4-hydroxy-5-methoxy coumarin | 53666-76-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-hydroxy-5-methoxy coumarin
• 英文别名: 5-methoxy-4-hydroxycoumarin；4-Hydroxy-5-methoxy-2H-1-benzopyran-2-one；4-hydroxy-5-methoxychromen-2-one
• CAS: 53666-76-5
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: LFFCJEOKCYTBDD-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C(Solv: ethanol (64-17-5))
• 沸点：
  403.1±45.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-methoxy coumarin 在 四(三苯基膦)钯 四氯化碳 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醇 、 苯 为溶剂， 反应 26.0h， 生成 5-methoxy-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins

  摘要：

  在铃木反应条件下，钯催化 4-氯或 4-溴香豆素 1-4 与芳基硼酸 5-13 的偶联反应是获得 4-芳基香豆素的有效途径。在改良的铃木反应条件下，使用碘化铜（I）作为辅助催化剂，将 4-三氟甲基-磺酰氧基香豆素 35-38 与芳基硼酸进行处理，也能以良好的收率（70-97%）获得这些 4-芳基香豆素。

  DOI：

  10.1039/p19960002591
• 作为产物：
  描述：

  N,N-Diethyl-3-(2-hydroxy-6-methoxy-phenyl)-3-oxo-propionamide 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以89%的产率得到4-hydroxy-5-methoxy coumarin
  参考文献：
  名称：

  Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

  摘要：

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00977-0

文献信息

• Novel water-soluble anticancer agents derived from 4-arylcoumarins
  作者：Yu. B. Malysheva、Yu. V. Voitovich、E. A. Sharonova、S. Combes、E. V. Svirshchevskaya、E. L. Vodovozova、A. Yu. Fedorov

  DOI：10.1007/s11172-013-0149-3

  日期：2013.4

  Novel 4-arylcoumarin derivatives were obtained. They are water-soluble analogs of the well-known anticancer drug combretastatin A-4. The key step of the synthesis involves the Suzuki-Miyaura cross-coupling. The water-soluble salts obtained exhibit considerable cytotoxic activity against the HBL-100 and HaCaT cell lines.

  获得了新的 4-芳基香豆素衍生物。它们是众所周知的抗癌药物考布他汀 A-4 的水溶性类似物。合成的关键步骤涉及 Suzuki-Miyaura 交叉偶联。获得的水溶性盐对 HBL-100 和 HaCaT 细胞系表现出相当大的细胞毒活性。
• Selective Benzopyranone and Pyrimido[2,1-<i>a</i>]isoquinolin-4-one Inhibitors of DNA-Dependent Protein Kinase:  Synthesis, Structure−Activity Studies, and Radiosensitization of a Human Tumor Cell Line in Vitro
  作者：Roger J. Griffin、Gabriele Fontana、Bernard T. Golding、Sophie Guiard、Ian R. Hardcastle、Justin J. J. Leahy、Niall Martin、Caroline Richardson、Laurent Rigoreau、Martin Stockley、Graeme C. M. Smith

  DOI：10.1021/jm049526a

  日期：2005.1.1

  scaffolds were less potent. Crucially, these studies revealed a very constrained structure-activity relationship at the 2-position of the benzopyranone and pyrimido[2,1-a]isoquinolin-4-one pharmacophore, with only a 2-morpholino or 2-(2'-methylmorpholino) group being tolerated at this position. More detailed biological studies conducted with the most potent inhibitor NU7163 (48; IC(50) = 0.19 microM) demonstrated

  合成了各种各样的chromen-2-one，chromen-4-one和pyrimidoisoquinolin-4-one衍生物，并评估了其对DNA修复酶DNA依赖性蛋白激酶（DNA-PK）的抑制活性，目的是阐明效价和激酶选择性的构效关系。DNA-PK抑制活性在评估的一系列化合物（IC（50）值范围从0.19到> 10 microM）上有很大差异，其中7,8-苯并铬基-4-酮和嘧啶基[2,1]表现出优异的活性。 -a] isoquinolin-4-one模板。相比之下，基于苯并色素-2-酮（香豆素）或2-芳基-7,8-苯并色素-4-酮（黄酮）支架的抑制剂效力较低。至关重要的是，这些研究揭示了在苯并吡喃酮和嘧啶基2位上的结构活性关系非常受约束[2，1-a]异喹啉-4-酮药效基团，在此位置仅可耐受2-吗啉代或2-（2'-甲基吗啉代）基团。用最有效的抑制剂NU7163（48; IC（50）= 0
• Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2-<i>c</i>]coumarin Derivatives and Evaluation for Photophysical Properties
  作者：Xi Feng、Zhen Qin、Xinying Cheng、Dongyu Liu、Yinghe Peng、Huidan Huang、Bin Song、Jinlei Bian、Zhiyu Li

  DOI：10.1021/acs.joc.1c00835

  日期：2021.9.17

  An efficient protocol for synthesizing furo[3,2-c]coumarin derivatives is described. The novel reaction could afford the desired furocoumarins with good to excellent yields in a mild and rapid manner. Large substrate scope screening and scale-up preparation have also been accomplished, and selected compounds were evaluated for their photophysical properties.

  描述了合成呋喃 [3,2- c ] 香豆素衍生物的有效方案。该新反应可以以温和快速的方式提供所需的呋喃香豆素，收率良好至极好。还完成了大型底物范围筛选和放大制备，并对选定的化合物的光物理特性进行了评估。
• Therapeutic agents
  申请人：The Boots Company PLC

  公开号：EP0354693A1

  公开（公告）日：1990-02-14

  This invention relates to compounds of formula I wherein R₁ represents hydrogen or together with R₂ represents a bond; R₂ together with either one of R₁ and R₃ represents a bond; R₃ together with either one of R₂ and R₄ represents a bond; R₄ represents hydrogen or together with R₃ represents a bond; R₅ represents hydrogen or methyl; R₆ represents hydrogen, halo, a C₂₋₆ alkanoyl group, a C₂₋₆ alkoxycarbonyl group, a C₁₋₆ alkylthio group, a C₁₋₆ alkylsulphinyl group, a C₁₋₆ alkylsulphonyl group, carbamoyl, carboxy, or R₅ and R₆ together with the carbon atom to which they are attached represent a cyclopropyl group; R₇ represents hydrogen, halo, trifluoromethyl, methoxy, a C₁₋₆ alkyl group, a C₁₋₆ alkylthio group or a C₁₋₆ alkylsulphinyl group; R₈ represents hydrogen, halo or trifluoromethyl; R₉ and R₁₀, which may be the same or different, each represent halo; or R₉ represents hydrogen and R₁₀ represents hydrogen, halo, trifluoromethyl, hydroxy, nitro, a C₂₋₆ alkanoyloxy group, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group, which have immunomodulatory activity. Compositions containing these compounds and processes to make them are also disclosed.

  这项发明涉及具有以下结构的化合物，其中R₁代表氢或与R₂一起代表键；R₂与R₁或R₃中的任一者一起代表键；R₃与R₂或R₄中的任一者一起代表键；R₄代表氢或与R₃一起代表键；R₅代表氢或甲基；R₆代表氢、卤素、C₂₋₆烷酰基、C₂₋₆烷氧羰基、C₁₋₆烷基硫基、C₁₋₆烷基砜基、C₁₋₆烷基砜基、氨基甲酰基、羧基，或R₅和R₆与它们连接的碳原子一起代表环丙基；R₇代表氢、卤素、三氟甲基、甲氧基、C₁₋₆烷基、C₁₋₆烷基硫基或C₁₋₆烷基砜基；R₈代表氢、卤素或三氟甲基；R₉和R₁₀，可以相同也可以不同，每个代表卤素；或R₉代表氢，R₁₀代表氢、卤素、三氟甲基、羟基、硝基、C₂₋₆烷酰氧基、C₁₋₆烷基或C₁₋₆烷氧基，具有免疫调节活性。还公开了含有这些化合物的组合物和制备它们的方法。
• [EN] SUBSTITUTED FUROCHROMENE COMPOUNDS OF ANTIINFLAMMATORY ACTION<br/>[FR] COMPOSES DE FUROCHROMENE SUBSTITUES A ACTION ANTI-INFLAMMATOIRE
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005010006A1

  公开（公告）日：2005-02-03

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diseases and/or conditions in humans.

  本发明涉及公式（I）的新化合物，包括所有立体异构体和互变异构体，以及其药用可接受盐和溶剂合物，用于预防和治疗人类的哮喘和其他炎症性疾病和/或情况的过程和反应中间体，以及它们的使用。