3-(2-hydroxy-4-methyl-6-oxo-1-cyclohexen-1-yl)-3H-isobenzofuran-1-one | 959927-87-8

• 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: 3-(2-hydroxy-4-methyl-6-oxo-1-cyclohexen-1-yl)-3H-isobenzofuran-1-one
• 英文别名: 3-(2-hydroxy-4-methyl-6-oxocyclohex-1-en-1-yl)isobenzofuran-1(3H)-one；3-(2-hydroxy-4-methyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one；3-(2-hydroxy-4-methyl-6-oxocyclohexen-1-yl)-3H-2-benzofuran-1-one
• CAS: 959927-87-8
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: RVNRVEGLIMUPBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 、 邻羧基苯甲醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 3-(2-hydroxy-4-methyl-6-oxo-1-cyclohexen-1-yl)-3H-isobenzofuran-1-one
  参考文献：
  名称：

  异苯并呋喃-1(3H)-one 衍生物的酮-烯醇互变异构的核磁共振 (NMR)、红外 (IR) 和质谱 (MS) 研究

  摘要：

  摘要 3-(2-hydroxy-4,4-dimethyl-6-oxo-cyclohexen-1-yl)isobenzofuran-1(3H-one (1), 3-(2-hydroxy-6- oxocyclohex-1-enyl)isobenzofuran-1(3H)-one (2), 3-(2-hydroxy-4-methyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one (3), 3 -(2-hydroxy-5-oxocyclopent-1-enyl)isobenzofuran-1(3H)-one (4) 和 2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1H-indene-1,研究了 3(2H)-二酮 (5)。我们注意到，对于化合物 1 到 4，在固体、溶液或气相中仅观察到烯醇形式。它们的互变异构平衡不受溶剂、温度或物理条件的影响。状态。在溶液

  DOI：

  10.1016/j.molstruc.2016.02.015

文献信息

• Regiospecific synthesis of 3-(2,6-dihydroxyphenyl)phthalides: application to the synthesis of isopestacin and cryphonectric acid
  作者：Dipakranjan Mal、Pallab Pahari、Saroj Ranjan De

  DOI：10.1016/j.tet.2007.08.048

  日期：2007.11

  DBU catalyzed condensation of phthalaldehydic acids and 1,3-diketones has been developed to be a general method for the synthesis of 3-substituted phthalides. This method, in combination with mercuric acetate mediated oxidative aromatization has been utilized for the regiospecific synthesis of isopestacin (9) and cryphonectric acid (10).

  已经开发出DBU催化的邻苯二甲酸和1，3-二酮的缩合反应，是合成3-取代的邻苯二甲酸酯的通用方法。该方法与乙酸汞介导的氧化芳构化相结合，已被用于异雌霉素（9）和冷柠檬酸（10）的区域特异性合成。
• Association of electroanalytical and spectrophotometric methods to evaluate the antioxidant activity of isobenzofuranone in primary cultures of hippocampal neurons
  作者：Aniely dos Reis Teixeira、Róbson Ricardo Teixeira、Iara Mariana Lellis Ribeiro、Wagner Luiz Pereira、Taise Matte Manhabosco、Ana Carolina Ferreira de Brito、Laser Antônio Machado Oliveira、Katiane de Oliveira Pinto Coelho Nogueira

  DOI：10.1016/j.tiv.2020.104970

  日期：2020.10

  The isobenzofuran-1(3H)-ones (phthalides) exhibit various biological activities, including antioxidant activity on reactive oxygen species (ROS). An excess of ROS that cannot be naturally contained by cellular enzymatic systems is called redox imbalance, which damage cell membranes, proteins, and DNA, thereby possibly triggering neuronal death in several neurodegenerative diseases. Considering our ongoing efforts to find useful compounds to control redox imbalance, herein we evaluated the antioxidant activity of two phtalides (compounds 3 and 4), using primary cultures of hippocampal neurons. Spectrophotometric assays showed that compound 3 significantly reduced (p <= 0.05) ROS levels and lipid peroxidation compared to the control treatment, while compound 4 was unable at any of the tested concentrations. Despite their structural similarity, these compounds behave differently in the intracellular environment, which was reliably corroborated by the determination of oxidation potentials via cyclic voltammetry. It was demonstrated that compound 3 presents a lower oxidation potential. The combination of the mentioned methods allowed us to find a strong correlation between the chemical structure of compounds and their biological effects. Taking together, the results indicate that compound 3 presents desirable characteristics to act as a candidate pharmacological agent for use in the prevention and treatment of neurodegenerative diseases.
• 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.