二苯并吡喃酮及其衍生物的合成研究进展
Research Progress on the Synthesis of Dibenzopyranone and Its Derivatives
DOI: 10.12677/jocr.2025.132014, PDF,    国家自然科学基金支持
作者: 张虎虎*, 薛梓超, 陈兴楠, 樊晓辉*:兰州交通大学化学化工学院,甘肃 兰州
关键词: 二苯并吡喃酮三环骨架生物活性药理活性 Dibenzopyranone Tricyclic Framework Biological Activity Pharmacological Activity
摘要: 二苯并吡喃酮及其衍生物是一类具有重要生物活性和应用价值的杂环化合物,广泛存在于天然产物(如黄酮类、香豆素类化合物)中,并展现出抗氧化、抗炎、抗菌及抗肿瘤等特性。近年来,其合成研究已成为有机领域的热点之一。本文系统综述了此类化合物在药物化学和材料科学中的应用潜力,以及合成策略与研究进展,重点讨论了传统合成路线和近年来发展的绿色合成方法。指出了当前合成领域中存在的挑战,并对未来研究方向进行了展望,为二苯并吡喃酮化合物的合成及应用研究提供参考。
Abstract: Dibenzopyranone and its derivatives are a class of heterocyclic compounds with important biological activity and application value, widely present in natural products such as flavonoids and coumarins, and exhibiting antioxidant, anti-inflammatory, antibacterial, and anti-tumor properties. In recent years, its synthesis research has become one of the hotspots in the organic field. This article systematically reviews the potential applications of such compounds in medicinal chemistry and materials science, as well as their synthesis strategies and research progress, with a focus on traditional synthesis routes and green synthesis methods developed in recent years. The challenges in the current synthesis field were pointed out, and future research directions were discussed, providing reference for the synthesis and application research of dibenzopyranone compounds.
文章引用:张虎虎, 薛梓超, 陈兴楠, 樊晓辉. 二苯并吡喃酮及其衍生物的合成研究进展[J]. 有机化学研究, 2025, 13(2): 133-145. https://doi.org/10.12677/jocr.2025.132014

参考文献

[1] Tanahashi, T., Kuroishi, M., Kuwahara, A., Nagakura, N. and Hamada, N. (1997) Four Phenolics from the Cultured Lichen Mycobiont of Graphis Scripta Var. Pulverulenta. Chemical and Pharmaceutical Bulletin, 45, 1183-1185. [Google Scholar] [CrossRef
[2] Tanahashi, T., Takenaka, Y., Nagakura, N. and Hamada, N. (2003) 6H-Dibenzo[b,d]Pyran-6-One Derivatives from the Cultured Lichen Mycobionts of Graphis Spp. and Their Biosynthetic Origin. Phytochemistry, 62, 71-75. [Google Scholar] [CrossRef] [PubMed]
[3] Liang, D., Luo, H., Liu, Y., Hao, Z., Wang, Y., Zhang, C., et al. (2013) Lysilactones A-C, Three 6H-Dibenzo[b,d]Pyran-6-One Glycosides from Lysimachia clethroides, Total Synthesis of Lysilactone A. Tetrahedron, 69, 2093-2097. [Google Scholar] [CrossRef
[4] Lou, J., Fu, L., Peng, Y. and Zhou, L. (2013) Metabolites from Alternaria Fungi and Their Bioactivities. Molecules, 18, 5891-5935. [Google Scholar] [CrossRef] [PubMed]
[5] Coghlan, M.J., Kym, P.R., Elmore, S.W., Wang, A.X., Luly, J.R., Wilcox, D., et al. (2001) Synthesis and Characterization of Non-Steroidal Ligands for the Glucocorticoid Receptor: Selective Quinoline Derivatives with Prednisolone-Equivalent Functional Activity. Journal of Medicinal Chemistry, 44, 2879-2885. [Google Scholar] [CrossRef] [PubMed]
[6] Murakami-Nakai, C., Maeda, N., Yonezawa, Y., Kuriyama, I., Kamisuki, S., Takahashi, S., et al. (2004) The Effects of Dehydroaltenusin, a Novel Mammalian DNA Polymerase Α Inhibitor, on Cell Proliferation and Cell Cycle Progression. Biochimica et Biophysica Acta (BBA)-General Subjects, 1674, 193-199. [Google Scholar] [CrossRef] [PubMed]
[7] Zhang, H., Huang, W., Song, Y., Chen, J. and Tan, R. (2005) Four 6H‐Dibenzo[b,d]Pyran-6-One Derivatives Produced by the Endophyte Cephalosporium acremonium IFB-E007. Helvetica Chimica Acta, 88, 2861-2864. [Google Scholar] [CrossRef
[8] Mao, Z., Sun, W., Fu, L., Luo, H., Lai, D. and Zhou, L. (2014) Natural Dibenzo-α-Pyrones and Their Bioactivities. Molecules, 19, 5088-5108. [Google Scholar] [CrossRef] [PubMed]
[9] Seeram, N.P., Aronson, W.J., Zhang, Y., Henning, S.M., Moro, A., Lee, R., et al. (2007) Pomegranate Ellagitannin-Derived Metabolites Inhibit Prostate Cancer Growth and Localize to the Mouse Prostate Gland. Journal of Agricultural and Food Chemistry, 55, 7732-7737. [Google Scholar] [CrossRef] [PubMed]
[10] Wu, S., Wen, Y., Li, X., Zhao, Y., Zhao, Z. and Hu, J. (2009) Chemical Constituents from the Fruits of Sonneratia caseolaris and Sonneratia ovata (Sonneratiaceae). Biochemical Systematics and Ecology, 37, 1-5. [Google Scholar] [CrossRef
[11] Adams, L.S., Zhang, Y., Seeram, N.P., Heber, D. and Chen, S. (2010) Pomegranate Ellagitannin-Derived Compounds Exhibit Antiproliferative and Antiaromatase Activity in Breast Cancer Cells in Vitro. Cancer Prevention Research, 3, 108-113. [Google Scholar] [CrossRef] [PubMed]
[12] Bialonska, D., Kasimsetty, S.G., Khan, S.I. and Ferreira, D. (2009) Urolithins, Intestinal Microbial Metabolites of Pomegranate Ellagitannins, Exhibit Potent Antioxidant Activity in a Cell-Based Assay. Journal of Agricultural and Food Chemistry, 57, 10181-10186. [Google Scholar] [CrossRef] [PubMed]
[13] González-Barrio, R., Truchado, P., Ito, H., Espín, J.C. and Tomás-Barberán, F.A. (2011) UV and MS Identification of Urolithins and Nasutins, the Bioavailable Metabolites of Ellagitannins and Ellagic Acid in Different Mammals. Journal of Agricultural and Food Chemistry, 59, 1152-1162. [Google Scholar] [CrossRef] [PubMed]
[14] Babich, O.O., Skrypnik, L.N. and Pungin, A.V. (2021) In Vitro Study of the Antioxidant Activity of Extracts from Dried Biomass of Callus, Cell Suspension, and Root Cultures. IOP Conference Series: Earth and Environmental Science, 689, Article 012029. [Google Scholar] [CrossRef
[15] Pozzo, L., Grande, T., Raffaelli, A., Longo, V., Weidner, S., Amarowicz, R., et al. (2023) Characterization of Antioxidant and Antimicrobial Activity and Phenolic Compound Profile of Extracts from Seeds of Different Vitis Species. Molecules, 28, Article 4924. [Google Scholar] [CrossRef] [PubMed]
[16] Doyle, B. and Griffiths, L.A. (1980) The Metabolism of Ellagic Acid in the Rat. Xenobiotica, 10, 247-256. [Google Scholar] [CrossRef] [PubMed]
[17] Cerdá, B., Periago, P., Espín, J.C. and Tomás-Barberán, F.A. (2005) Identification of Urolithin a as a Metabolite Produced by Human Colon Microflora from Ellagic Acid and Related Compounds. Journal of Agricultural and Food Chemistry, 53, 5571-5576. [Google Scholar] [CrossRef] [PubMed]
[18] Gu, W. (2009) Bioactive Metabolites from Alternaria brassicicola ML-P08, an Endophytic Fungus Residing in Malus Halliana. World Journal of Microbiology and Biotechnology, 25, 1677-1683. [Google Scholar] [CrossRef
[19] Mizushina, Y., Maeda, N., Kuriyama, I. and Yoshida, H. (2011) Dehydroaltenusin Is a Specific Inhibitor of Mammalian DNA Polymerase Α. Expert Opinion on Investigational Drugs, 20, 1523-1534. [Google Scholar] [CrossRef] [PubMed]
[20] Ishimoto, H., Tai, A., Yoshimura, M., Amakura, Y., Yoshida, T., Hatano, T., et al. (2012) Antioxidative Properties of Functional Polyphenols and Their Metabolites Assessed by an ORAC Assay. Bioscience, Biotechnology, and Biochemistry, 76, 395-399. [Google Scholar] [CrossRef] [PubMed]
[21] Piwowarski, J., Granica, S. and Kiss, A. (2014) Influence of Gut Microbiota-Derived Ellagitanninsʼ Metabolites Urolithins on Pro-Inflammatory Activities of Human Neutrophils. Planta Medica, 80, 887-895. [Google Scholar] [CrossRef] [PubMed]
[22] Bobowska, A., Granica, S., Filipek, A., Melzig, M.F., Moeslinger, T., Zentek, J., et al. (2021) Comparative Studies of Urolithins and Their Phase II Metabolites on Macrophage and Neutrophil Functions. European Journal of Nutrition, 60, 1957-1972. [Google Scholar] [CrossRef] [PubMed]
[23] Zhou, Q.J., Worm, K. and Dolle, R.E. (2004) 10-Hydroxy-10,9-Boroxarophenanthrenes: Versatile Synthetic Intermediates to 3,4-Benzocoumarins and Triaryls. The Journal of Organic Chemistry, 69, 5147-5149. [Google Scholar] [CrossRef] [PubMed]
[24] Vishnumurthy, K. and Makriyannis, A. (2010) Novel and Efficient One-Step Parallel Synthesis of Dibenzopyranones via Suzuki-Miyaura Cross Coupling. Journal of Combinatorial Chemistry, 12, 664-669. [Google Scholar] [CrossRef] [PubMed]
[25] Luo, J., Lu, Y., Liu, S., Liu, J. and Deng, G. (2011) Efficient One-Pot Synthesis of Dibenzopyranones via a Decarboxylative Cross-Coupling and Lactonization Sequence. Advanced Synthesis & Catalysis, 353, 2604-2608. [Google Scholar] [CrossRef
[26] Xiao, Q., Zhang, Y. and Wang, J. (2012) Diazo Compounds and N-Tosylhydrazones: Novel Cross-Coupling Partners in Transition-Metal-Catalyzed Reactions. Accounts of Chemical Research, 46, 236-247. [Google Scholar] [CrossRef] [PubMed]
[27] Singha, R., Roy, S., Nandi, S., Ray, P. and Ray, J.K. (2013) Palladium-Catalyzed One-Pot Suzuki-Miyaura Cross Coupling Followed by Oxidative Lactonization: A Novel and Efficient Route for the One-Pot Synthesis of Benzo[c]Chromene-6-Ones. Tetrahedron Letters, 54, 657-660. [Google Scholar] [CrossRef
[28] Singha, R., Dhara, S., Ghosh, M. and Ray, J.K. (2015) Copper Catalyzed Room Temperature Lactonization of Aromatic C-H Bond: A Novel and Efficient Approach for the Synthesis of Dibenzopyranones. RSC Advances, 5, 8801-8805. [Google Scholar] [CrossRef
[29] Zhang, Z., Gao, Y., Liu, Y., Li, J., Xie, H., Li, H., et al. (2015) Organocatalytic Aerobic Oxidation of Benzylic Sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst. Organic Letters, 17, 5492-5495. [Google Scholar] [CrossRef] [PubMed]
[30] Suárez-Meneses, J.V., Oukhrib, A., Gouygou, M., Urrutigoïty, M., Daran, J.-C., Cordero-Vargas, A., et al. (2016) [N,P]-pyrrole PdCl2 Complexes Catalyzed the Formation of Dibenzo-α-Pyrone and Lactam Analogues. Dalton Transactions, 45, 9621-9630. [Google Scholar] [CrossRef] [PubMed]
[31] Zhang, J., Shi, D., Zhang, H., Xu, Z., Bao, H., Jin, H., et al. (2017) Synthesis of Dibenzopyranones and Pyrazolobenzopyranones through Copper(0)/Selectfluor System-Catalyzed Double CH Activation/Oxygen Insertion of 2-Arylbenzaldehydes and 5-Arylpyrazole-4-Carbaldehydes. Tetrahedron, 73, 154-163. [Google Scholar] [CrossRef
[32] Ortiz Villamizar, M.C., Zubkov, F.I., Puerto Galvis, C.E., Vargas Méndez, L.Y. and Kouznetsov, V.V. (2017) The Study of Metal-Free and Palladium-Catalysed Synthesis of Benzochromenes via Direct C-H Arylation Using Unactivated Aryl Benzyl Ethers Derived from Essential Oils as Raw Materials. Organic Chemistry Frontiers, 4, 1736-1744. [Google Scholar] [CrossRef
[33] Fu, L., Li, S., Cai, Z., Ding, Y., Guo, X., Zhou, L., et al. (2018) Ligand-Enabled Site-Selectivity in a Versatile Rhodium(II)-Catalysed Aryl C-H Carboxylation with CO2. Nature Catalysis, 1, 469-478. [Google Scholar] [CrossRef
[34] Luo, S., Li, L., Yang, Q. and Jia, Z. (2018) Organocatalytic Electrochemical C-H Lactonization of Aromatic Carboxylic Acids. Synthesis, 50, 2924-2929. [Google Scholar] [CrossRef
[35] Khosravi, K. and Naserifar, S. (2019) Urea-2,2-Dihydroperoxypropane as a Novel and High Oxygen Content Alternative to Dihydroperoxypropane in Several Oxidation Reactions. ChemistrySelect, 4, 1576-1585. [Google Scholar] [CrossRef
[36] Luo, Z., Gao, Z., Song, Z., Han, Y. and Ye, S. (2019) Visible Light Mediated Oxidative Lactonization of 2-Methyl-1,1′-Biaryls for the Synthesis of Benzocoumarins. Organic & Biomolecular Chemistry, 17, 4212-4215. [Google Scholar] [CrossRef] [PubMed]
[37] Shirase, S., Tamaki, S., Shinohara, K., Hirosawa, K., Tsurugi, H., Satoh, T., et al. (2020) Cerium(IV) Carboxylate Photocatalyst for Catalytic Radical Formation from Carboxylic Acids: Decarboxylative Oxygenation of Aliphatic Carboxylic Acids and Lactonization of Aromatic Carboxylic Acids. Journal of the American Chemical Society, 142, 5668-5675. [Google Scholar] [CrossRef] [PubMed]
[38] Chao, M., Wang, H., Zhang, H., Zhong, F., Luo, Z., Wu, F., et al. (2022) Cobalt (II)-Catalyzed Oxidation of 2-Aryl Benzoic Acids to Access Biaryl Lactones. Applied Organometallic Chemistry, 36, e6809. [Google Scholar] [CrossRef
[39] Natarajan, P., Pooja and Meena (2023) 2-Arylbenzyl Methyl Ethers as Precursors for the Tandem Synthesis of Benzo[c]Coumarins over Heterogeneous Visible-Light Photoredox Catalysis with Graphitic Carbon Nitride (g-C3N4). Asian Journal of Organic Chemistry, 12, e202200643. [Google Scholar] [CrossRef
[40] Shi, G., Wang, Y., He, M., Yu, X. and Bao, M. (2023) 2,7-Dinitrophenanthrene-9,10-Dione as a Photosensitizer for the Dehydrogenative Lactonization of 2-Arylbenzoic Acids. Organic Chemistry Frontiers, 10, 2429-2433. [Google Scholar] [CrossRef
[41] Fang, M., Shang, P., Huang, H., Sun, J. and Han, Z. (2024) Synthesis of Lactones via Electrochemical Sequential Oxidative Process. European Journal of Organic Chemistry, 27, e202400557. [Google Scholar] [CrossRef