2-(1,3-dihydro-3-oxo-1-isobenzofuranyl)-1H-indene-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(1,3-dihydro-3-oxo-1-isobenzofuranyl)-1H-indene-1,3(2H)-dione
• 英文别名: 2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1H-indene-1,3(2H)-dione；2-(3-Oxo-1,3-dihydroisobenzofuran-1-yl)-1h-indene-1,3(2h)-dione；2-(3-oxo-1H-2-benzofuran-1-yl)indene-1,3-dione
• 化学式: C₁₇H₁₀O₄
• 分子量: 278.264
• InChiKey: HQKHRBFUPKLLSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 邻羧基苯甲醛 在 sulfuric acid immobilized on silica 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以76%的产率得到2-(1,3-dihydro-3-oxo-1-isobenzofuranyl)-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  无溶剂条件下在硅胶上固溶有硫磺酸的一锅法合成异苯并呋喃-1（3H）的方法及三阶非线性光学性质的研究

  摘要：

  摘要已经描述了通过使用固定在二氧化硅（H 2 SO 4 -SiO 2）上的硫酸使邻苯二甲酸（2-羧基苯甲醛）与甲基芳基或环酮反应，可无溶剂合成异苯并呋喃-1（3 H）-收率（70–88％）。催化剂可以通过简单的过滤回收并重复使用。而且，其中一些化合物已经通过激光高斯z扫描技术研究了三阶非线性光学性质。电子邮件：[e-mail]简介异苯并呋喃-1（3 H）-及其衍生物是非常重要的生物化合物，广泛存在于天然产物中。典型的例子是fuscinarin（1）1，邻苯二甲酰胺（2）2，catalpalactone（3）3，alcyopterosin E（4）4，（+）-spirolaxine（5）5，vermistatin（6）6，rubiginone-H（7） ）7，（-）-胱氨酸（8）8，异司他汀（9）9和冷冻柠檬酸（10）10。图1.该家族的一些成员表现出有趣的生理活性，并在

  DOI：

  10.4067/s0717-97072015000100011

文献信息

• Nuclear Magnetic Resonance (NMR), Infrared (IR) and Mass Spectrometry (MS) study of keto-enol tautomerism of isobenzofuran-1(3H)-one derivatives
  作者：Diego Arantes Teixeira Pires、Wagner Luiz Pereira、Róbson Ricardo Teixeira、José Daniel Figueroa-Villar、Claudia Jorge do Nascimento

  DOI：10.1016/j.molstruc.2016.02.015

  日期：2016.6

  Abstract The keto-enol tautomerism of 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) and 2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-1H-indene-1,3(2H)-dione (5) were investigated

  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
• Regiospecific synthesis of isopestacin, a naturally occurring isobenzofuranone antioxidant
  作者：Pallab Pahari、Bidyut Senapati、Dipakranjan Mal

  DOI：10.1016/j.tetlet.2004.04.175

  日期：2004.6

  A DBU promoted aldol cyclocondensation of hydroxyisobenzofuranone 15 with cyclohexane-1,3-dione, followed by aromatization has resulted in the first short synthesis of isopestacin (1).

  DBU促进了羟基异苯并呋喃酮15与环己烷1,3-二酮的羟醛缩合反应，然后进行芳构化，首次合成了异黄霉素（1）。
• 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。
• Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones
  作者：Róbson Teixeira、Gustavo Bressan、Wagner Pereira、Joana Ferreira、Fabrício de Oliveira、Deborah Thomaz

  DOI：10.3390/molecules18021881

  日期：——

  A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.

  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。
• The Antileishmanial Potential of C-3 Functionalized Isobenzofuranones against Leishmania (Leishmania) Infantum Chagasi
  作者：Wagner Pereira、Raphael de Souza Vasconcellos、Christiane Mariotini-Moura、Rodrigo Saar Gomes、Rafaela Firmino、Adalberto da Silva、Abelardo Silva Júnior、Gustavo Bressan、Márcia Almeida、Luís Crocco Afonso、Róbson Teixeira、Juliana Lopes Rangel Fietto

  DOI：10.3390/molecules201219857

  日期：——

  Leishmaniases are diseases caused by protozoan parasites of the genus Leishmania. Clinically, leishmaniases range from cutaneous to visceral forms, with estimated global incidences of 1.2 and 0.4 million cases per year, respectively. The treatment of these diseases relies on multiple parenteral injections with pentavalent antimonials or amphotericin B. However, these pharmaceuticals are either too toxic or expensive for routine use in developing countries. These facts call for safer, cheaper, and more effective new antileishmanial drugs. In this investigation, we describe the results of the assessment of the activities of a series of isobenzofuran-1(3H)-ones (phtalides) against Leishmania (Leishmania) infantum chagasi, which is the main causative agent of visceral leishmaniasis in the New World. The compounds were tested at concentrations of 100, 75, 50, 25 and 6.25 µM over 24, 48, and 72 h. After 48 h of treatment at the 100 µM concentration, compounds 7 and 8 decreased parasite viability to 4% and 6%, respectively. The concentration that gives half-maximal responses (LC50) for the antileishmanial activities of compounds 7 and 8 against promastigotes after 24 h were 60.48 and 65.93 µM, respectively. Additionally, compounds 7 and 8 significantly reduced parasite infection in macrophages.

  利什曼病是由利什曼属的原生动物寄生虫引起的疾病。临床上，利什曼病从皮肤型到内脏型不等，全球估计每年分别有120万和40万例病例。这些疾病的治疗依赖于多次静脉注射五价锑或两性霉素B。然而，这些药物要么毒性过大，要么价格昂贵，不适宜在发展中国家常规使用。这些事实呼吁更安全、更廉价、更有效的新型抗利什曼药物。在本研究中，我们描述了评估一系列异苯并呋喃-1(3H)-酮（酞类）对利什曼原虫（Leishmania）婴儿型查加斯菌活性结果，该菌是新大陆内脏利什曼病的主要致病因子。这些化合物在100、75、50、25和6.25微摩尔浓度下分别测试了24、48和72小时。经过100微摩尔浓度下48小时的治疗后，化合物7和8分别将寄生虫存活率降低到4%和6%。在24小时后，化合物7和8对前鞭毛体的半最大效应浓度（LC50）分别是60.48和65.93微摩尔。此外，化合物7和8显著减少了巨噬细胞中的寄生虫感染。