Nucleophilic reactions with the novel condensation product derived from 3-formylchromone and 4-hydroxycoumarin

References

• Venugopala, K. N.; Rashmi, V.; Odhav, B. Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity. Biomed Res. Int. 2013, 2013, 963248–963214. DOI: 10.1155/2013/963248.
   PubMed Web of Science ®Google Scholar
• Stefanachi, A.; Leonetti, F.; Pisani, L.; Catto, M.; Carotti, A. Coumarin: A Natural, Privileged and Versatile Scaffold for Bioactive Compounds. Molecules 2018, 23, 250–284. DOI: 10.3390/molecules23020250.
   PubMed Web of Science ®Google Scholar
• Jadhav, N. H.; Sakate, S. S.; Rasal, N. K.; Shinde, D. R.; Pawar, R. A. Heterogeneously Catalyzed Pechmann Condensation Employing the Tailored Zn0. 925Ti0. 075O NPs: Synthesis of Coumarin. ACS Omega. 2019, 4, 8522–8527. DOI: 10.1021/acsomega.9b00257.
   PubMed Web of Science ®Google Scholar
• Karmakar, S.; Ray, D. Synthesis, Optical Properties, Acid-Base Vapochromism and anti-Counterfeiting of Novel π-Extended Pyridine Fused Coumarins. J. Luminescence 2020, 223, 117229. DOI: 10.1016/j.jlumin.2020.117229.
   Web of Science ®Google Scholar
• Stroea, L.; Murariu, M.; Melinte, V. Fluorescence Quenching Study of New Coumarin-Derived Fluorescent Imidazole-Based Chemosensor. J. Mol. Liquids 2020, 318, 114316. DOI: 10.1016/j.molliq.2020.114316.
   Web of Science ®Google Scholar
• Bakos, É.; Tusnady, G. E.; Nemet, O.; Patik, I.; Magyar, C.; Nemeth, K.; Kele, P.; Özvegy-Laczka, C. Synergistic Transport of a Fluorescent Coumarin Probe Marks Coumarins as Pharmacological Modulators of Organic Anion-Transporting Polypeptide, OATP3A1. Biochem. Pharmacol. 2020, 182, 114250. DOI: 10.1016/j.bcp.2020.114250.
   PubMed Web of Science ®Google Scholar
• Hunagund, U.; Shaikh, F.; Shastri, L. A.; Malimath, G. H.; Naikh, L.; Sunagar, V. S. Synthesis, Characterization, Photo Physical and DFT Studies of Bicoumarin and 3-(3-Benzofuranyl)Coumarin Derivatives. Chem. Data Collect. 2020, 30, 100537. DOI: 10.1016/j.cdc.2020.100537.
   Google Scholar
• Elsenety, M. M.; Elsayed, B. A.; Ibrahem, I. A.; Bedair, M. A. Photophysical, DFT and Molecular Docking Studies of Sm(III) and Eu(III) Complexes of Newly Synthesized Coumarin Ligand. Inorg. Chem. Commun. 2020, 121, 108213. DOI: 10.1016/j.inoche.2020.108213.
   Web of Science ®Google Scholar
• Mishra, S.; Pandey, A.; Manvati, S. Coumarin: An Emerging Antiviral agent. Heliyon. 2020, 6, e03217. DOI: 10.1016/j.heliyon.2020.e03217.
   PubMed Web of Science ®Google Scholar
• Qin, H.-L.; Zhang, Z.-W.; Ravindar, L.; Rakesh, K. P. Antibacterial Activities with the Structure-Activity Relationship of Coumarin Derivatives. Eur. J. Med. Chem. 2020, 207, 112832. DOI: 10.1016/j.ejmech.2020.112832.
   PubMed Web of Science ®Google Scholar
• Sutar, S. M.; Savanur, H. M.; Patil, C.; Pawashe, G. M.; Aridoss, G.; Kim, K. M.; Kalkhambkar, R. G. Synthesis, Molecular Modelling Studies and Antimicrobial Activity of Coumarin and 1-Azacoumarin Linked 1,2,3- Triazole. Chem. Data Collect. 2020, 28, 100480. DOI: 10.1016/j.cdc.2020.100480.
   Google Scholar
• Li, W.-B.; Qiao, X.-P.; Wang, Z.-X.; Wang, S.; Chen, S.-W. Synthesis and Antioxidant Activity of Conjugates of Hydroxytyrosol and Coumarin. Bioorg. Chem. 2020, 105, 104427. DOI: 10.1016/j.bioorg.2020.104427.
   PubMed Web of Science ®Google Scholar
• Liu, Y.-P.; Yan, G.; Xie, Y.-T.; Lin, T.-C.; Zhang, W.; Li, J.; Wu, Y.-J.; Zhou, J.-Y.; Fu, Y.-H. Bioactive Prenylated Coumarins as Potential Anti-inflammatory and Anti-HIV Agents from Clausena lenis. Bioorg. Chem. 2020, 97, 103699. DOI: 10.1016/j.bioorg.2020.103699.
   PubMed Web of Science ®Google Scholar
• Zhang, L.; Xu, Z. Coumarin-Containing Hybrids and Their Anticancer Activities. Eur. J. Med. Chem. 2019, 181, 111587. DOI: 10.1016/j.ejmech.2019.111587.
   PubMed Web of Science ®Google Scholar
• Cruz, L. F.; Figueiredo, G. F.; Pedro, L. P.; Amorin, Y. M.; Andrade, J. T.; Passos, T. F.; Rodrigues, F. F.; Souza, I. L. A.; Gonçalves, T. P. R.; Lima, L. A. R. S.; et al. Umbelliferone (7-Hydroxycoumarin): A Non-toxic Antidiarrheal and Antiulcerogenic Coumarin. Biomed. Pharmacother. 2020, 129, 110432. DOI: 10.1016/j.biopha.2020.110432.
   PubMed Web of Science ®Google Scholar
• Geetha, B. M.; Małecki, J. G.; Alwarsamy, M.; Keri, R. S.; Betageri, V. S.; Budagumpi, S. Coumarin Substituted 4–Aryl–1,2,4–Triazoliumsalts and Their Silver(I) N–Heterocyclic Carbene Complexes: Effects of Counterions on the Antioxidant and Antihaemolytic Properties. J. Mol. Liquids 2020, 316, 113809. DOI: 10.1016/j.molliq.2020.113809.
   Web of Science ®Google Scholar
• Konidala, S. K.; Kotra, V.; Danduga, R. C. S. R.; Kola, P. K. Coumarin-Chalcone Hybrids Targeting Insulin Receptor: Design, Synthesis, Anti-diabetic Activity, and Molecular Docking. Bioorg. Chem. 2020, 104, 104207. DOI: 10.1016/j.bioorg.2020.104207.
   PubMed Web of Science ®Google Scholar
• Shi, D.-H.; Min, W.; Song, M-q.; Si, X.-X.; Li, M.-C.; Zhang, Z-y.; Liu, Y.-W.; Liu, W.-W. Synthesis, Characterization, Crystal Structure and Evaluation of Four Carbazole-Coumarin Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease. J. Mol. Struct. 2020, 1209, 127897. DOI: 10.1016/j.molstruc.2020.127897.
   Web of Science ®Google Scholar
• Gül, D. S.; Ogutcu, H.; Hayvalı, Z. Investigation of Photophysical Behaviors and Antimicrobial Activity of Novel Benzo-15-Crown-5 Substituted Coumarin and Chromone Derivatives. J. Mol. Struct. 2020, 1204, 127569. DOI: 10.1016/j.molstruc.2019.127569.
   Web of Science ®Google Scholar
• Demetgül, C.; Beyazit, N. Synthesis, Characterization and Antioxidant Activity of chitosan-chromone derivatives. Carbohydr. Polym. 2018, 181, 812–817. DOI: 10.1016/j.carbpol.2017.11.074.
   PubMed Web of Science ®Google Scholar
• Roussel, E.; Moreno, A.; Altounian, N.; Philouze, C.; Peres, B.; Thomas, A.; Renaudet, O.; Falson, P.; Boumendjel, A. Chromones Bearing Amino Acid Residues: Easily Accessible and Potent Inhibitors of the Breast Cancer Resistance Protein ABCG2. Eur. J. Med. Chem. 2020, 202, 112503. DOI: 10.1016/j.ejmech.2020.112503.
   PubMed Web of Science ®Google Scholar
• Yu, Z.; Wang, C.; Zheng, W.; Chen, D.; Liu, Y.; Yang, Y.; Wei, J. Anti-inflammatory 5,6,7,8-Tetrahydro-2-(2-Phenylethyl)Chromones from Agarwood of Aquilaria sinensis. Bioorg. Chem. 2020, 99, 103789. DOI: 10.1016/j.bioorg.2020.103789.
   PubMed Web of Science ®Google Scholar
• Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. A Convenient Extension of the Wessely-Moser Rearrangement for the Synthesis of Substituted Alkylaminoflavones as Neuroprotective Agents in Vitro. Bioorg. Med. Chem. Lett. 2000, 10, 835–838. DOI: 10.1016/S0960-894X(00)00110-4.
   PubMed Web of Science ®Google Scholar
• Groweiss, A.; Cardellina, J. H.; Boyd, M. R. HIV-Inhibitory Prenylated Xanthones and Flavones from Maclura tinctoria1. J. Nat. Prod. 2000, 63, 1537–1539. DOI: 10.1021/np000175m.
   PubMed Web of Science ®Google Scholar
• Philip, J. E.; Shahid, M.; Kurup, M. R. P.; Velayudhan, M. P. Metal Based Biologically Active Compounds: Design, Synthesis, DNA Binding and Antidiabetic Activity of 6-methyl-3-Formyl Chromone Derived Hydrazones and Their Metal (II) Complexes. J. Photochem. Photobiol. B. 2017, 175, 178–191. DOI: 10.1016/j.jphotobiol.2017.09.003.
   PubMed Web of Science ®Google Scholar
• Liu, Y.-P.; Yu, X.-M.; Zhang, W.; Wang, T.; Jiang, B.; Tang, H.-X.; Su, Q.-T.; Fu, Y.-H. Prenylated Chromones and Flavonoids from Artocarpus Heterophyllus with Their Potential Antiproliferative and Anti-inflammatory Activities. Bioorg. Chem. 2020, 101, 104030. DOI: 10.1016/j.bioorg.2020.104030.
   PubMed Web of Science ®Google Scholar
• Makhaeva, G. F.; Boltneva, N. P.; Lushchekina, S. V.; Rudakova, E. V.; Serebryakova, O. G.; Kulikova, L. N.; Beloglazkin, A. A.; Borisov, R. S.; Richardson, R. J. Synthesis, Molecular Docking, and Biological Activity of 2-Vinyl Chromones: Toward Selective Butyrylcholinesterase Inhibitors for Potential Alzheimer’s Disease Therapeutics. Bioorg. Med. Chem. 2018, 26, 4716–4725. DOI: 10.1016/j.bmc.2018.08.010.
   PubMed Web of Science ®Google Scholar
• Vijayan, P.; Anitha, P.; Rajeshkumar, M.; Viswanathamurthi, P.; Sugumar, P.; Ponnuswamy, M. N. Enhanced Catalytic Activity Towards One-Pot Hydroxylation of Phenol with Hydrogen Peroxide by Nickel(II) Complex Encompassing 3-Formylchromone-S-Methylisothiosemicarbazone Derivatives. Polyhedron 2017, 124, 77–85. DOI: 10.1016/j.poly.2016.12.031.
   Web of Science ®Google Scholar
• Fouad, R.; Adly, O. M. I. Novel Cu 2+ and Zn2+ Nanocomplexes Drug Based on Hydrazone Ligand Bearings Chromone and Triazine Moieties: Structural, Spectral, DFT, Molecular Docking and Cytotoxic Studies. J. Mol. Struct. 2021, 1225, 129158. DOI: 10.1016/j.molstruc.2020.129158.
   Web of Science ®Google Scholar
• Shebl, M.; Adly, O. M. I.; Taha, A.; Elabd, N. N. Structural Variety in Copper(II) Complexes of 3-Formylchromone: Synthesis, Spectral, Thermal, Molecular Modeling and Biological Studies. J. Mol. Struct. 2017, 1147, 438–451. DOI: 10.1016/j.molstruc.2017.06.085.
   Web of Science ®Google Scholar
• Teimouri, M. B.; Mohammadnia, S. Reaction between Alkyl Isocyanides and 3-Formylchromones in the Presence of Monocyclic Unsaturated Acyl Compounds: Competition Between Friedel-Crafts Acylation and Diels-Alder Cycloaddition. Tetrahedron 2018, 74, 1767–1775. DOI: 10.1016/j.tet.2018.01.054.
   Web of Science ®Google Scholar
• Chen, Z.; Dai, Z.; Zhu, Z.; Yang, X. One-Pot Facile Synthesis of Polysubstituted Pyridines via Tandem Reaction of the Blaise Reaction Intermediates and 3-Formylchromones. Tetrahedron Lett 2017, 58, 1258–1261. DOI: 10.1016/j.tetlet.2017.02.006.
   Web of Science ®Google Scholar
• Barkov, A. Y.; Korotaev, V. Y.; Kutyashev, I. B.; Sosnovskikh, V. Y. Synthesis of Polyfunctionalized Benzophenones via the Reaction of 3-Formylchromones with Tertiary Push-Pull Enamines. Tetrahedron 2016, 72, 2026–2033. DOI: 10.1016/j.tet.2016.03.005.
   Web of Science ®Google Scholar
• Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V. Recyclizations of 3-Formylchromones with Binucleophiles. Tetrahedron 2012, 68, 2743–2757. DOI: 10.1016/j.tet.2012.01.077.
   Web of Science ®Google Scholar
• Ibrahim, M. A.; Ali, T. E.-S.; El-Gohary, N. M.; El-Kazak, A. M. 3-Formylchromones as Diverse Building Blocks in Heterocycles Synthesis. Eur. J. Chem. 2013, 4, 311–328. DOI: 10.5155/eurjchem.4.3.311-328.815.
   Google Scholar
• Ibrahim, M. A.; Badran, A.-S.; El-Gohary, N. M.; Hashiem, S. H. Synthetic Approaches for Heteroannulated Chromones Fused Various Heterocyclic Systems. J. Heterocyclic Chem. 2018, 55, 2315–2324. DOI: 10.3987/rev-20-940.
   Web of Science ®Google Scholar
• Ibrahim, M. A. Ring Transformation of Chromone-3-Carboxamide Under Nucleophilic Conditions. J. Braz. Chem. Soc. 2013, 24, 1754–1763. DOI: 10.5935/0103-5053.20130220.
   Web of Science ®Google Scholar
• El-Kazak, A. M.; El-Gohary, N. M.; Badran, A.-S.; Ibrahim, M. A. Synthesis and Chemical Reactivity of the Novel 3-Chloro-3-(4-Chlorocoumarin-3-yl)Prop-2-Enal. Tetrahedron 2019, 75, 3923–3932. DOI: 10.1016/j.tet.2019.06.013.
   Web of Science ®Google Scholar
• Ibrahim, M. A.; Abdel-Hamed, M. A.-M.; El-Gohary, N. M. A. New Synthetic Approach for the Bioactive Heteroaryl Thiazolidine-2,4-Diones. J. Braz. Chem. Soc. 2011, 22, 1130–1139. DOI: 10.1590/S0103-50532011000600019.
   Web of Science ®Google Scholar
• Nohara, A.; Umetani, T.; Sanno, Y. Studies on Antianaphylactic Agents—I: A Facile Synthesis of 4-Oxo-4H-1-Benzopyran-3-Carboxaldehydes by Vilsmeier Reagents. Tetrahedron 1974, 30, 3553–3561. . DOI: 10.1016/S0040-4020(01)97034-6.
   Web of Science ®Google Scholar