算了所评估化合物的计算机模拟药物性质，并讨论了结果。

  DOI：

  10.3390/molecules18021881

文献信息

• Synthetic Analogues of the Natural Compound Cryphonectric Acid Interfere with Photosynthetic Machinery through Two Different Mechanisms
  作者：Róbson Ricardo Teixeira、Wagner Luiz Pereira、Deborah Campos Tomaz、Fabrício Marques de Oliveira、Samuele Giberti、Giuseppe Forlani

  DOI：10.1021/jf400698j

  日期：2013.6.12

  A series of isobenzofuran-1(3H)-ones (phthalides), analogues of the naturally occurring phytotoxin cryphonectric acid, were designed, synthesized, and fully characterized by NMR, IR, and MS analyses. Their synthesis was achieved via condensation, aromatization, and acetylation reactions. The measurement of the electron transport chain in spinach chloroplasts showed that several derivatives are capable of interfering with the photosynthetic apparatus. Few of them were found to inhibit the basal rate, but a significant inhibition was brought about only at concentrations exceeding 50 mu M. Some other analogues acted as uncouplers or energy transfer inhibitors, with a remarkably higher effectiveness. Isobenzofuranone addition to the culture medium inhibited the growth of the cyanobacterium,Synechococcus elongatus, with patterns consistent with the effects measured in vitro upon isolated chloroplasts. The most active derivatives, being able to completely suppress algal growth at 20 mu M, may represent structures to be exploited for the design of new active ingredients for weed control.