6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione | 82218-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione
• 英文别名: 6,8-dimethoxy-4H-isochromene-1,3-dione；3,5-dimethoxyhomophthalic anhydride；6,8-dimethoxyhomophthalic anhydride；6,8-dimethoxy-isochroman-1,3-dione；3,5-Dimethoxyphthalsaeureanhydrid；6,8-Dimethoxyisochroman-1,3-dione
• CAS: 82218-06-2
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: UCQGXKTVLKNSOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione 在 aluminum (III) chloride 、 氧气 、 sodium hydride 、 sodium chloride 作用下， 以 四氢呋喃 、 邻二氯苯 、 mineral oil 为溶剂， 反应 3.03h， 生成 variecolortide B
  参考文献：
  名称：

  通过异常的杂Diels-Alder反应简捷地合成各种色素A和B

  摘要：

  某些蒽醌和二酮哌嗪的融合体是对variecolortides（一种不寻常的真菌生物碱家族）的恰当描述。在新的，简洁的变色色素A和B的总合成中，天然外消旋物的聚合程度很高，几乎没有保护基团的操纵。螺环核心是由1,4-蒽醌与二氢二酮哌嗪的异Diels-Alder反应生成的。

  DOI：

  10.1002/anie.201006154
• 作为产物：
  描述：

  5,7-二甲氧基茚酮 在 双氧水 、 sodium methylate 、 乙酸酐 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione
  参考文献：
  名称：

  Discovery of 2-aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-ones as novel EGFR inhibitor by scaffold hopping

  摘要：

  2-Aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-one has been proposed as a novel scaffold of EGFR inhibitor based on scaffold hoping. In the present study, a series of 2-aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-one derivatives were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against two human cancer cell lines, including A431 and A549. The SAR of the title compounds was preliminarily discussed. The compounds with ideal inhibition were evaluated through ELISA-based EGFR-TK assay. Compound 6c showed the best activity against A431 and EGFR tyrosine kinase. These findings suggest that title compounds are EGFR inhibitors with novel structures. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.027
• 作为试剂：
  描述：

  2-carboxymethyl-4,6-dimethoxy-benzoic acid 、 乙酸酐 在 6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione 、 甲苯 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以6,8-Dimethoxyisochroman-1,3-dione (25) (3.05g) was isolated as a yellow crystalline solid的产率得到6,8-dimethoxy-1H-2-benzopyran-1,3(4H)-dione
  参考文献：
  名称：

  Process for preparing isocoumarins

  摘要：

  本发明提供一种制备异香豆素-3-基衍生物的过程，包括在反应介质中，在酸催化剂存在下，将同间苯二酐衍生物与含有酰基活化基团的羰基化合物反应。该反应介质包括溶剂和碱。本发明还包括一种制备同间苯酸酐反应物所用的同间苯酸酯的过程，以及一种综合过程，其中这两个反应依次进行，以得到所需的异香豆素衍生物。

  公开号：

  US06664401B2

文献信息

• COMPOUNDS FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES
  申请人：Wong Norman C.W.

  公开号：US20080188467A1

  公开（公告）日：2008-08-07

  The present disclosure relates to compounds, which are useful for regulating the expression of apolipoprotein A-I (ApoA-I), and their use for treatment and prevention of cardiovascular disease and related disease states, including cholesterol- or lipid-related disorders, such as, for example, atherosclerosis.

  本公开涉及化合物，这些化合物可用于调节载脂蛋白A-I（ApoA-I）的表达，以及它们用于治疗和预防心血管疾病及相关疾病状态，包括胆固醇或脂质相关紊乱，例如，动脉粥样硬化。
• TREATMENT OF DISEASES BY EPIGENETIC REGULATION
  申请人：McLure Kevin G.

  公开号：US20130281397A1

  公开（公告）日：2013-10-24

  The present disclosure provides non-naturally occurring polyphenol compounds that inhibit the bromodomain and extra terminal domain (BET) proteins. The disclosed compositions and methods can be used for treatment and prevention of cancer, including NUT midline carcinoma, Burkitt's Lymphoma, Acute Myelogenous Leukemia, and Multiple Myeloma; autoimmune or inflammatory diseases or conditions, and sepsis.

  本公开提供了抑制溴结构域和额外末端结构域（BET）蛋白的非天然存在的多酚化合物。所公开的组合物和方法可用于治疗和预防癌症，包括NUT中线癌、Burkitt淋巴瘤、急性髓系白血病和多发性骨髓瘤；自身免疫或炎症性疾病或症状，以及败血症。
• Synthetic studies on nogalamycin congeners [4]1,2 syntheses amd antitumor activity of various nogalamycin congeners
  作者：Fuyuhiko Matsuda、Motoji Kawasaki、Masako Ohsaki、Kaoru Yamada、Shiro Terashima

  DOI：10.1016/s0040-4020(01)81434-4

  日期：1988.1

  Various structural types of nogalamycin congeners and their partial structures, which had been previously synthesized in the course of our synthetic studies on the total syntheses or were originally produced by employing the explored synthetic scheme, were subjected to in vitro cytotoxicity and in vivo antitumor activity assay against P388 munne leukemia. These studies obviously disclosed novel aspects

  在我们的合成研究总过程中先前合成的或最初通过探索的合成方案生产的诺加霉素同系物的各种结构类型及其部分结构，均经过了体外细胞毒性和体内抗肿瘤活性的测定抵抗P388 munne白血病。这些研究显然揭示了诺加霉素同类物的结构-活性关系的新颖方面。
• Synthesis of Homophthalates from Allenic Diesters: Conversion into Viocristin and Analogues, and Application to 6-Methylpretetramid.
  作者：Donald W. Cameron、Ece Caliskan、Peter G. Griffiths

  DOI：10.1071/ch99065

  日期：——

  Oxy-substituted homophthalic anhydrides have been synthesized by cycloaddition of di- and tri-oxy butadienes to the allenic diester (1). By base-catalysed cycloaddition to appropriate benzoquinones they have afforded new syntheses of viocristin (19), isoviocristin (20) and analogous 1,4-anthraquinones. Related chemistry has led to the naphthalene (34) and the anhydride (35), intermediates in published syntheses of semivioxanthin and 6- methylpretetramid respectively.

  氧代均苯二甲酸酐是通过二氧和三氧丁二烯与异链二酯（1）的环加成反应合成的。 将二氧基和三氧基丁二烯环加成均苯二甲酸酯 (1)。通过碱催化 通过与适当的苯醌进行环加成，他们合成了新的 viocristin (19)、isoviocristin (20) 和类似的 1,4-anthraquinones 的新合成。相关的 萘（34）和酐（35）、 的中间体。 萘 (34) 和酸酐 (35)，它们分别是已发表的半二氧杂蒽和 6-甲基维甲酸合成的中间体。
• Total Synthesis and Structural Revision of Viridicatumtoxin B
  作者：K. C. Nicolaou、Christian Nilewski、Christopher R. H. Hale、Heraklidia A. Ioannidou、Abdelatif ElMarrouni、Lizanne G. Koch

  DOI：10.1002/anie.201304691

  日期：2013.8.12

  Will the real viridicatumtoxin B please stand up: The total synthesis of viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline‐like antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule.

  请真正的绿藻毒素 B 站起来：绿藻毒素 B的全合成导致其结构修正，并为这种复杂的四环素类抗生素的类似物构建和生物学评价开辟了道路。采用的高度收敛策略允许快速构建分子的整个碳环框架。