Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase

References

• Solomon EI, Zhou J, Neese F, Pavel EG. New insights from spectroscopy into the structure/function relationships of lipoxygenases. Chem Biol 1997;4:795–808
   PubMed Web of Science ®Google Scholar
• Kuhn H, Thiele BJ. The diversity of the lipoxygenase family. Many sequence data but little information on biological significance. FEBS Lett 1999;449:7–11
   PubMed Web of Science ®Google Scholar
• Serhan CN, Petasis NA. Resolvins and protectins in inflammation resolution. Chem Rev 2011;111:5922–43
   PubMed Web of Science ®Google Scholar
• Kashfi K. Anti-inflammatory agents as cancer therapeutics. In: Enna SJ, Williams M, eds. Contemporary aspects of biomedical research: drug discovery. Amsterdam: Academic Press; 2009:31–56
   Google Scholar
• Pratico D, Zhukareva V, Yao Y, et al 12/15-Lipoxygenase is increased in Alzheimer’s disease: possible involvement in brain oxidative stress. Am J Pathol 2004;164:1655–62
   PubMed Web of Science ®Google Scholar
• Cyrus T, Witztum JL, Rader DJ, et al Disruption of the 12/15-lipoxygenase gene diminishes atherosclerosis in apo E-deficient mice. J Clin Invest 1999;103:1597–604
   PubMed Web of Science ®Google Scholar
• Harats D, Shaish A, George J, et al Overexpression of 15-lipoxygenase in vascular endothelium accelerates early atherosclerosis in LDL receptor-deficient mice. Arteriosler Thromb Vasc Biol 2000;20:2100–5
   PubMed Web of Science ®Google Scholar
• Kuhn H, Walther M, Kuban RJ. Mammalian arachidonate 15-lipoxygenases: structure, function, and biological implications. Prostaglandins Other Lipid Mediat 2002;68–69:263–90
   PubMed Web of Science ®Google Scholar
• Gundersen LL, Malterud KE, Negussie AH, et al Indolizines as novel potent inhibitors of 15-lipoxygenase. Bioorg Med Chem 2003;11:5409–15
   PubMed Web of Science ®Google Scholar
• Teklu S, Gundersen LL, Larsen T, et al Indolizine 1-sulfonates as potent inhibitors of 15-lipoxygenase from soybeans. Bioorg Med Chem 2005;13:3127–39
   PubMed Web of Science ®Google Scholar
• Barazandeh Tehrani M, Emami S, Asadi M, et al Imidazo[2,1-b]thiazole derivatives as new inhibitors of 15-lipoxygenase. Eur J Med Chem 2014;87:759–64
   PubMed Web of Science ®Google Scholar
• Hofmann B, Franke L, Proschak E, et al Scaffold-hopping cascade yields potent inhibitors of 5-lipoxygenase. ChemMedChem 2008;3:1535–8
   PubMed Web of Science ®Google Scholar
• Wisniewska JM, Rödl CB, Kahnt AS, et al Molecular characterization of EP6-a novel imidazo[1,2-a]pyridine based direct 5-lipoxygenase inhibitor. Biochem Pharmacol 2012;83:228–40
   PubMed Web of Science ®Google Scholar
• Dubé D, Blouin M, Brideau C, et al Quinolines as potent 5-lipoxygenase inhibitors: synthesis and biological profile of L-746,530. Bioorg Med Chem Lett 1998;8:1255–60
   PubMed Web of Science ®Google Scholar
• Werz O, Greiner C, Koeberle A, et al Novel and potent inhibitors of 5-lipoxygenase product synthesis based on the structure of pirinixic acid. J Med Chem 2008;51:5449–53
   PubMed Web of Science ®Google Scholar
• Golitzer K, Fabian J, Frohberg P, Drutkowski G. Pyrrolo[2,3-c]quinolones and pyrrolo[3,4-d]qunolines-synthesis and investigation of lipoxygenase inhibition. Pharmazie 2002;57:243–9
   PubMed Web of Science ®Google Scholar
• White JD, Yager KM, Stappenbeck F. Synthesis and conformation of 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]quinolone, a 5-lipoxygenase inhibitor and leukotriene antagonist. J Med Chem 1993;58:3466–8
   Web of Science ®Google Scholar
• Musser JH, Kreft AF. 5-lipoxygenase: properties, pharmacology, and the quinolinyl(bridged)aryl class of inhibitors. J Med Chem 1992;35:2501–24
   PubMed Web of Science ®Google Scholar
• Mouradzadegun A, Ma’mani L, Mahdavi M, et al Sulfamic acid-functionalized hydroxyapatite encapsulated g-Fe2O3 nanoparticles as a magnetically recoverable catalyst for synthesis of N-fused imidazole-quinoline conjugates under solvent-free condition. RSC Adv 2015;5:83530–7
   Web of Science ®Google Scholar
• Dianat S, Mahdavi M, Moghimi S, et al Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds. Mol Divers 2015;19:797–805
   PubMed Web of Science ®Google Scholar
• Baruah B, Bhuyan PJ. Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramolecular domino hetero Diels–Alder reactions of 1-oxa-1,3-butadienes in aqueous medium. Tetrahedron 2009;65:7099–104
   Web of Science ®Google Scholar
• Malterud KE, Rydland KM. Inhibitors of 15-lipoxygenase from orange peel. J Agric Food Chem 2000;48:5576–80
   PubMed Web of Science ®Google Scholar
• Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61
   PubMed Web of Science ®Google Scholar
• Mahdavi M, Shirazi MS, Taherkhani R, et al Synthesis, biological evaluation and docking study of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors. Eur J Med Chem 2014;82:308–13
   PubMed Web of Science ®Google Scholar