Coumarin-Fused Coumarin: Antioxidant Story from N, N -Dimethylamino and Hydroxyl Groups

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 13, 2015, Pages 3516-3523

  Xi, Gao Lei ^a   Liu, Zai Qun ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

antioxidant; coumarin fused coumarin; DNA oxidation; free radical

Indexed keywords

DNA; FREE RADICALS; FUNCTIONAL GROUPS; OXIDATION; RATE CONSTANTS; SCAFFOLDS;

COUMARIN-FUSED COUMARIN; DNA OXIDATION; GALVINOXYL RADICALS; HIGH ACTIVITY; HYDROXYL GROUPS; INDUCED OXIDATIONS; INHIBITORY EFFECT; SYNTHETIC COMPOUNDS;

ANTIOXIDANTS;

2,2'-AZOBIS(2-AMIDINOPROPANE); AMIDINE; ANTIOXIDANT; COPPER; COUMARIN; COUMARIN DERIVATIVE; DNA; FREE RADICAL; GLUTATHIONE; HYDROXYL RADICAL; OXIDIZING AGENT; SCAVENGER;

CHEMISTRY; OXIDATION REDUCTION REACTION;

AMIDINES; ANTIOXIDANTS; COPPER; COUMARINS; DNA; FREE RADICAL SCAVENGERS; FREE RADICALS; GLUTATHIONE; HYDROXYL RADICAL; OXIDANTS; OXIDATION-REDUCTION;

EID: 84926430258     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b00399     Document Type: Article

References (30)

1. Sandhu, S.; Bansal, Y.; Silakari, O.; Bansal, G. Coumarin hybrids as novel therapeutic agents Bioorg. Med. Chem. 2014, 22, 3806 - 3814
2. Hamulakova, S.; Janovec, L.; Hrabinova, M.; Spilovska, K.; Korabecny, J.; Kristian, P.; Kuca, K.; Imrich, J. Synthesis and biological evaluation of novel tacrine derivatives and tacrine-coumarin hybrids as cholinesterase inhibitors J. Med. Chem. 2014, 57, 7073 - 7084
3. Roussakia, M.; Zelianaios, K.; Kavetsou, E.; Hamilakis, S.; Hadjipavlou-Litina, D.; Kontogiorgis, C.; Liargkova, T.; Detsi, A. Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity Bioorg. Med. Chem. 2014, 22, 6586 - 6594
4. Renuka, N.; Kumar, K. A. Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents Bioorg. Med. Chem. Lett. 2013, 23, 6406 - 6409
5. Pratap, R.; Ram, V. J. Natural and synthetic chromenes, fused chromenes, and versatility of dihydro benzo[ h ]chromenes in organic synthesis Chem. Rev. 2014, 114, 10476 - 10526
6. Zheng, K.; Lin, W.; Tan, L.; Chen, H.; Cui, H. A unique carbazole-coumarin fused two-photon platform: Development of a robust two-photon fluorescent probe for imaging carbon monoxide in living tissues Chem. Sci. 2014, 5, 3439 - 3448
7. Tasior, M.; Poronik, Y. M.; Vakuliuk, O.; Sadowski, B.; Karczewski, M.; Gryko, D. T. V-Shaped bis-coumarins: Synthesis and optical properties J. Org. Chem. 2014, 79, 8723 - 8732
8. Pardo-Jiménez, V.; Barrientos, C.; Pérez-Cruz, K.; Navarrete-Encina, P. A.; Olea-Azar, C.; Nuñez-Vergara, L. J.; Squella, J. A. Synthesis and electrochemical oxidation of hybrid compounds: Dihydropyridine-fused coumarins Electrochim. Acta 2014, 125, 457 - 464
9. Xi, G.-L.; Liu, Z.-Q. Coumestan inhibits radical-induced oxidation of DNA: Is hydroxyl a necessary functional group? J. Agric. Food Chem. 2014, 62, 5636 - 5642
10. Kim, Y.; Moon, Y.; Kang, D.; Hong, S. Synthesis of heterocyclic-fused benzopyrans via the Pd(II)-catalyzed C-H alkenylation/C-O cyclization of flavones and coumarins Org. Biomol. Chem. 2014, 12, 3413 - 3422
11. Veselinović, J. B.; Veselinović, A. M.; Vitnik, Z. J.; Vitnik, V. D.; Nikolić, G. M. Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies Chem.-Biol. Interact. 2014, 214, 49 - 56
12. Tanemossu, S. A. F.; Franke, K.; Arnold, N.; Schmidt, J.; Wabo, H. K.; Tane, P.; Wessjohann, L. A. Rare biscoumarin derivatives and flavonoids from Hypericum riparium Phytochemistry 2014, 105, 171 - 177
13. Chen, J.; Liu, W.; Zhou, B.; Niu, G.; Zhang, H.; Wu, J.; Wang, Y.; Ju, W.; Wang, P. Coumarin- and rhodamine-fused deep red fluorescent dyes: Synthesis, photophysical properties, and bioimaging in vitro J. Org. Chem. 2013, 78, 6121 - 6130
14. Su, H.; Gornitsky, M.; Velly, A. M.; Yu, H.; Benarroch, M.; Schipper, H. M. Salivary DNA, lipid, and protein oxidation in nonsmokers with periodontal disease Free Radical Biol. Med. 2009, 46, 914 - 921
15. Miura, T.; Fujioka, S.; Iwasaki, H.; Ozeki, M.; Kojima, N.; Yamashita, M. Skeleton transformation of α-pyrone induced by 5-aryl substituent into ring-fused dihydrofuran Tetrahedron Lett. 2014, 55, 1536 - 1539
16. Karthik, G.; Rajasekaran, T.; Sridhar, B.; Reddy, B. V. S. Highly regio- and diastereoselective three-component reaction of acyclic/cyclic donor-acceptor carbenoids for the synthesis of angularly fused furocoumarins and spirooxindolylfurocoumarins Tetrahedron 2014, 70, 8148 - 8154
17. 2 productions in RAW264.7 macrophages Bioorg. Med. Chem. Lett. 2014, 24, 571 - 575
18. Kanchithalaivan, S.; Sumesh, R. V.; Kumar, R. R. Ultrasound-assisted sequential multicomponent strategy for the combinatorial synthesis of novel coumarin hybrids ACS Comb. Sci. 2014, 16, 566 - 572
19. Khoobi, M.; Ramazani, A.; Mahdavi, M.; Foroumadi, A.; Emami, S.; Joo, S. W.; ͆lepokura, K.; Lis, T.; Shafiee, A. Efficient solvent-free synthesis of benzothiazine-fused pyrrolo[3,4- c ]coumarins: Cycloaddition reactions between coumarin-based dihydrobenzothiazoles and isocyanides Helv. Chim. Acta 2014, 97, 847 - 853
20. Yamamoto, Y.; Matsui, K.; Shibuya, M. Tandem Ruthenium-catalyzed transfer-hydrogenative cyclization/intramolecular Diels-Alder reaction of enediynes affording dihydrocoumarin-fused polycycles Org. Lett. 2014, 16, 1806 - 1809
21. Moon, Y.; Kim, Y.; Hong, H.; Hong, S. Synthesis of heterocyclic-fused benzofurans via C-H functionalization of flavones and coumarins Chem. Commun. 2013, 49, 8323 - 8325
22. Xi, G.-L.; Liu, Z.-Q. Solvent-free Povarov reaction for synthesizing ferrocenyl quinolines: Antioxidant abilities deriving from ferrocene moiety Eur. J. Med. Chem. 2014, 86, 759 - 768
23. Mertens, M. D.; Hinz, S.; Müller, C. E.; Gütschow, M. Alkynyl-coumarinyl ethers as MAO-B inhibitors Bioorg. Med. Chem. 2014, 22, 1916 - 1928
24. Speisky, H.; Gómez, M.; Burgos-Bravo, F.; López-Alarcón, C.; Jullian, C.; Olea-Azar, C.; Aliaga, M. E. Generation of superoxide radicals by copper-glutathione complexes: Redox-consequences associated with their interaction with reduced glutathione Bioorg. Med. Chem. 2009, 17, 1803 - 1810
25. Zhu, B. Z.; Kitrossky, N.; Chevion, M. Evidence for production of hydroxyl radicals by pentachlorophenol metabolites and hydrogen peroxide: A metal-independent organic Fenton reaction Biochem. Biophys. Res. Commun. 2000, 270, 942 - 946
26. Sugden, K. D.; Wetterhahn, K. E. Direct and hydrogen peroxide-induced chromium(V) oxidation of deoxyribose in single-stranded and double-stranded calf thymus DNA Chem. Res. Toxicol. 1997, 10, 1397 - 1406
27. Wang, Q.; Qian, Y.-P.; Dai, F.; Lu, D.-L.; Yan, W.-J.; Chen, Y.; Zhou, B. ortho -Dihydroxy chalcones as cupric ion-dependent prooxidants: Activity and mechanisms Food Chem. 2013, 141, 1259 - 1266
28. Bowry, V. W.; Stocker, R. Tocopherol-mediated peroxidation: The prooxidation effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein J. Am. Chem. Soc. 1993, 115, 6029 - 6044
29. Doulou, I.; Kontogiorgis, C.; Koumbis, A. E.; Evgenidou, E.; Hadjipavlou-Litina, D.; Fylaktakidou, K. C. Synthesis of stable aromatic and heteroaromatic sulfonyl-amidoximes and evaluation of their antioxidant and lipid peroxidation activity Eur. J. Med. Chem. 2014, 80, 145 - 153
30. Wang, R.; Liu, Z.-Q. Solvent-free and catalyst-free Biginelli reaction to synthesize ferrocenoyl dihydropyrimidine and kinetic method to express radical-scavenging ability J. Org. Chem. 2012, 77, 3952 - 3958