7-羟基-4-氧代-4H-1-苯并吡喃-3-羧醛 | 42059-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 7-羟基-4-氧代-4H-1-苯并吡喃-3-羧醛
• 英文名称: 7-hydroxy-3-formylchromone
• 英文别名: 7-hydroxy-4-oxo-4H-chromene-3-carbaldehyde；7-hydroxy-3-formyl-4H-chromen-4-one；3-Formyl-7-hydroxychromone；7-hydroxy-4-oxochromene-3-carbaldehyde
• CAS: 42059-55-2
• 化学式: C₁₀H₆O₄
• 分子量: 190.155
• InChiKey: ZTPHGPLCHXGENO-UHFFFAOYSA-N

物化性质

• 熔点：
  265-270 °C
• 沸点：
  406.8±45.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  7-羟基-4-氧代-4H-1-苯并吡喃-3-羧醛 在 哌啶 、 zinc diacetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-[5-(3-nitrophenyl)-2-phenylpyrazol-3-yl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
  参考文献：
  名称：

  Computational evaluation and experimental verification of antibacterial and antioxidant activity of 7-hydroxy-3-pyrazolyl-4H-chromen-4-ones and their o-glucosides: identification of pharmacophore sites

  摘要：

  This paper reports the computational evaluation and experimental verification of 7-hydroxy-3-(1-phenyl-3-aryl-1H-pyrazol-5-yl)-4H-chromen-4-ones 3 and their o-beta-d-glucopyranosides 5 for their antimicrobial and antioxidant activity. The prepared compounds were tested against various Gram-positive and Gram-negative bacteria species. Some of the synthesized compounds have shown potential antimicrobial and antioxidant activity. This POM bioinformatic study could greatly help to pharmacomodulate the potential antibiotics and antioxidants.This paper describes the computational POM (Petra/Osiris/Molinspiration) evaluation and experimental verification of 7-o-beta-d-glucopyranosyloxy-3-(1-phenyl-3-aryl-1H-pyrazol-5-yl)-4H-chromen-4-ones and metabolites for their antimicrobial and antioxidant activity.

  DOI：

  10.1007/s00044-013-0621-5
• 作为产物：
  描述：

  丹皮酚 在 三氟化硼乙醚 、 乙酸酐 、 三溴化硼 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 7-羟基-4-氧代-4H-1-苯并吡喃-3-羧醛
  参考文献：
  名称：

  Synthesis and DNA Binding Affinity of Some New 7-Hydroxy-3-Carbaldehyde Chromones

  摘要：

  Two novel ligands, 7-methoxy chromone-3-carbaldehyde-salicylyl hydrazone and 7-hydroxy chromone-3-carbaldehyde-salicylyl hydrazone, were prepared by resorcinol. Their respective Eu (III) complexes had been synthesized and characterized on the base of elemental analyses, molar conductivities, IR spectra, mass spectra, UV-Vis spectra, and fluorescence studies. The interactions of the Eu (III) complexes and their ligands with calf-thymus DNA were investigated, which were found that both two ligands and their rare earth complexes could strongly bind with calf-thymus DNA via an intercalation mechanism.

  DOI：

  10.1080/15533174.2013.831451

文献信息

• Novel p-Functionalized Chromen-4-on-3-yl Chalcones Bearing Astonishing Boronic Acid Moiety as MDM2 Inhibitor: Synthesis, Cytotoxic Evaluation and Simulation Studies
  作者：Richa K. Bhatia、Lakhwinder Singh、Ruchika Garg、Maninder Kaur、Manmohan Yadav、Jitender Madan、Satyavathi Kancherla、Raghuvir R.S. Pissurlenkar、Evans C. Coutinho

  DOI：10.2174/1573406415666190531123751

  日期：2020.2.20

  Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenylboronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substitutedphenyl) prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines.

  The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 protein.

  Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322).

  Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 µM) overall against tested cancer cell lines. Interestingly, para- Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 µM. Besides the emblematic hydrophobic interactions of MDM2 inhibitors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells.

  Novel compounds were obtained with good anticancer activity especially 6- Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

  背景： 新型4-[3-(6/7/8-取代的4-氧代-4H-香豆素-3-基)丙烯酰基]苯硼酸衍生物（5a-h）以及其他6/7/8-取代的3-(3-氧代-3-(4-取代苯基)丙-1-烯基)-4H-香豆素-4-酮衍生物（3a-u）被设计为p53-MDM2通路抑制剂，并据报道对多种癌细胞系具有显著的细胞毒性特性。 目的： 当前项目旨在构建香豆素-4-酮-3-基查尔酮（3a-u/5a-h）的结构-抗癌活性关系。此外，对这些香豆素-查尔酮进行了对接研究，以深入了解它们与MDM2蛋白的相互作用可能性。 方法： 利用硅胶支持的HClO4（绿色路线，收率极高）制备了29种香豆素-4-酮-3-基查尔酮衍生物（3a-u/5a-h），并对四种癌细胞系（HCT116、MCF-7、THP-1、NCIH322）进行了测试。 结果： 在系列3a-u中，化合物3b表现出最高的抗癌活性（IC50值在8.6至28.4 µM范围内）对所有测试的癌细胞系都具有活性。有趣的是，对位硼酸衍生物（5b）显示出对结肠癌细胞系HCT-116的选择性抑制作用，IC50值为2.35 µM。除了MDM2抑制剂的标志性疏水相互作用外，衍生物5b在分子动力学（MD）模拟中发现与MDM2的GLN59和GLN72残基有额外的氢键作用。所有化合物对正常成纤维细胞几乎无毒。 结论： 获得了具有良好抗癌活性的新化合物，尤其是6-氯香豆素-4-酮取代硼酸衍生物5b。分子对接研究表明，作为MDM-2抑制剂，它具有良好的活性，暗示与MDM2的疏水相互作用以及氢键作用。
• Convenient Synthesis of Fluorescent Chromeno[4,3-d]pyrimidines from Electron-Deficient 3-Vinylchromones
  作者：Nikita M. Chernov、Roman V. Shutov、Anastasia E. Potapova、Igor P. Yakovlev

  DOI：10.1055/s-0039-1690723

  日期：2020.1

  We report an easy and powerful approach to the synthesis of novel chromeno[4,3-d]pyrimidine-5-acetic acids through ANRORC reaction of electron-deficient 3-vinylchromones and 1,3-N,N-binucleophiles. The reaction proceeds under mild conditions (EtOH, rt) and is applicable to a wide range of substrates. The described compounds show fluorescence in the violet-blue range (390–460 nm) with Stokes shift of

  我们报告了一种简单而强大的方法，通过缺电子的3-乙烯基色酮和1,3- N，N-双亲核试剂的ANRORC反应合成新型铬诺[4,3 - d ]嘧啶-5-乙酸。反应在温和的条件下（EtOH，rt）进行，适用于多种底物。所描述的化合物在紫蓝色范围（390–460 nm）中显示荧光，斯托克斯位移为40–80 nm，量子产率适中（0.15–0.20）。由于吸电子基团以乙酸片段的形式保守，因此这些化合物可以容易地被官能化或缀合至所需的底物以用于（生物）分析目的。
• Design, synthesis and anti-TMV activities of novel chromone derivatives containing dithioacetal moiety
  作者：Miao Li、Ningning Zan、Maoxi Huang、Donghao Jiang、Deyu Hu、Baoan Song

  DOI：10.1016/j.bmcl.2019.126945

  日期：2020.3

  Thirty-five novel chromone derivatives containing dithioacetal moiety were designed, synthesized, and their anti-TMV activities were evaluated through half-leaf method. The results showed compound c23 illustrates highly curative, protective and inactivating activities against TMV at 500 mg/L, with the values of 68.8%, 58.8%, 86.0% respectively, which were superior to that of Ribavirin (42.3%, 49.8%

  设计合成了二十五种含二硫缩醛部分的色酮衍生物，并通过半叶法评价了它们的抗TMV活性。结果表明，化合物c23对500 mg / L的TMV具有很高的治愈，保护和灭活活性，其值分别为68.8％，58.8％，86.0％，优于利巴韦林（42.3％，49.8％，68.4）分别为％和宁南霉素（分别为59.4％，52.4％，88.4％）。化合物c23的灭活活性EC50值为9.3 mg / L，优于利巴韦林（135.2 mg / L），与宁南霉素（8.8 mg / L）相当。此外，化合物c23可以破坏TMV-CP的完整性，导致TMV的传染性降低。同时，化合物c23可与TMV蛋白涂层结合并水解TMV蛋白涂层，影响TMV的自组装过程，缔合常数（Kd）为4.5 mg / L。这一发现表明，含有二硫缩醛部分的色酮衍生物可以用作新的抗病毒剂。
• Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives
  作者：Guangcheng Wang、Ming Chen、Jie Qiu、Zhenzhen Xie、Anbai Cao

  DOI：10.1016/j.bmcl.2017.11.047

  日期：2018.1

  designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS. These novel synthetic compounds were evaluated for inhibitory activity against yeast α-glucosidase enzyme. The results of biological test have shown that all tested compounds exhibited excellent to potent inhibitory activity in the range of IC50 = 3.18 ± 0.12–16.59 ± 0.17 μM as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM)

  通过1 H NMR，13 C NMR和HRMS设计，合成和表征了一系列色酮-靛红衍生物6a - 6p。评价了这些新颖的合成化合物对酵母α-葡萄糖苷酶的抑制活性。生物学测试结果表明， 与标准药物阿卡波糖（IC 50  = 817.38±6.27μM）相比，所有测试化合物在IC 50 = 3.18±0.12–16.59±0.17μM范围内均表现出优异至有效的抑制活性。化合物6j（IC 50 （= 3.18±0.12μM），在色酮的7位具有羟基，在isatin的N1位具有4-溴苄基，是该系列中活性最高的化合物。此外，进行了分子对接研究以帮助理解最活跃的类似物与α-葡萄糖苷酶的结合相互作用。这些结果表明这类化合物具有开发抗糖尿病药的潜力。
• [DE] CHROMON-KOMPLEXE<br/>[EN] CHROMONE COMPLEXES<br/>[FR] COMPLEXES DE CHROMONE
  申请人：MERCK PATENT GMBH

  公开号：WO2005097772A1

  公开（公告）日：2005-10-20

  Die Erfindung betrifft Komplexe bestimmter Chromon-Derivate, Zubereitungen, die solche Derivate enthalten, entsprechende Verfahren zur Herstellung der Chromon-Derivate bzw. von diese enthaltenden Zubereitungen und deren Verwendung, insbesondere zur Pflege, Konservierung oder Verbesserung des allgemeinen Zustandes der Haut oder Haare.

  这项发明涉及特定的色酮衍生物复合物，含有这些衍生物的制剂，制备色酮衍生物或含有这些衍生物的制剂的相应方法以及它们的用途，特别是用于皮肤或头发的护理、保养或改善整体状态。