2-Arylbenzo[b]furan derivatives as potent human lipoxygenase inhibitors

References

• Funk CD, Cyrus T. 12/15-Lipoxygenase, oxidative modification of LDL and atherogenesis. Trends Cardiovasc Med 2001;11:116–24
   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
• Brash AR. Lipoxygenases: occurrence, Ffunctions, catalysis, and acquisition of substrate. J Biol Chem 1999;274:23679–82
   PubMed Web of Science ®Google Scholar
• Mandal AK, Skoch J, Bacskai BJ, et al. The membrane organization of leukotriene synthesis. Proc Natl Acad Sci USA 2004;101:6587–92
   PubMed Web of Science ®Google Scholar
• Fabre JE, Goulet JL, Riche E, et al. Transcellular biosynthesis contributes to the production of leukotrienes during inflammatory responses in vivo. J Clin Invest 2002;109:1373–80
   PubMed Web of Science ®Google Scholar
• Charlier C, Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem 2003;38:645–59
   PubMed Web of Science ®Google Scholar
• Harizi H, Corcuff JB, Gualde N. Arachidonic acid-derived eicosanoids: roles in biology and immunopathology. Trends Mol Med 2008;14:461–9
   PubMed Web of Science ®Google Scholar
• Nakamura M, Shimizu T. Leukotriene receptors. Chem Rev 2011;111:6231–98
   PubMed Web of Science ®Google Scholar
• Dobrian AD, Lieb DC, Cole BK, et al. Functional and pathological roles of the 12- and 15-lipoxygenases. Prog Lipid Res 2011;50:115–31
   PubMed Web of Science ®Google Scholar
• Sadeghian H, Jabbari A. 15-Lipoxygenase inhibitors: a patent review. Expert Opin Ther Pat 2016;26:65–88
   PubMed Web of Science ®Google Scholar
• Lawrence T, Willoughby DA, Gilroy DW. Anti-inflammatory lipid mediators and insights into the resolution of inflammation. Nat Rev Immunol 2002;2:787–95
   PubMed Web of Science ®Google Scholar
• Pergola C, Werz O. 5-Lipoxygenase inhibitors: a review of recent developments and patents. Expert Opin Ther Pat 2010;20:355–75
   PubMed Web of Science ®Google Scholar
• Joshi YB, Giannopoulos PF, Praticò D. The 12/15-lipoxygenase as an emerging therapeutic target for Alzheimer's disease. Trends Pharmacol Sci 2015;36:181–6
   PubMed Web of Science ®Google Scholar
• Funk CD. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001;294:1871–5
   PubMed Web of Science ®Google Scholar
• Chan FL, Choi HL, Chen ZY, et al. Induction of apoptosis in prostate cancer cell lines by a flavonoid, baicalin. Cancer Lett 2000;160:219–28
   PubMed Web of Science ®Google Scholar
• Chen CH, Huang LL, Huang CC, et al. Baicalein, a novel apoptotic agent for hepatoma cell lines: a potential medicine for hepatoma. Nutr Cancer 2000;38:287–95
   PubMed Web of Science ®Google Scholar
• Nie D, Tang K, Diglio C, Honn KV. Eicosanoid regulation of angiogenesis: role of endothelial arachidonate 12-lipoxygenase. Blood 2000;95:2304–11
   PubMed Web of Science ®Google Scholar
• Weinstein DS, Wen L, Ngu K, et al. Discovery of selective imidazole-based inhibitors of mammalian 15-lipoxygenase: Highly potent against human enzyme within a cellular environment. Bioorg Med Chem Lett 2007;17:5115–20
   PubMed Web of Science ®Google Scholar
• Ganesha R, Victor K, Ajit J, et al. Discovery of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1. J Med Chem 2010;53:7392–404
   PubMed Web of Science ®Google Scholar
• Weinstein DS, Liu W ,Gu Z, et al. Tryptamine and homotryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase. Bioorg Med Chem Lett 2005;15:1435–40
   PubMed Web of Science ®Google Scholar
• Jagtap UB, Bapat VA. Artocarpus: a review of its traditional uses, phytochemistry and pharmacology. J Ethnopharmacol 2010;129:142–66
   PubMed Web of Science ®Google Scholar
• Hakim EH, Achmad SA, Juliawaty LD, et al. Prenylated flavonoids and related compounds of the Indonesian Artocarpus (Moraceae). J Nat Med 2006;60:161–84
   PubMed Web of Science ®Google Scholar
• Takasugi M, Nagao S, Ueno S, et al. Moracin C and D, new phytoalexins from diseased mulberry. Chem Lett 1978;7:1239–40
   Web of Science ®Google Scholar
• Katritzky AR, Rees CW, Scriven EFV. Comprehensive heterocyclic chemistry II: a review of the literature, 1982–1995: the structure, reactions, synthesis, and uses of heterocyclic compounds. Pergamon: Oxford; 1996
   Google Scholar
• Navarro E, Alonso SJ, Trujillo J, et al. General behavior, toxicity, and cytotoxic activity of elenoside, a lignan from Justicia hyssopifolia. J Nat Prod 2001;64:134–5
   PubMed Web of Science ®Google Scholar
• Day S, Chiu N, Tsao L, et al. New lignan glycosides with potent antiinflammatory effect, isolated from Justicia ciliata. J Nat Prod 2000;63:1560–2
   PubMed Web of Science ®Google Scholar
• Craigo J, Callahan M, Huang RC, Delucia AL. Inhibition of human papillomavirus type 16 gene expression by nordihydroguaiaretic acid plant lignan derivatives. Antiviral Res 2000;47:19–28
   PubMed Web of Science ®Google Scholar
• Silva DHS, Pereira FC, Zanoni MVB, Yoshida M. Lipophyllic antioxidants from Iryanthera juruensis fruits. Phytochemistry 2001;57:437–42
   PubMed Web of Science ®Google Scholar
• Wu D, Mei H, Tan P, et al. Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus. Tetrahedron Lett 2015;56:4383–7
   Web of Science ®Google Scholar
• Lu W, Zhao X, Xu Z, et al. Development of a new colorimetric assay for lipoxygenase activity. Anal Biochem 2013;441:162–8
   PubMed Web of Science ®Google Scholar
• Zhao X, Lu W, Song C, Huang J. Detection of mammalian 5-lipoxygenase activity using the fluorescent probe dihydrorhodamine 1,2,3. Eur J Lipid Sci Tech 2014;116:119–25
   Web of Science ®Google Scholar
• Lu W, Xue Z, Zou S, Jin H. A fluorimetric assay for human reticulocyte 15-lipoxygenase-1 activity. Anal Biochem 2012;426:66–8
   PubMed Web of Science ®Google Scholar
• Pergola C, Jazzar B, Rossi A, et al. Cinnamyl-3,4-dihydroxy-α-cyanocinnamate is a potent inhibitor of 5-lipoxygenase. J Pharmacol Exp Ther 2011;338:205–13
   PubMed Web of Science ®Google Scholar
• Afonso PV, Janka-Junttila M, Lee YJ, et al. LTB 4 is a signal-relay molecule during neutrophil chemotaxis. Dev Cell 2012;22:1079–91
   PubMed Web of Science ®Google Scholar
• Boxio R, Bossenmeyer-Pourié C, Steinckwich N, et al. Mouse bone marrow contains large numbers of functionally competent neutrophils. J Leukoc Biol 2004;75:604–11
   PubMed Web of Science ®Google Scholar
• Helgadottir A, Manolescu A, Thorleifsson G, et al. The gene encoding 5-lipoxygenase activating protein confers risk of myocardial infarction and stroke. Nat Genet 2004;36:233–9
   PubMed Web of Science ®Google Scholar
• Whittle B. The use of changes in capillary permeability in mice to distinguish between narcotic and nonnarcotic analgesics. Br J Pharmacol Chemother 1964;22:246–53
   PubMed Web of Science ®Google Scholar
• Koo HJ, Lim KH, Jung HJ, Park EH. Anti-inflammatory evaluation of gardenia extract, geniposide and genipin. J Ethnopharmacol 2006;103:496–500
   PubMed Web of Science ®Google Scholar
• Morebise O, Fafunso MA, Makinde JM, et al. Antiinflammatory property of the leaves of Gongronema latifolium. Phytother Res 2002;16:75–7
   PubMed Web of Science ®Google Scholar
• Haeggström JZ, Funk CD. Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease. Chem Rev 2011;111:5866–98
   PubMed Web of Science ®Google Scholar
• Schaible AM, Traber H, Temml V, et al. Potent inhibition of human 5-lipoxygenase and microsomal prostaglandin E(2) synthase-1 by the anti-carcinogenic and anti-inflammatory agent embelin. Biochem Pharmacol 2013;86:476–86
   PubMed Web of Science ®Google Scholar
• Antonio DG, Ellinor K, Min W, et al, Leukotriene B4-induced changes in vascular permeability are mediated by neutrophil release of heparin-binding protein (HBP/CAP37/azurocidin). FASEB J 2009;23:1750–7
   PubMed Web of Science ®Google Scholar
• Albeena N, Malik AH, Mohammed Afzal Z. Atropa acuminata Royle Ex Lindl. blunts production of pro-inflammatory mediators eicosanoids, leukotrienes, cytokines in vitro and in vivo models of acute inflammatory responses. J Ethnopharmacol 2015;180:353–7
   Google Scholar