Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA

Medicinal Chemistry Research

Volumn 22, Issue 4, 2013, Pages 1563-1569

  Wang, Rui ^a   Liu, Zai Qun ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

Antioxidant; Free radical; Furoquinoline; Oxidation of DNA

Indexed keywords

4 METHYL 2,3 DIHYDROFURO[2,3 B ]QUINOLIN 6 OL; 4 METHYL 2,3 DIHYDROFURO[2,3 B ]QUINOLIN 7 OL; 4 METHYL 2,3 DIHYDROFURO[2,3 B ]QUINOLIN 8 OL; ANTIOXIDANT; DNA; FUROQUINOLINE; GLUTATHIONE; HYDROGEN; HYDROXYL GROUP; OXYGEN; QUINOLINE DERIVATIVE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; ATOM; DRUG SYNTHESIS; OXIDATION; STOICHIOMETRY;

EID: 84879691253     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0157-0     Document Type: Article

References (30)

1. Battin EE, Brumaghim JL (2008) Metal specificity in DNA damage prevention by sulfur antioxidants. J Inorg Biochem 102:2036-2042
2. Benigni R, Bossa C (2011) Mechanisms of chemical carcinogenicity and mutagenicity: a review with implications for predictive toxicology. Chem Rev 111:2507-2536
3. Bowry VW, Stocker R (1993) Tocopherol-mediated peroxidation: the prooxidation effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. J Am Chem Soc 115:6029-6044
4. Chang G-J, Lin T-P, Ko Y-S et al (2010) Endothelium-dependent and -independent vasorelaxation induced by CIJ-3-2F, a novel benzyl-furoquinoline with antiarrhythmic action, in rat aorta. Life Sci 86:869-879
5. Chen Y-L, Chen I-L, Lu C-M et al (2004) Synthesis and anti-inflammatory evaluation of 4-anilinofuro[2,3-b]quinoline and 4-phenoxyfuro[2,3-b]quinoline derivatives. Part 3. Bioorg Med Chem 12:387-392
6. Dedon PC (2008) The chemical toxicology of 2-deoxyribose oxidation in DNA. Chem Res Toxicol 21:206-219
7. Fayol A, Zhu J (2002) Synthesis of furoquinolines by a multicomponent domino process. Angew Chem Int Ed 41:3633-3635
8. Feng J-Y, Liu Z-Q (2011) Feruloylacetone as the model compound of half-curcumin: synthesis and antioxidant properties. Eur J Med Chem 46:1198-1206
9. Galano A, Macías-Ruvalcaba NA, Campos ONM et al (2010) Mechanism of the OH radical scavenging activity of nordihydroguaiaretic acid: a combined theoretical and experimental study. J Phys Chem B 114:6625-6635
10. Halliwell B (2009) The wanderings of a free radical. Free Radical Biol Med 46:531-542
11. Hu J-F, Fan H, Xiong J et al (2011) Discorhabdins and pyrroloiminoquinone-related alkaloids. Chem Rev 111:5465-5491
12. Leopoldini M, Russo N, Toscano M (2011) The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem 125:288-306
13. Li G-X, Liu Z-Q, Luo X-Y (2010a) Dichloro-4-quinolinol-3-carboxylic acid: synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA. Eur J Med Chem 45:1821-1827
14. Li Y-F, Liu Z-Q, Luo X-Y (2010b) Properties of synthetic homoisoflavonoids to reduce oxidants and to protect linoleic acid and DNA against oxidations. J Agric Food Chem 58:4126-4131
15. Liu Z-C, Wang B-D, Yang Z-Y et al (2009) Synthesis, crystal structure, DNA interaction and antioxidant activities of two novel water-soluble Cu(2+) complexes derivated from 2-oxo-quinoline-3-carbaldehyde Schiff-bases. Eur J Med Chem 44:4477-4484
16. Mena S, Ortega A, Estrela JM (2009) Oxidative stress in environmental-induced carcinogenesis. Mutat Res 674:36-44
17. Michael JP (2008) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 25:166-187
18. Niki E (2010) Assessment of antioxidant capacity in vitro and in vivo. Free Radic Biol Med 49:503-515
19. Ohta Y, Shiraishi N, Nishikawa T et al (2000) Copper-catalyzed autoxidations of GSH and L-ascorbic acid: mutual inhibition of the respective oxidations by their coexistence. Biochim Biophys Acta 1474:378-382
20. Reed CJ, Douglas KT (1991) Chemical cleavage of plasmid DNA by glutathione in the presence of Cu(II) ions. The Cu(II)-thiol system for DNA strand scission. Biochem J 275:601-608
21. Shao J, Geacintov NE, Shafirovich V (2010) Oxidative modification of guanine bases initiated by oxyl radicals derived from photolysis of azo compounds. J Phys Chem B 114:6685-6692
22. van Horssen J, Witte ME, Schreibelt G et al (2011) Radical changes in multiple sclerosis pathogenesis. Biochim Biophys Acta 1812:141-150
23. Wansi JD, Mesaik MA, Chiozem DD et al (2008) Oxidative burst inhibitory and cytotoxic indoloquinazoline and furoquinoline alkaloids from Oricia suaveolens. J Nat Prod 71:1942-1945
24. Wansi JD, Hussain H, Tcho AT et al (2010) Antiplasmodial activities of furoquinoline alkaloids from Teclea afzelii. Phytother Res 24:775-777
25. Yang C-L, Tseng C-H, Chen Y-L et al (2010) Identification of benzofuro[2,3-b]quinoline derivatives as a new class of antituberculosis agents. Eur J Med Chem 45:602-607
26. Zennaro L, Rossetto M, Vanzani P et al (2007) A method to evaluate capacity and efficiency of water soluble antioxidants as peroxyl radical scavengers. Arch Biochem Biophys 462:38-46
27. Zhang Z, Zhang Q, Sun S et al (2007) Domino ring-opening/recyclization reactions of doubly activated cyclopropanes as a strategy for the synthesis of furoquinoline derivatives. Angew Chem Int Ed 46:1726-1729
28. Zhao F, Liu Z-Q (2009) The protective effect of hydroxyl-substituted Schiff bases on the radical-induced oxidation of DNA. J Phys Org Chem 22:791-798
29. Zhao F, Zhao C, Liu Z-Q (2011) Synthesis of hydroxyferrocifen and its abilities to protect DNA and to scavenge radicals. J Biol Inorg Chem 16:1169-1176
30. Zhu BZ, Kitrossky N, Chevion M (2000) Evidence for production of hydroxyl radicals by pentachlorophenol metabolites and hydrogen peroxide: a metal-independent organic Fenton reaction. Biochem Biophys Res Commun 270:942-946