Oxidative stress and neurodegenerative diseases: Looking for a therapeutic solution inspired on benzopyran chemistry

Current Topics in Medicinal Chemistry

Volumn 15, Issue 5, 2015, Pages 432-445

  Gaspar, Alexandra ^a   Milhazes, Nuno ^a,b   Santana, Lourdes ^c   Uriarte, Eugenio ^c   Borges, Fernanda ^a   Matos, Maria João ^a,c  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY INSTITUTE OF HEALTH SCIENCES IUCS   (Portugal)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Alzheimer s disease; Chromones; Coumarins; Neurodegenerative diseases; Oxidative stress; Parkinson s disease

Indexed keywords

4 HYDROXYCOUMARIN; ACENOCOUMAROL; ACETYLCHOLINE; ACETYLCHOLINESTERASE; ALPHA SYNUCLEIN; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; BENSERAZIDE; BENZIMIDAZOLE; BENZOPYRAN DERIVATIVE; BETA SECRETASE INHIBITOR; BROMOCRIPTINE; CARBIDOPA; CATECHIN; CELL NUCLEUS DNA; CHROMONE DERIVATIVE; COUMARIN DERIVATIVE; DONEPEZIL; EBSELEN; LADOSTIGIL; LEVODOPA; PHENPROCOUMON; PRAMIPEXOLE; RASAGILINE; RIVASTIGMINE; ROPINIROLE; SELEGILINE; TACRINE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; WARFARIN; ANTIOXIDANT; DOPAMINE RECEPTOR STIMULATING AGENT; MONOAMINE OXIDASE INHIBITOR; NEUROPROTECTIVE AGENT; REACTIVE OXYGEN METABOLITE;

ALZHEIMER DISEASE; ANGELICA; ANTIOXIDANT ACTIVITY; ARTICLE; DEGENERATIVE DISEASE; DPPH RADICAL SCAVENGING ASSAY; HUMAN; HYDROPHOBICITY; NEUROPROTECTION; OXIDATIVE STRESS; PARKINSON DISEASE; SUBSTANTIA NIGRA; ANTAGONISTS AND INHIBITORS; DRUG EFFECTS; METABOLISM; OXIDATION REDUCTION REACTION; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALZHEIMER DISEASE; ANTIOXIDANTS; CHROMONES; COUMARINS; DOPAMINE AGONISTS; HUMANS; MONOAMINE OXIDASE INHIBITORS; NEUROPROTECTIVE AGENTS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PARKINSON DISEASE; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84930908241     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026614666141229124141     Document Type: Article

References (189)

1. Halliwell, B. Role of free radicals in the neurodegenerative diseases: Therapeutic implications for antioxidant treatment. Drugs aging, 2001, 18(9), 685-716.
2. Barnham, K. J.; Masters, C. L.; Bush, A. I. Neurodegenerative diseases and oxidative stress. Nat. Rev. Drug Discov., 2004, 3(3), 205-214.
3. Reuter, S.; Gupta, S. C.; Chaturvedi, M. M.; Aggarwal, B. B. Oxidative stress, inflammation, and cancer: How are they linked? Free Rad. Biol. Med., 2010, 49(11), 1603-1616.
4. Uttara, B.; Singh, A. V.; Zamboni, P.; Mahajan, R. T. Oxidative stress and neurodegenerative diseases: A review of upstream and downstream antioxidant therapeutic options. Curr. Neuropharmacol., 2009, 7(1), 65-74.
5. Zhao, B. Natural antioxidants for neurodegenerative diseases. Curr. Neurobiol., 2005, 31(1-3), 283-293.
6. Dauer, W.; Przedborski, S. Parkinson's disease: Mechanisms and models. Neuron., 2003, 39(6), 889-909.
7. Olanow, C. W.; McNaught, K. S. Ubiquitin-proteasome system and Parkinson's disease. Mov. Disord., 2006, 21(11), 1806-1823.
8. Meredith, G. E.; Totterdell, S.; Beales, M.; Meshul, C. K. Impaired glutamate homeostasis and programmed cell death in a chronic MPTP mouse model of Parkinson's disease. Exp. Neurol., 2009, 219(1), 334-340.
9. Querfurth, H. W.; LaFerla, F. M. Mechanisms of disease Alzheimer's disease. N. Engl. J. Med., 2010, 362(4), 329-344.
10. Citron, M. Alzheimer's disease: Strategies for disease modification. Nat. Rev. Drug Discov., 2010, 9(5), 387-398.
11. Scarpini, E.; Scheltens, P.; Feldman, H. Treatment of Alzheimer's disease: Current status and new perspectives. Lancet Neurol., 2003, 2(9), 539-547.
12. Pisani, L.; Catto, M.; Giangreco, I.; Leonetti, F.; Nicolotti, O.; Stefanachi, A.; Cellamare, S.; Carotti, A. Design, synthesis, and biological evaluation of coumarin derivatives tethered to an edrophonium-like fragment as highly potent and selective dual binding site acetylcholinesterase inhibitors. ChemMedChem, 2010, 5(9), 1616-1630.
13. Anand, P.; Singh, B. A review on cholinesterase inhibitors for Alzheimer's disease. Arch. Pharm. Res., 2013, 36(4), 375-399.
14. Russo, P.; Frustaci, A.; Del Bufalo, A.; Fini, M.; Cesario, A. From traditional european medicine to discovery of new drug candidates for the treatment of dementia and Alzheimer's disease: Acetylcholinesterase inhibitors. Curr. Med. Chem., 2013, 20(8), 976-983.
15. Mehta, M.; Adem, A.; Sabbagh, M. New acetylcholinesterase inhibitors for Alzheimer's disease. Int. J. Alzheimers Dis., 2012, 2012, 8.
16. Swomley, A. M.; Forster, S.; Keeney, J. T.; Triplett, J.; Zhang, Z.; Sultana, R.; Butterfield, D. A. Abeta, oxidative stress in Alzheimer disease: Evidence based on proteomics studies. Biochim. Biophys. Acta, 2014, 1842(8), 1248-1257.
17. Pohanka, M. Alzheimer's disease and oxidative stress: A review. Curr. Med. Chem., 2014, 21(3), 356-364.
18. Plaza, M.; Pozzo, T.; Liu, J.; Gulshan, A. K. Z.; Turner, C.; Nordberg, K. E. Substituent effects on in vitro antioxidizing properties, stability, and solubility in flavonoids. J. Agric. Food Chem., 2014, 62(15), 3321-3333.
19. Wang, X. L.; Wang, W.; Li, L.; Perry, G.; Lee, H. G.; Zhu, X. Oxidative stress and mitochondrial dysfunction in Alzheimer's disease. Biochim. Biophys. Acta, 2014, 1842(8), 1240-1247.
20. Nunomura, A.; Perry, G.; Aliev, G.; Hirai, K.; Takeda, A.; Balraj, E. K.; Jones, P. K.; Ghanbari, H.; Wataya, T.; Shimohama, S.; Chiba, S.; Atwood, C. S.; Petersen, R. B.; Smith, M. A. Oxidative damage is the earliest event in Alzheimer disease. J. Neuropathol. Exp. Neurol., 2001, 60(8), 759-767.
21. Greenough, M. A.; Camakaris, J.; Bush, A. I. Metal dyshomeostasis and oxidative stress in Alzheimer's disease. Neurochem. Int., 2013, 62(5), 540-555.
22. Butterfield, D. A.; Castegna, A.; Lauderback, C. M.; Drake, J. Evidence that amyloid beta-peptide-induced lipid peroxidation and its sequelae in Alzheimer's disease brain contribute to neuronal death. Neurobiol. Aging, 2002, 23(5), 655-664.
23. Saura, J.; Luque, J. M.; Cesura, A. M.; Da Prada, M.; Chan-Palay, V.; Huber, G.; Loffler, J.; Richards, J. G. Increased monoamineoxidase-B activity in plaque-associated astrocytes of Alzheimer brains revealed by quantitative enzyme autoradiography. Neuroscience, 1994, 62(1), 15-30.
24. Piazzi, L.; Cavalli, A.; Colizzi, F.; Belluti, F.; Bartolini, M.; Mancini, F.; Recanatini, M.; Andrisano, V.; Rampa, A. Multi-targetdirected coumarin derivatives: hAChE and BACE1 inhibitors as potential anti-Alzheimer compounds. Bioorg. Med. Chem. Lett., 2008, 18(1), 423-426.
25. Mohamed, T.; Rao, P. P. N. Alzheimer's disease: Emerging trends in small molecule therapies. Curr. Med. Chem., 2011, 18(28), 4299-4320.
26. Rampa, A.; Bartolini, M.; Bisi, A.; Belluti, F.; Gobbi, S.; Andrisano, V.; Ligresti, A.; Di Marzo, V. The first dual ChE/FAAH inhibitors: New perspectives for Alzheimer's disease? Med. Chem. Lett., 2012, 3(3), 182-186.
27. Youdim, M. B.; Bar, Am. O.; Yogev-Falach, M.; Weinreb, O.; Maruyama, W.; Naoi, M.; Amit, T. Rasagiline: Neurodegeneration, neuroprotection, and mitochondrial permeability transition. J. Neuroscience Res., 2005, 79(1-2), 172-179.
28. Viayna, E.; Sabate, R.; Munoz-Torrero, D. Dual inhibitors of αβ-amyloid aggregation and acetylcholinesterase as multi-target anti-Alzheimer drug candidates. Curr. Top. Med. Chem., 2013, 13(15), 1820-1842.
29. Tailor, N.; Sharma, M. Antioxidant hybrid compounds: A promising therapeutic intervention in oxidative stress induced diseases. Mini Rev. Med. Chem., 2013, 13(2), 280-297.
30. Luo, Z. H.; Sheng, J.; Sun, Y.; Lu, C.; Yan, J.; Liu, A.; Luo, H. B.; Huang, L.; Li, X. Synthesis and evaluation of multi-target-directed ligands against Alzheimer's disease based on the fusion of donepezil and ebselen. J. Med. Chem., 2013, 56(22), 9089-9099.
31. Lu, C. J.; Guo, Y.; Li, J.; Yao, M.; Liao, Q.; Xie, Z.; Li, X. Design, synthesis, and evaluation of resveratrol derivatives as A beta(1-42) aggregation inhibitors, antioxidants, and neuroprotective agents. Bioorg. Med. Chem. Lett., 2012, 22(24), 7683-7687.
32. Cools, R. Dopaminergic modulation of cognitive functionimplications for l-DOPA treatment in Parkinson's disease. Neurosci. Biobehav. Rev., 2006, 30(1), 1-23.
33. Wichmann, T.; Smith, Y.; Vitek, J. L. In: Basal ganglia: Anatomy and physiology, in Parkinson's disease diagnosis and clinical management, S. A. Factor and W. J. Weiner, Ed.; Demos Medical Publishing, LLC: New York, 2008; pp. 245-267.
34. Youdim, M. B. Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents? Exp. Neurobiol., 2010, 19(1), 1-14.
35. Nagatsu, T.; Sawada, M. L-dopa therapy for Parkinson's disease: Past, present, and future. Parkinsonism Relat. Disord., 2009, 15(Supplement 1), S3-S8.
36. Reis, J.; Encarnacao, I.; Gaspar, A.; Morales, A.; Milhazes, N.; Borges, F. Parkinson's disease management. part II discovery of MAO-B inhibitors based on nitrogen heterocycles and analogues. Curr. Top. Med. Chem., 2012, 12(20), 2116-2130.
37. Carlsson, A. The occurrence, distribution and physiological role of catecholamines in the nervous system. Pharmacol. Rev., 1959, 11(2, Part 2), 490-493.
38. Snyder, S. H. Virtuoso design of drugs. Nature, 1986, 323(6086), 292-293.
39. Uversky, V. In: α-Synuclein aggregation and Parkinson's disease, in protein misfolding, aggregation, and conformational diseases, V. Uversky and A. Fink, Ed.; Springer: US, 2007; pp. 61-110.
40. Malkus, K.; Tsika, E.; Ischiropoulos, H. Oxidative modifications, mitochondrial dysfunction, and impaired protein degradation in Parkinson's disease: How neurons are lost in the Bermuda triangle. Mol. Neurodegener., 2009, 4(1), 4-24.
41. Tansey, M. G.; McCoy, M. K.; Frank-Cannon, T. C. Neuroinflammatory mechanisms in Parkinson's disease: Potential environmental triggers, pathways, and targets for early therapeutic intervention. Exp. Neurol., 2007, 208(1), 1-25.
42. Fahn, S.; Cohen, G. The oxidant stress hypothesis in Parkinson's disease: Evidence supporting it. Ann. Neurol., 1992, 32(6), 804-812.
43. Hauser, D. N.; Hastings, T. G. Mitochondrial dysfunction and oxidative stress in Parkinson's disease and monogenic parkinsonism. Neurobiol. Dis., 2013, 51, 35-42.
44. Schapira, A. H.; Jenner, P. Etiology and pathogenesis of Parkinson's disease. Mov. Disord., 2011, 26(6), 1049-1055.
45. Youdim, M. B.; Maruyama, W.; Naoi, M. Neuropharmacological, neuroprotective and amyloid precursor processing properties of selective MAO-B inhibitor antiparkinsonian drug, rasagiline. Drugs Today, 2005, 41(6), 369-391.
46. Zheng, H.; Gal, S.; Weiner, L. M.; Bar-Am, O.; Warshawsky, A.; Fridkin, M.; Youdim, M. B. Novel multifunctional neuroprotective iron chelator-monoamine oxidase inhibitor drugs for neurodegenerative diseases: In vitro studies on antioxidant activity, prevention of lipid peroxide formation and monoamine oxidase inhibition. J. Neurochem., 2005, 95(1), 68-78.
47. Roger Kurlan, M. D. International symposium on early dopamine agonist therapy of Parkinson's disease. Arch. Neurol., 1988, 45(2), 204-208.
48. Schapira, A. H.; Olanow, C. W. Neuroprotection in Parkinson disease: Mysteries, myths, and misconceptions. JAMA, 2004, 291(3), 358-364.
49. Jenner, P. Preclinical evidence for neuroprotection with monoamine oxidase-B inhibitors in Parkinson's disease. Neurology, 2004, 63(7 suppl 2), S13-S22.
50. Takahata, K.; Shimazu, S.; Katsuki, H.; Yoneda, F.; Akaike, A. Effects of selegiline on antioxidant systems in the nigrostriatum in rat. J. Neural Transm., 2006, 113(2), 151-158.
51. Venugopala, K. N.; Rashmi, V.; Odhav, B. Review on natural coumarin lead compounds for their pharmacological activity. Biomed. Res. Int., 2013, 2013, 963248.
52. Harborne, J. B. The natural coumarins: Occurrence, chemistry and biochemistry. Plant Cell Environm., 1982, 5(6), 435-436.
53. Murray, R. D. H. In: Naturally occurring plant coumarins, in Progress in the Chemistry of Organic Natural Products, W. Herz Ed.; Springer: Vienna, 1991, pp. 83-316.
54. Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity. Curr. Med. Chem., 2005, 12(8), 887-916.
55. Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Simple coumarins: Privileged scaffolds in medicinal chemistry. Front. Med. Chem., 2009, 4, 23-85.
56. Daly, A. K. Optimal dosing of warfarin and other coumarin anticoagulants: The role of genetic polymorphisms. Arch. Toxicol., 2013, 87(3), 407-420.
57. Milatova, E.; Milata, V. Warfarin-its synthesis and properties in a twenty-year retrospective. Ceska Slov. Farm., 2013, 62(3), 111-119.
58. Vilar, S.; Quezada, E.; Santana, L.; Uriarte, E.; Yanez, M.; Fraiz, N.; Alcaide, C.; Cano, E.; Orallo, F. Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarinresveratrol hybrids. Bioorg. Med. Chem. Lett., 2006, 16(2), 257-261.
59. Amin, K. M.; Awadalla, F. M.; Eissa, A. A.; Abou-Seri, S. M.; Hassan, G. S. Design, synthesis and vasorelaxant evaluation of novel coumarin-pyrimidine hybrids. Bioorg. Med. Chem., 2011, 19(20), 6087-6097.
60. Pierson, J. T.; Dumetre, A.; Hutter, S.; Delmas, F.; Laget, M.; Finet, J. P.; Azas, N.; Combes, S. Synthesis and antiprotozoal activity of 4-arylcoumarins. Eur. J. Med. Chem., 2010, 45(3), 864-869.
61. Hwu, J. R.; Lin, S. Y.; Tsay, S. C.; De Clercq, E.; Leyssen, P.; Neyts, J. Coumarin-purine ribofuranoside conjugates as new agents against hepatitis C virus. J. Med. Chem., 2011, 54(7), 2114-2126.
62. Matos, M. J.; Vazquez-Rodriguez, S.; Santana, L.; Uriarte, E.; Fuentes-Edfuf, C.; Santos, Y.; Munoz-Crego, A. Looking for new targets: Simple coumarins as antibacterial agents. J. Med. Chem., 2012, 8(6), 1140-1145.
63. Sashidhara, K. V.; Avula, S. R.; Sharma, K.; Palnati, G. R.; Bathula, S. R. Discovery of coumarin-monastrol hybrid as potential antibreast tumor-specific agent. Eur. J. Med. Chem., 2013, 60, 120-127.
64. Bansal, Y.; Sethi, P.; Bansal, G. Coumarin: A potential nucleus for anti-inflammatory molecules. Med. Chem. Res., 2013, 22(7), 3049-3060.
65. Matos, M. J.; Hogger, V.; Gaspar, A.; Kachler, S.; Borges, F.; Uriarte, E.; Santana, L.; Klotz, KN. Synthesis and adenosine receptors binding affinities of a series of 3-arylcoumarins. J. Pharm. Pharmacol., 2013, 65(11), 1590-1597.
66. Matos, M. J.; Gaspar, A.; Kachler, S.; Klotz, K.-N.; Borges, F.; Santana, L.; Uriarte, E. Targeting adenosine receptors with coumarins: Synthesis and binding activities of amide and carbamate derivatives. J. Pharm. Pharmacol., 2013, 65(1), 30-34.
67. Anand, P.; Singh, B.; Singh, N. A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease. Bioorg. Med. Chem., 2012, 20(3), 1175-1180.
68. Matos, M. J.; Vina, D.; Vazquez-Rodriguez, S.; Uriarte, E.; Santana L. Focusing on new monoamine oxidase inhibitors: Differently substituted coumarins as an interesting scaffold. Curr. Top. Med. Chem., 2012, 12(20), 2210-2239.
69. da Silva, J. I.; de Moraes, M. C.; Vieira, L. C.; Correa, A. G.; Cass, Q. B.; Cardoso, C. L. Acetylcholinesterase capillary enzyme reactor for screening and characterization of selective inhibitors. J. Pharm. Biomed. Anal., 2013, 73, 44-52.
70. Patil, P. O.; Bari, S. B.; Firke, S. D.; Deshmukh, P. K.; Donda, S. T.; Patil, D. A. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease. Bioorg. Med. Chem., 2013, 21(9), 2434-2450.
71. Marumoto, S.; Miyazawa, M. Structure-activity relationships for naturally occurring coumarins as beta-secretase inhibitor. Bioorg. Med. Chem., 2012, 20(2), 784-788.
72. Mangialasche, F.; Solomon, A.; Winblad, B.; Mecocci, P.; Kivipelto, M. Alzheimer's disease: clinical trials and drug development. Lancet Neurol., 2010, 9(7), 702-716.
73. Asadipour, A.; Alipour, M.; Jafari, M.; Khoobi, M.; Emami, S.; Nadri, H.; Sakhteman, A.; Moradi, A.; Sheibani, V.; Homayouni Moghadam, F.; Shafiee, A.; Foroumadi, A. Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors. Eur. J. Med. Chem., 2013, 70, 623-630.
74. Zhou, X.; Wang, X. B.; Wang, T.; Kong, L. Y. Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues. Bioorg. Med. Chem., 2008, 16(17), 8011-8021.
75. Razavi, S. F.; Khoobi, M.; Nadri, H.; Sakhteman, A.; Moradi, A.; Emami, S.; Foroumadi, A.; Shafiee, A. Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors. Eur. J. Med. Chem., 2013, 64, 252-259.
76. Morphy, R.; Kay, C.; Rankovic, Z. From magic bullets to designed multiple ligands. Drug Discov. Today, 2004, 9(15), 641-651.
77. Garino, C.; Pietrancosta, N.; Laras, Y.; Moret, V.; Rolland, A.; Quelever, G.; Kraus, J. L. BACE-1 inhibitory activities of new substituted phenyl-piperazine coupled to various heterocycles: Chromene, coumarin and quinoline. Bioorg. Med. Chem. Lett., 2006, 16(7), 1995-1999.
78. Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F. Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: Biological activity and computational study. Bioorg. Med. Chem. Lett., 2004, 14(14), 3697-3703.
79. Secci, D.; Carradori, S.; Bolasco, A.; Chimenti, P.; Yanez, M.; Ortuso, F.; Alcaro, S. Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives. Eur. J. Med. Chem., 2011, 46(10), 4846-4852.
80. Pisani, L.; Muncipinto, G.; Miscioscia, T. F.; Nicolotti, O.; Leonetti, F.; Catto, M.; Caccia, C.; Salvati, P.; Soto-Otero, R.; Mendez-Alvarez, E.; Passeleu, C.; Carotti, A. Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: Development and biopharmacological profiling of 7-[(3-chlorobenzyl)oxy]-4-[(methylamino)methyl]-2H-chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor. J. Med. Chem., 2009, 52(21), 6685-6706.
81. Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Bizzarri, B.; Granese, A.; Carradori, S.; Yanez, M.; Orallo, F.; Ortuso, F.; Alcaro, S. Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins. J. Med. Chem., 2009, 52(7), 1935-1942.
82. Matos, M. J.; Vina, D.; Picciau, C.; Orallo, F.; Santana, L.; Uriarte, E. Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(17), 5053-5055.
83. Matos, M. J.; Vina, D.; Quezada, E.; Picciau, C.; Delogu, G.; Orallo, F.; Santana, L.; Uriarte, E. A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(12), 3268-3270.
84. Matos, M. J.; Vina, D.; Janeiro, P.; Borges, F.; Santana, L.; Uriarte, E. New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(17), 5157-5160.
85. Matos, M. J.; Vazquez-Rodriguez, S.; Uriarte, E.; Santana, L.; Vina, D. MAO inhibitory activity modulation: 3-Phenylcoumarins versus 3-benzoylcoumarins. Bioorg. Med. Chem. Lett., 2011, 21(14), 4224-4227.
86. Matos, M. J.; Teran, C.; Perez-Castillo, Y.; Uriarte, E.; Santana, L.; Vina, D. Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors. J. Med. Chem., 2011, 54(20), 7127-7137.
87. Serra, S.; Ferino, G.; Matos, M. J.; Vazquez-Rodriguez, S.; Delogu, G.; Vina, D.; Cadoni, E.; Santana, L.; Uriarte, E. Hydroxycoumarins as selective MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2012, 22(1), 258-261.
88. Santana, L.; Gonzalez-Diaz, H.; Quezada, E.; Uriarte, E.; Yanez, M.; Vina, D.; Orallo, F. Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. J. Med. Chem., 2008, 51(21), 6740-6751.
89. Min Kyun, N.; Phuong Thien, T.; Ki Hwan, B. Natural compounds with antioxidant activity: Recent findings from studies on medicinal plants. Nat. Prod. Sci., 2011, 17(2), 65-79.
90. Grosso, C.; Valentao, P.; Ferreres, F.; Andrade, P. B. The use of flavonoids in central nervous system disorders. Curr. Med. Chem., 2013, 20(37), 4694-4719.
91. Bubols, G. B.; Vianna, D. R.; Medina-Remon, A.; von Poser, G.; Lamuela-Raventos, R. M., Eifler-Lima, V. L.; Garcia, S. C. The antioxidant activity of coumarins and flavonoids. Mini Rev. Med. Chem., 2013, 13(3), 318-334.
92. Aboul-Enein, H. Y.; Berczynsk, P.; Kruk, I. Phenolic compounds: the role of redox regulation in neurodegenerative disease and cancer. Mini Rev. Med. Chem., 2013, 13(3), 385-398.
93. Mohammadi, M.; Yousefi, M.; Habibi, Z.; Shafiee, A. Two new coumarins from the chloroform extract of Angelica urumiensis from Iran. Chem. Pharm. Bull., 2010, 58(4), 546-548.
94. Beillerot, A.; Dominguez, J. C.; Kirsch, G.; Bagrel, D. Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin. Bioorg. Med. Chem. Lett., 2008, 18(3), 1102-1105.
95. Zhu, Y.; Zhang, L.-X.; Zhao, Y.; Huang, G.-D. Unusual sesquiterpene lactones with a new carbon skeleton and new acetylenes from Ajania przewalskii. Food Chem., 2010, 118(2), 228-238.
96. Thuong, P. T.; Hung, T. M.; Ngoc, T. M.; Ha do, T.; Min, B. S.; Kwack, S. J.; Kang, T. S.; Choi, J. S.; Bae, K. Antioxidant activities of coumarins from Korean medicinal plants and their structureactivity relationships. Phytother. Res., 2010, 24(1), 101-106.
97. Guinez, R. F.; Matos, M. J.; Vazquez-Rodriguez, S.; Santana, L.; Uriarte, E.; Olea-Azar, C.; Maya, J. D. Synthesis and evaluation of antioxidant and trypanocidal properties of a selected series of coumarin derivatives. Fut. Med. Chem., 2013, 5(16), 1911-1922.
98. Kostova, I. Synthetic and natural coumarins as antioxidants. Mini Rev. Med. Chem., 2006, 6(4), 365-374.
99. Yordi, E. G.; Molina, E.; Matos, M. J.; Uriarte, E. In: Nutrition, well-being and health; D. J. B., Ed.; InTech: Croatia, 2012; pp. 23-48.
100. Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Detsi, A.; Koufaki, M.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur. J. Med. Chem., 2009, 44(7), 3020-3026.
101. Morabito, G.; Trombetta, D.; Singh Brajendra, K.; Prasad Ashok, K.; Parmar Virinder, S.; Naccari, C.; Mancari, F.; Saija, A.; Cristani, M.; Firuzi, O.; Saso, L. Antioxidant properties of 4-methylcoumarins in in vitro cell-free systems. Biochimie, 2010, 92(9), 1101-1107.
102. Gacche, R. N.; Jadhav, S. G. Antioxidant activities and cytotoxicity of selected coumarin derivatives: Preliminary results of a structure-activity relationship study using computational tools. J. Exp. Clin. Med., 2012, 4(3), 165-169.
103. Lin, M.-H.; Chou, Y.-S.; Tsai, Y.-J.; Chou, D.-S. Antioxidant properties of 5, 7-dihydroxycoumarin derivatives in in vitro cellfree and cell-containing systems. J. Exp. Clin. Med., 2011, 3(3), 126-131.
104. Calil, N. O.; Senra Goncalves de Carvalho, G.; Farah da Silva, A.; da Silva, A. D.; Rezende Barbosa Raposo, N. Antioxidant activity of synthetic resveratrol analogs: A structure-activity insight. Lett. Drug Des. Discov., 2012, 9(7), 676-679.
105. He, S.; Yan, X. From resveratrol to its derivatives: New sources of natural antioxidant. Curr. Med. Chem., 2013, 20(8), 1005-1017.
106. Kumar, A.; Negi, G.; Sharma, S. S. Neuroprotection by resveratrol in diabetic neuropathy: Concepts & mechanisms. Curr. Med. Chem., 2013, 20(36), 4640-4645.
107. Garcia, G. X.; Larsen, S. W.; Pye, C.; Galbreath, M.; Isovitsch, R.; Fradinger, E. A. The functional group on (E)-4, 4'-disubstituted stilbenes influences toxicity and antioxidative activity in differentiated PC-12 cells. Bioorg. Med. Chem. Lett., 2013, 23, 6355-6359.
108. Hamdi, N.; Bouabdallaha, F.; Romerosab, A.; Benhassenc, R. Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents. Comptes Rendus Chimie, 2010, 13(10), 1261-1268.
109. Hamdi, N.; Fischmeister, C.; Puerta, M. C.; Valerga, P. A rapid access to new coumarinyl chalcone and substituted chromeno[4, 3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities. Med. Chem. Res., 2011, 20(4), 522-530.
110. Balabani, A.; Hadjipavlou-Litina, D. J.; Litinas, K. E.; Mainou, M.; Tsironi, C. C.; Vronteli, A. Synthesis and biological evaluation of (2, 5-dihydro-1H-pyrrol-1-yl)-2H-chromen-2-ones as free radical scavengers. Eur. J. Med. Chem., 2011, 46(12), 5894-5901.
111. Kadhum, A. A.; Al-Amiery, A. A.; Musa, A. Y.; Mohamad, A. B. The antioxidant activity of new coumarin derivatives. Int. J. Mol. Sci., 2011, 12(9), 5747-5761.
112. Manojkumar, P.; Ravi, T. K.; Gopalakrishnan, S. Antioxidant and antibacterial studies of arylazopyrazoles and arylhydrazonopyrazolones containing coumarin moiety. Eur. J. Med. Chem., 2009, 44(11), 4690-4694.
113. Gouda, M. A.; Berghot, M. A.; Baz, E. A.; Hamama, W. S. Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety. Med. Chem. Res., 2012, 21(7), 1062-1070.
114. Panteleon, V.; Kostakis, I. K.; Marakos, P.; Pouli, N.; Andreadou, I. Synthesis and free radical scavenging activity of some new spiropyranocoumarins. Bioorg. Med. Chem. Lett., 2008, 18(21), 5781-5784.
115. Symeonidis, T.; Chamilos, M.; Hadjipavlou-Litina, D. J.; Kallitsakis, M.; Litinas, K. E. Synthesis of hydroxycoumarins and hydroxybenzo[ f]-or [h]coumarins as lipid peroxidation inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(4), 1139-1142.
116. Nealmongkol, P.; Tangdenpaisal, K.; Sitthimonchai, S.; Ruchirawata, S.; Thasana, N. Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A-C. Tetrahedron, 2013, 69(44), 9277-9283.
117. Khoobi, M.; Foroumadi, A.; Emami, S.; Safavi, M.; Dehghan, G.; Alizadeh, B. H.; Ramazani, A.; Ardestani, S. K.; Shafiee, A. Coumarin-based bioactive compounds: facile synthesis and biological evaluation of coumarin-fused 1, 4-thiazepines. Chem. Biol. Drug Des., 2011, 78(4), 580-586.
118. Sri Ranganath, Y.; Harinadha Babu, V.; Sandeep, G.; Parameshwar, R. Synthesis and evaluation of some novel furocoumarin de rivatives for radical scavenging profile and cytotoxic studies. J. Chem. Pharm. Res., 2011, 3(4), 62-68.
119. Hertel, C.; Terzi, E.; Hauser, N.; Jakob-Rotne, R.; Seelig, J.; Kemp, J. A. Inhibition of the electrostatic interaction between β-amyloid peptide and membranes prevents β-amyloid-induced toxicity. Proc. Natl. Acad. Sci. U. S. A., 1997, 94(17), 9412-9416.
120. Mogana, R.; Teng-Jin, K.; Wiart, C. Anti-inflammatory, anticholinesterase, and antioxidant potential of scopoletin isolated from Canarium patentinervium Miq. (Burseraceae Kunth). Evid. Based Complement Alternat. Med., 2013, 2013, 734824.
121. Kontogiorgis, C. A.; Xu, Y.; Hadjipavlou-Litina, D.; Luo, Y. Coumarin derivatives protection against ROS production in cellular models of Abeta toxicities. Free Radic. Res., 2007, 41(10), 1168-1180.
122. Janeiro, P.; Matos, M. J.; Santana, L.; Uriarte, E.; Oliveira-Brett, A. M. New hydroxylated 3-arylcoumarins, synthesis and electrochemical study. J. Electroanal. Chem., 2013, 689, 243-251.
123. Perez-Cruz, F.; Vazquez-Rodriguez, S.; Matos, M. J.; Herrera-Morales, A.; Villamena, F. A.; Das, A.; Gopalakrishnan, B.; Olea-Azar, C.; Santana, L.; Uriarte, E. Synthesis and electrochemical and biological studies of novel coumarin-chalcone hybrid compounds. J. Med. Chem., 2013, 56(15), 6136-6145.
124. Fylaktakidou, K. C.; Hadjipavlou-Litina, D. J.; Litinas, K. E.; Nicolaides, D. N. Natural and synthetic coumarin derivatives with antiinflammatory/antioxidant activities. Curr. Pharm. Des., 2004, 10(30), 3813-3833.
125. Bandgar, B. P.; Jalde, S. S.; Adsul, L. K.; Shringare, S. N.; Lonikar, S. V.; Gacche, R. N.; Dhole, N. A.; Nile, S. H.; Shirfule, A. L. Synthesis of new olefin chalcone derivatives as antitumor, antioxidant and antimicrobial agents. Med. Chem. Res., 2012, 21(12), 4512-4522.
126. Shenvi, S.; Kumar, K.; Hatti, K. S.; Rijesh, K.; Diwakar, L.; Reddy, G. C. Synthesis, anticancer and antioxidant activities of 2, 4, 5-trimethoxy chalcones and analogues from asaronaldehyde: structure-activity relationship. Eur. J. Med. Chem., 2013, 62, 435-442.
127. Vazquez-Rodriguez, S.; Figueroa-Guinez, R.; Matos, M. J.; Santana, L.; Uriarte, E.; Lapier, M.; Maya, J. D.; Olea-Azar, C. Synthesis of coumarin-chalcone hybrids and evaluation of their antioxidant and trypanocidal properties. MedChemComm, 2013, 4(6), 993-1000.
128. Gilbert, E. R.; Liu, D. Flavonoids influence epigenetic-modifying enzyme activity: Structure-function relationships and the therapeutic potential for cancer. Curr. Med. Chem., 2010, 17, 1756-1768.
129. Veitch, N. C.; Grayer, R. J. Flavonoids and their glycosides, including anthocyanins. Nat. Prod. Rep., 2011, 28(10), 1626-1695.
130. Oyama, K.-I.; Yoshida, K.; Kondo, T. Recent progress in the synthesis of flavonoids: From monomers to supra-complex molecules. Curr. Org. Chem., 2011, 15(15), 2567-2607.
131. Jacob, V.; Hagai, T.; Soliman, K. Structure-activity relationships of flavonoids. Curr. Org. Chem., 2011, 15(15), 2641-2657.
132. Corradini, E.; Foglia, P.; Giansanti, P.; Gubbiotti, R.; Samperi, R.; Lagana, A. Flavonoids: chemical properties and analytical methodologies of identification and quantitation in foods and plants. Nat. Prod. Res., 2011, 25(5), 469-495.
133. Jones, Q. R. D.; Warford, J.; Rupasinghe, H. P.; Robertson, G. S. Target-based selection of flavonoids for neurodegenerative disorders. Trends Pharmacol. Sci., 2012, 33(11), 602-610.
134. Ramassamy, C. Emerging role of polyphenolic compounds in the treatment of neurodegenerative diseases: a review of their intracellular targets. Eur. J. Pharmacol., 2006, 545(1), 51-64.
135. Romano, B.; Pagano, E.; Montanaro, V.; Fortunato, A. L.; Milic, N.; Borrelli, F. Novel insights into the pharmacology of flavonoids. Phytother. Res., 2013, 27(11), 1588-1596.
136. Malar, D. S.; Devi, K. P. Dietary polyphenols for treatment of Alzheimer's disease-future research and development. Curr. Pharm. Biotechnol., 2014, 15(4), 330-342.
137. Lee, J.-H.; Kim, G.-H. Evaluation of antioxidant and inhibitory activities for different subclasses flavonoids on enzymes for rheumatoid arthritis. J. Food Sci., 2010, 75(7), H212-H217.
138. Yan, J.; Zhang, G.; Hu, Y.; Ma, Y. Effect of luteolin on xanthine oxidase: Inhibition kinetics and interaction mechanism merging with docking simulation. Food Chem., 2013, 141(4), 3766-3773.
139. Chimenti, F.; Fioravanti, R.; Bolasco, A.; Chimenti, P.; Secci, D.; Rossi, F.; Yanez, M.; Orallo, F.; Ortuso, F.; Alcaro, S.; Cirilli, R.; Ferretti, R.; Sanna, M. L. A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors. Bioorg. Med. Chem., 2010, 18(3), 1273-1279.
140. Singh, M.; Kaur, M.; Silakari, O. Flavones: An important scaffold for medicinal chemistry. Eur. J. Med. Chem., 2014, 84, 206-239.
141. Baptista, F. I.; Henriques, A. G.; Silva, A. M.; Wiltfang, J.; da Cruz e Silva, O. A. Flavonoids as therapeutic compounds targeting key proteins involved in Alzheimer's disease. ACS Chem. Neurosci., 2014, 5(2), 83-92.
142. Kumazawa, Y., Takimoto, H.; Matsumoto, T.; Kawaguchi, K. Potential use of dietary natural products, especially polyphenols, for improving type-1 allergic symptoms. Curr. Pharm. Des., 2014, 20(6), 857-863.
143. Spencer, J. P. E., The impact of fruit flavonoids on memory and cognition. Br. J. Nutr., 2010, 104(3), S40-S47.
144. Mladěnka, P.; Zatloukalova, L.; Filipsky, T.; Hrdina, R. Cardiovascular effects of flavonoids are not caused only by direct antioxidant activity. Free Radic. Biol. Med., 2010, 49(6), 963-975.
145. Bennett, L. L.; Seefeldt, T. The role of antioxidants on oxidative stress in diabetes mellitus. J. Pharm. Technol., 2010, 26(5), 293-299.
146. Nones, J.; Stipursky, J.; Costa, S. L.; Gomes, F. C. Flavonoids and astrocytes crosstalking: Implications for brain development and pathology. Neurochem. Res., 2010, 35(7), 955-966.
147. Lee, M.; Hyun, D. H.; Marshall, K. A.; Ellerby, L. M.; Bredesen, D. E.; Jenner, P.; Halliwell, B. Effect of overexpression of BCL-2 on cellular oxidative damage, nitric oxide production, antioxidant defenses, and the proteasome. Free Radic. Biol. Med., 2001, 31(12), 1550-1559.
148. Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chromone: A valid scaffold in medicinal chemistry. Chem. Rev., 2014, 114(9), 4960-4992.
149. Heo, H. J.; Lee, C. Y. Protective effects of quercetin and vitamin C against oxidative stress-induced neurodegeneration. J. Agric. Food Chem., 2004, 52(25), 7514-7517.
150. Dajas, F.; Arredondo, F.; Echeverry, C.; Ferreira, M.; Morquio, A.; Rivera, F. Flavonoids and the brain: Evidences and putative mechanisms for a protective capacity. Curr. Neuropharmacol., 2005, 3(3), 193-205.
151. Ossola, B., Kaariainen, T. M.; Mannisto, P. T. The multiple faces of quercetin in neuroprotection. Expert Opin. Drug Saf., 2009, 8(4), 397-409.
152. Jakubowicz-Gil, J.; Rzeski, W.; Zdzisinska, B.; Dobrowolski, P.; Gawron, A. Cell death and neuronal arborization upon quercetin treatment in rat neurons. Acta Neurobiol. Exp., 2008, 68(2), 139-146.
153. Zbarsky, V.; Datla, K. P.; Parkar, S.; Rai, D. K.; Aruoma, O. I.; Dexter, D. T. Neuroprotective properties of the natural phenolic antioxidants curcumin and naringenin but not quercetin and fisetin in a 6-OHDA model of Parkinson's disease. Free Radic. Res., 2005, 39(10), 1119-1125.
154. Haleagrahara, N.; Siew, C. J.; Mitra, N. K.; Kumari, M. Neuroprotective effect of bioflavonoid quercetin in 6-hydroxydopamineinduced oxidative stress biomarkers in the rat striatum. Neurosci. Lett., 2011, 500(2), 139-143.
155. Choi, Y. T.; Jung, C. H.; Lee, S. R.; Bae, J. H.; Baek, W. K.; Suh, M. H.; Park, J.; Park, C. W.; Suh, S. I. The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons. Life Sci., 2001, 70(5), 603-614.
156. Mandel, S.; Amit, T.; Reznichenko, L.; Weinreb, O.; Youdim, M. B. Green tea catechins as brain-permeable, natural iron chelators-antioxidants for the treatment of neurodegenerative disorders. Mol. Nutr. Food Res., 2006, 50(2), 229-234.
157. Andersen, J. M.; Myhre, O.; Fonnum, F. Discussion of the role of the extracellular signal-regulated kinase-phospholipase A2 pathway in production of reactive oxygen species in Alzheimer's disease. Neurochem. Res., 2003, 28(2), 319-326.
158. Lee, M.-H.; Lin, R. D.; Shen, L. Y.; Yang, L. L.; Yen, K. Y.; Hou, W. C. Monoamine oxidase B and free radical scavenging activities of natural flavonoids in melastoma candidum D. Don. J. Agric. Food Chem., 2001, 49(11), 5551-5555.
159. Desideri, N.; Bolasco, A.; Fioravanti, R.; Monaco, L. P.; Orallo, F.; Yanez, M.; Ortuso, F.; Alcaro, S. Homoisoflavonoids: Natural scaffolds with potent and selective monoamine oxidase-B inhibition properties. J. Med. Chem., 2011, 54(7), 2155-2164.
160. Alcaro, S.; Gaspar, A.; Ortuso, F.; Milhazes, N.; Orallo, F.; Uriarte, E.; Yanez, M.; Borges, F. Chromone-2-and-3-carboxylic acids in hibit differently monoamine oxidases A and B. Bioorg. Med. Chem. Lett., 2010, 20(9), 2709-2712.
161. Gaspar, A.; Silva, T.; Yanez, M.; Vina, D.; Orallo, F.; Ortuso, F.; Uriarte, E.; Alcaro, S.; Borges, F. Chromone, a privileged scaffold for the development of monoamine oxidase inhibitors. J. Med. Chem., 2011, 54(14), 5165-5173.
162. Gaspar, A.; Reis, J.; Fonseca, A.; Milhazes, N.; Vina, D.; Uriarte, E.; Borges, F. Chromone 3-phenylcarboxamides as potent and selective MAO-B inhibitors. Bioorg. Med. Chem. Lett., 2011, 21(2), 707-709.
163. Legoabe, L. J.; Petzer, A.; Petzer, J. P. Selected chromone derivatives as inhibitors of monoamine oxidase. Bioorg. Med. Chem. Lett., 2012, 22(17), 5480-5484.
164. Legoabe, L. J.; Petzer, A.; Petzer, J. P. Selected C7-substituted chromone derivatives as monoamine oxidase inhibitors. Bioorg. Chem., 2012, 45, 1-11.
165. Legoabe, L. J.; Petzer, A.; Petzer, J. P. Inhibition of monoamine oxidase by selected C6-substituted chromone derivatives. Eur. J. Med. Chem., 2012, 49, 343-353.
166. Bruhlmann, C.; Ooms, F.; Carrupt, P. A.; Testa, B.; Catto, M.; Leonetti, F.; Altomare, C.; Carotti, A. Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase. J. Med. Chem., 2001, 44(19), 3195-3198.
167. Fernandez-Bachiller, M. I.; Perez, C.; Gonzalez-Munoz, G. C.; Conde, S.; Lopez, M. G.; Villarroya, M.; Garcia, A. G.; Rodriguez-Franco, M. I. Novel tacrine-8-hydroxyquinoline hybrids as multifunctional agents for the treatment of Alzheimer's disease, with neuroprotective, cholinergic, antioxidant, and copper-complexing properties. J. Med. Chem., 2010, 53(13), 4927-4937.
168. Fernandez-Bachiller, M. I.; Perez, C.; Monjas, L.; Rademann, J.; Rodriguez-Franco, M. I. New tacrine-4-oxo-4H-chromene hybrids as multifunctional agents for the treatment of Alzheimer's disease, with cholinergic, antioxidant, and beta-amyloid-reducing properties. J. Med. Chem., 2012, 55(3), 1303-1317.
169. Gilgun-Sherki, Y.; Melamed, E.; Offen, D. Oxidative stress induced-neurodegenerative diseases: The need for antioxidants that penetrate the blood brain barrier. Neuropharmacol., 2001, 40(8), 959-975.
170. Spencer, J. P. E. Flavonoids: Modulators of brain function? Br. J. Nutr., 2008, 99 (1), ES60-77.
171. Kuroda, M.; Uchida, S.; Watanabe, K.; Mimaki, Y. Chromones from the tubers of Eranthis cilicica and their antioxidant activity. Phytochemistry, 2009, 70(2), 288-293.
172. Asamenew, G.; Bisrat, D.; Mazumder, A.; Asres, K. In Vitro Antimicrobial and antioxidant activities of anthrone and chromone from the latex of Aloe harlana Reynolds. Phytother. Res., 2011, 25(12), 1756-1760.
173. Kuo, L. M. Y.; Zhang, L. J.; Huang, H. T.; Lin, Z. H.; Liaw, C. C.; Cheng, H. L.; Lee, K. H.; Morris-Natschke, S. L.; Kuo, Y. H.; Ho, H. O. Antioxidant lignans and chromone glycosides from Eurya japonica. J. Nat. Prod., 2013, 76(4), 580-587.
174. Mohamed, Y. M. A.; Vik, A.; Hofer, T.; Andersen, J. H.; Hansen, T. V. Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity. Chem. Phys. Lipids, 2013, 170-1717, 41-45.
175. Berczyński, P.; Kładna, A.; Kruk, I.; Piechowska, T.; Aboul-Enein, H. Y.; Bozdağ-Dundar, O.; Ceylan-Unlusoy, M. Antioxidant activities of some new chromonyl-2, 4-thiazolidinediones and chromonyl-2, 4-imidazolidinediones having chromone cores. J. Fluoresc., 2013, 23(6), 1319-1327.
176. Kładna, A.; Berczyński, P.; Piechowska, T.; Kruk, I.; Aboul-Enein, H. Y.; Ceylan-Unlusoy, M.; Verspohl, E. J.; Ertan, R. Studies on the antioxidant activities of some new chromone compounds. Luminescence, 2014, 29(7), 846-853.
177. Kim, S. H.; Lee, Y. H.; Jung, S. Y.; Kim, H. J.; Jin, C.; Lee, Y. S. Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties. Eur. J. Med. Chem., 2011, 46(5), 1721-1728.
178. Fernandes, E.; Carvalho, F.; Silva, A. M.; Santos, C. M.; Pinto, D. C.; Cavaleiro, J. A. Bastos, M. L. 2-Styrylchromones as novel inhibitors of xanthine oxidase. A structure-activity study. J. Enzyme Inhib. Med. Chem., 2002, 17(1), 45-48.
179. Fernandes, E.; Carvalho, M.; Carvalho, F.; Silva, A. M.; Santos, C. M.; Pinto, D. C.; Cavaleiro, J. A.; Bastos, M. L. Hepatoprotective activity of polyhydroxylated 2-styrylchromones against tertbutylhydroperoxide induced toxicity in freshly isolated rat hepatocytes. Arch. Toxicol., 2003, 77(9), 500-505.
180. Filipe, P.; Silva, A. M.; Morliere, P.; Brito, C. M.; Patterson, L. K.; Hug, G. L.; Silva, J. N.; Cavaleiro, J. A.; Maziere, J. C.; Freitas, J. P.; Santus, R. Polyhydroxylated 2-styrylchromones as potent antioxidants. Biochem. Pharmacol., 2004, 67(12), 2207-2218.
181. Gomes, A.; Fernandes, E.; Silva, A. M.; Santos, C. M.; Pinto, D. C.; Cavaleiro, J. A.; Lima, J. L. 2-Styrylchromones: Novel strong scavengers of reactive oxygen and nitrogen species. Bioorg. Med. Chem., 2007, 15(18), 6027-6036.
182. Gomes, A.; Neuwirth, O.; Freitas, M.; Couto, D.; Ribeiro, D.; Figueiredo, A. G.; Silva, A. M.; Seixas, R. S.; Pinto, D. C.; Tome, A. C.; Cavaleiro, J. A.; Fernandes, E.; Lima, J. L. Synthesis and antioxidant properties of new chromone derivatives. Bioorg. Med. Chem., 2009, 17(20), 7218-7226.
183. Gomes, A.; Freitas, M.; Fernandes, E.; Lima, J. L. Biological activities of 2-styrylchromones. Mini Rev. Med. Chem., 2010, 10(1), 1-7.
184. Pawar, S.; Kondhare, D.; Zubaidha, P. K. Synthesis and evaluation of antioxidant activity of 2-styrylchromones. Med. Chem. Res., 2013, 22(2), 753-757.
185. Wang, J.; Yang, Z. Y.; Wang, B. D.; Yi, X. Y.; Liu, Y. C. Synthesis, characterization and DNA-binding properties of Ln(III) complexes with 6-ethoxy chromone-3-carbaldehyde benzoyl hydrazone. J. Fluoresc., 2009, 19(5), 847-856.
186. Li, Y.; Yang, Z. Y. DNA-binding properties and antioxidant activity of lanthanide complexes with the Schiff base derived from 3-carbaldehyde chromone and isonicotinyl hydrazine. J. Coord. Chem., 2010, 63(11), 1960-1968.
187. Li, Y.; Yang, Z.-Y. Rare earth complexes with 3-carbaldehyde chromone-(benzoyl) hydrazone: Synthesis, characterization, DNA binding studies and antioxidant activity. J. Fluoresc., 2010, 20(1), 329-342.
188. Grażul, M.; Kufelnicki, A.; Wozniczka, M.; Lorenz, I.-P.; Mayer, P.; Joz wiak, A.; Czy, M.; Budzis, E. Synthesis, structure, electrochemical properties, cytotoxic effects and antioxidant activity of 5-amino-8-methyl-4H-benzopyran-4-one and its copper(II) complexes. Polyhedron, 2012, 31(1), 150-158.
189. Kowalski, K.; Hikisz, P.; Szczupak, Ł.; Therrien, B.; Koceva-Chyła, A. Ferrocenyl and dicobalt hexacarbonyl chromones-New organometallics inducing oxidative stress and arresting human cancer cells in G2/M phase. Eur. J. Med. Chem., 2014, 81, 289-300.