4-hydroxy-2H,5H-pyrano[3,2-c]benzo[1]pyran-2,5-dione | 16052-81-6

• 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-2H,5H-pyrano[3,2-c]benzo[1]pyran-2,5-dione
• 英文别名: 4-hydroxy-2H,5H-pyrano[3,2-c]chromen-2,5-dione；4'-Hydroxy-1.2-pyrono-5.6':3.4-cumarin；4'-Hydroxy-<1,2-pyrono-5',6':3,4-cumarin>；4-Hydroxy-2H,5H-pyrano<3,2-c>benzopyran-2,5-dion；4-Hydroxy-2.5-dioxo-(2H.5H-pyrano<3,2-c><1>benzopyran)；4-hydroxy-pyrano[3,2-c]chromene-2,5-dione；4-Hydroxy-2H,5H-pyrano[3,2-c][1]benzopyran-2,5-dione；4-hydroxypyrano[3,2-c]chromene-2,5-dione
• CAS: 16052-81-6
• 化学式: C₁₂H₆O₅
• 分子量: 230.177
• InChiKey: SEUYEPDUKPAJOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2H,5H-pyrano[3,2-c]benzo[1]pyran-2,5-dione 在 乙酸酐 作用下， 生成 4-acetoxy-pyrano[3,2-c]chromene-2,5-dione
  参考文献：
  名称：

  Zur Chemie des 4-Hydroxy-cumarins

  摘要：

  DOI：

  10.1007/bf00902633
• 作为产物：
  描述：

  苯酚 在 zinc(II) chloride 、 三氯氧磷 作用下， 生成 4-hydroxy-2H,5H-pyrano[3,2-c]benzo[1]pyran-2,5-dione
  参考文献：
  名称：

  Chromenone derivatives as a versatile scaffold with dual mode of inhibition of HIV-1 reverse transcriptase-associated Ribonuclease H function and integrase activity

  摘要：

  A number of compounds targeting different processes of the Human Immunodeficiency Virus type 1 (HIV-1) life cycle have been developed in the continuing fight against AIDS. Coumarin-based molecules already proved to act as HIV-1 Protease (PR) or Integrase (IN) inhibitors and also to target HIV-1 reverse transcriptase (RT), blocking the DNA-dependent DNA-polymerase activity or the RNA-dependent DNA-polymerase activity working as common NNRTIs. In the present study, with the aim to exploit a coumarin-based scaffold to achieve the inhibition of multiple viral coded enzymatic functions, novel 4-hydroxy-2H, 5H-pyrano (3, 2-c) chromene-2, 5 dione derivatives were synthesized. The modeling studies calculated the theoretical binding affinity of the synthesized compounds on both HIV-1 IN and RT-associated Ribonuclease H (RNase H) active sites, which was confirmed by biological assays. Our results provide a basis for the identification of dual HIV-1 IN and RT RNase H inhibitors compounds. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111617

文献信息

• Reactions with 2(1<i>H</i>)-Quinolinone and Coumarine Derivatives: New Routes to Polysubstituted 2(1<i>H</i>)-Quinolinone and Coumarine Derivatives
  作者：Fathy Mohamed Abdel Aziz El-Taweel、Salah Zaki Ahmed Sowellim、Abdel Ghani Ali Elagamey

  DOI：10.1246/bcsj.68.905

  日期：1995.3

  Whereas 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione (2a) or 3-acetyl-1-methyl-2(1H)-quinolinone (3a) reacted with the benzylidenenitriles 1a—f or a mixture of either malononitrile or ethyl cyanoacetate and aromatic aldehydes in ethanol/piperidine to give 4H-pyran derivatives 8, the reaction of 2b,c or 3b,c with the same reagents afforded 4,6-dihydro-5H-pyrano[3,2-c]quinolin-5-ones 11. Compounds 11 were

  而2H-吡喃并[3,2-c]喹啉-2,5(6H)-二酮(2a)或3-乙酰基-1-甲基-2(1H)-喹啉酮(3a)与亚苄基腈1a-f或丙二腈或氰基乙酸乙酯和芳香醛在乙醇/哌啶中的混合物得到 4H-吡喃衍生物 8，2b,c 或 3b,c 与相同的试剂反应得到 4,6-二氢-5H-吡喃 [3, 2-c]quinolin-5-ones 11. 化合物 11 也由 1a-f 和 3d,e,f 制备。吡喃并[3,2-c]香豆素2d与1a反应生成6H,11H-[2]苯并吡喃[4,3-c][1]苯并吡喃-6,11-二酮(15)。用氰化钾水溶液或羟胺处理 17 分别得到 2(1H)-喹啉酮衍生物 19 和 20。
• Efficient syntheses and antimicrobial activities of new thiophene containing pyranone and quinolinone derivatives using manganese(<scp>iii</scp>) acetate: the effect of thiophene on ring closure–opening reactions
  作者：Mehtap Özgür、Mehmet Yılmaz、Hiroshi Nishino、Eda Çinar Avar、Hakan Dal、A. Tarık Pekel、Tuncer Hökelek

  DOI：10.1039/c9nj00054b

  日期：——

  The syntheses of a new series of pyranones, namely, fused pyranones and quinoline-based dihydrofurans, accompanied by 3-alkenyl-substituted structures were investigated. The products were regioselectively formed by Mn(III)-mediated oxidation at elevated temperature in excellent yields. The effects of the thiophene group and reaction temperature and time on product distributions were investigated. The

  研究了一系列新的吡喃酮，即稠合的吡喃酮和喹啉基二氢呋喃，并伴有3-烯基取代的结构。该产物通过Mn（III）介导的氧化在高温下区域选择性地形成，具有优异的产率。研究了噻吩基团，反应温度和时间对产物分布的影响。合成的化合物的结构根据光谱学（IR，1 H NMR，13 C NMR，COSY，HSQC，HMBC和元素分析）和X射线晶体学数据确定。另外，体外使用圆盘扩散法测试了一些合成的二氢呋喃对G（+）和G（-）细菌的抗菌活性。结果表明，含有噻吩基团的化合物显示出比某些常用抗生素更好的抗菌作用。
• Matsui; Ota, Nippon Kagaku Zasshi, 1957, vol. 78, p. 517,518
  作者：Matsui、Ota

  DOI：——

  日期：——
• Eine breit anwendbare Synthese fluoreszierender kondensierter ?-Pyrone
  作者：Otto S. Wolfbeis、Erich Ziegler、Andreas Knierzinger、Helmut Wipfler、Iris Trummer

  DOI：10.1007/bf00938720

  日期：——
• Nakata, Nippon Kagaku Zasshi, 1957, vol. 78, p. 1780,1783
  作者：Nakata

  DOI：——

  日期：——