Synthesis and biological evaluation of fused oxepinocoumarins as free radicals scavengers

References

• Murray DH, J. Mendez, J, Brown SA. The Natural Coumarins: Occurrence, Chemistry and Biochemistry. New York: Wiley, 1982.
   Google Scholar
• O’Kennedy R, Thornes RD. Coumarins: Biology, Applications and Mode of Action. Chichester: Wiley, 1997.
   Google Scholar
• Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr Pharm Des 2004;10:3813–3833.
   PubMed Web of Science ®Google Scholar
• Dall’Acqua F, Vedaldi D. Molecular basis of psoralen photochemotherapy. In: Horspool WM, Song PS, eds., CRC Handbook of Organic Photochemistry and Photobiology. Boca Raton, FL: CRC Press, 1995, pp. 1341–1350.
   Google Scholar
• Santana L, Uriarte E, Roleira F, Milhazes N, Borges F. Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity. Curr Med Chem 2004;11:3239–3261.
   PubMed Web of Science ®Google Scholar
• Kulkarni MV, Kulkarni GM, Lin CH, Sun CM. Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Curr Med Chem 2006;13:2795–2818.
   PubMed Web of Science ®Google Scholar
• Wulff H, Rauer H, Düring T, Hanselmann C, Ruff K, Wrisch A et al. Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: synthesis and photoreactivity. J Med Chem 1998;41:4542–4549.
   PubMed Web of Science ®Google Scholar
• Chimichi S, Boccalini M, Cosimelli B, Viola G, Vedaldi D, Dall’ Acqua F. A convenient synthesis of psoralens. Tetrahedron 2002;58:4859–4863.
   Google Scholar
• Kitamura N, Kohtani S, Nakagaki R. Molecular aspects of furocoumarin reactions: Photophysics, photochemistry, photobiology, and structural analysis. J Photochem Photobiol C Photochem Rev 2005;6:168–185.
   Web of Science ®Google Scholar
• Mali RS, Pandhare NA, Sindkhedkar MD. Convenient two-step syntheses of seselin and angelicin derivatives. Tetrahedron Lett 1995;36:7109–7110.
   Web of Science ®Google Scholar
• Santana L, Uriarte E, Dalla Via L, Gia O. A new benzoangelicin with strong photobiological activity. Bioorg Med Chem Lett 2000;10:135–137.
   PubMed Web of Science ®Google Scholar
• Mali RS, Joshi PP, Sandhu PK, Manekar-Tilve A. Efficient syntheses of 6-prenylcoumarins and linear pyranocoumarins: Total synthesis of suberosin, toddaculin, O-methylapigravin (O-methylbrosiperin), O-methylbalsamiferone, dihydroxanthyletin, xanthyletin and luvangetin J Chem Soc Perkin Trans 2002;1:371–376.
   Google Scholar
• Xie L, Takeuchi Y, Cosentino LM, McPhail AT, Lee KH. Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3′R,4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues. J Med Chem 2001;44:664–671.
   PubMed Web of Science ®Google Scholar
• Nicolaides DN, Gautam DR, Litinas KE, Hadjipavlou-Litina DJ, Fylaktakidou KC. Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues. Eur J Med Chem 2004;39:323–332.
   PubMed Web of Science ®Google Scholar
• Moody CJ. Claisen Rearrangement in heteroaromatic systems. In: Katritzky AR, ed., Advances in Heterocyclic Chemistry, Vol. 42. Orlando, FL: Academic Press, 1987, p. 231.
   Google Scholar
• Lutz RP. Catalysis of cope and claisen rearrangements. Chem Rev 1984;84:205–247.
   Web of Science ®Google Scholar
• Saidi MR, Bigdeli K. Microwave promoted and improved thermal synthesis of pyranocoumarins and furocoumarins. J Chem Res 1998;800–801.
   Google Scholar
• Saidi MR, Rajabi F. Microwave and BF3 promoted rearrangement of allyloxycoumarins to allylcoumarins and dihydrofurocoumarins. Heterocycles 2001;55:1805–1812.
   Google Scholar
• Zhang Q, Chen Y, Xia Y, Yang Z, Xia P. Thermal ring closure reaction of 4-methyl-7-(1,1-disubstituted propyn-2-yloxy)chromen-2-ones: the effects of the substituents at propargylic position on reactivity and products. Synth Commun 2004;34:4507–4515.
   Web of Science ®Google Scholar
• Garazd MM, Garazd YL, Khilya VP. Neoflavones. 2. Methods for synthesizing and modifying 4-arylcoumarins. Chem Nat Comp 2005;41:245–271.
   Google Scholar
• Litinas KE, Symeonidis T. Convenient synthesis of fused pyran[3,2-h]- and furo[3,2-h]coumarins from naphthalene-2,3-diol. Tetrahedron 2010;66:1289–1293.
   Google Scholar
• Grubbs RH, Chang S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998;54:4413–4450.
   Web of Science ®Google Scholar
• Armstrong SK. Ring closing diene metathesis in organic synthesis. J Chem Soc Perkin Trans 1998;1:371–388.
   Google Scholar
• Fürstner A. Olefin Metathesis and Beyond. Angew Chem Int Ed Engl 2000;39:3012–3043.
   PubMed Web of Science ®Google Scholar
• Deiters A, Martin SF. Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis. Chem Rev 2004;104:2199–2238.
   PubMed Web of Science ®Google Scholar
• Vougioukalakis GC, Grubbs RH. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts. Chem Rev 2010;110:1746–1787.
   PubMed Web of Science ®Google Scholar
• Chattopadhyay SK, Maity S, Panja S. Combined Claisen rearrangement and ring-closing metathesis as a route to oxepin- and oxocin-annulated coumarins. Tetrahedron Lett 2002;43:7781–7783.
   Google Scholar
• van Otterlo WAL, Ngidi EL, de Koning CB. Sequential isomerisation and ring-closing metathesis: Masked styryl and vinyloxyaryl groups for the synthesis of benzo-fused heterocycles. Tetrahedron Lett 2003;44:6483–6486.
   Google Scholar
• Tsai T-W, Wang E-C. A new synthesis of angelicin from 7-hydroxycoumarin via C-propenation-O-vinylation and ring-closing metathesis. J Chin Chem Soc 2004;51:1019–1023.
   Google Scholar
• Virolleaud M-A, Piva O. Selective formation of dihydropyran derivatives by a tandem domino ring-closing metathesis/cross-metathesis. Tetrahedron Lett 2007;48:1417–1420.
   Google Scholar
• Snyder NL, Haines HM, Peczuh MW. Recent developments in the synthesis of oxepins. Tetrahedron 2006;62:9301–9320.
   Google Scholar
• Majumdar KC, Rahaman H, Islam R, Roy B. Tandem Claisen rearrangement and ruthenium catalyzed enyne bond reorganization as a route to the synthesis of tricyclic 1,8-naphthyridinones. Tetrahedron Lett 2006;47:2111–2113.
   Google Scholar
• Chattopadhyay SK, Roy SP, Ghosh D, Biswas G. Synthesis of oxepine-, oxocine- and azepine-annulated carbazole derivatives by combined Claisen rearrangement and diene/enyne metathesis. Tetrahedron Lett 2006;47:6895–6898.
   Web of Science ®Google Scholar
• Chattopadhyay SK, Dey R, Biswas S. Regioselective synthesis of oxepin- and oxocin-annulated 2-quinolones. Synthesis 2005;403–406.
   Google Scholar
• Buszek KR, Sato N, Jeong Y. Total synthesis of octalactin A via ring-closing metathesis reaction. Tetrahedron Lett 2002;43:181–184.
   Google Scholar
• Fürstner A, Langemann K. Conformationally Unbiased Macrocyclization Reactions by Ring Closing Metathesis. J Org Chem 1996;61:3942–3943.
   PubMed Web of Science ®Google Scholar
• Litinas KE, Salteris BE. Unsaturated macrocyclic lactone synthesis via catalytic ring-closing metathesis. J Chem Soc Perkin Trans 1997;1:2869–2872.
   Google Scholar
• Mohapatra DK, Ramesh DK, Giardello MA, Chorghade MS, Gurjar MK, Grubbs RH. Protecting group directed ring-closing metathesis (RCM): the first total synthesis of an anti-malarial nonenolide. Tetrahedron Lett 2007;48:2621–2625.
   Google Scholar
• Baldoumi V, Gautam DR, Litinas KE, Nicolaides DN. Convenient synthesis of linear pyrano[3,2-g]-, [2,3-g]- and angular pyrano[3,2-f]coumarins from 4[(1,1-dimethyl-2-propynyl)oxy]phenol. Tetrahedron 2006;62:8016–8020.
   Web of Science ®Google Scholar
• Kontogiorgis C, Litinas KE, Makri A, Nicolaides DN, Vronteli A, Hadjipavlou-Litina DJ et al. Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins. J Enzyme Inhib Med Chem 2008;23:43–49.
   PubMed Web of Science ®Google Scholar
• Symeonidis T, Chamilos M, Hadjipavlou-Litina DJ, Kallitsakis M, Litinas KE. Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors. Bioorg Med Chem Lett 2009;19:1139–1142.
   PubMed Web of Science ®Google Scholar
• Gallos JK, Koftis TV, Sarli VC, Litinas KE. A straightforward synthesis of perbenzylated conduritols from alditols by ring closing olefin metathesis. J Chem Soc Perkin Trans 1999; 1:3075–3077.
   Google Scholar
• Halliwell B. Drug antioxidant effects. A basis for drug selection? Drugs 1991;42:569–605.
   PubMed Web of Science ®Google Scholar
• Saldanha LA, Elias G, Rao MN. Oxygen radical scavenging activity of phenylbutenones and their correlation with antiinflammatory activity. Arzneimittelforschung 1990;40:89–91.
   PubMed Web of Science ®Google Scholar
• Loutfy MA. The Claisen rearrangement of umbelliferone allyl ether. Pharmazie 1979;34:672.
   Google Scholar
• Kaufman KD. Synthetic Furocoumarins. I. A new synthesis of methyl-substituted psoralenes and isopsoralenes. J Org Chem 1961;26:117–121.
   Web of Science ®Google Scholar
• Kaufman KD, Keana JFW, Kelly RC, McBride DW, Slomp G. Synthetic furocoumarins. VI Analogs of psoralene derived from hydroquinone. J Org Chem 1962;27:2567–2572.
   Web of Science ®Google Scholar
• Guiotto A, Manzini P, Chilin A, Pastorini G, Rodighiero P. 13C-NMR spectra and carbon–proton coupling constants of variously annulated furocoumarins. J Heterocyclic Chem 1985;22:649–656.
   Google Scholar
• Symeonidis T, Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE. Synthesis and anti-inflammatory evaluation of novel angularly or linearly fused coumarins. Eur J Med Chem 2009;44:5012–5017.
   PubMed Web of Science ®Google Scholar
• Baker W, Lothian OM. Studies in chelation. Part II. The stabilisation of Kekulé forms in o-hydroxyacetophenones. J Chem Soc 1935;628–633.
   Google Scholar
• Kulisic T, Radonic A, Katalinic V, Milos M. Use of different methods for testing antioxidative activity of oregano essential oil. Food Chem 2004;85:633–640.
   Web of Science ®Google Scholar
• Halliwell B, Gutterridge JMC. Free Radicals in Biology and Medicine. Oxford: Clarendon, 1989.
   Google Scholar
• Kuhn H, Belkner J, Wiesner R, Brash AR. Oxygenation of biological membranes by the pure reticulocyte lipoxygenase. J Biol Chem 1990;265:18351–18361.
   PubMed Web of Science ®Google Scholar
• Shureiqi I, Lippman SM. Lipoxygenase modulation to reverse carcinogenesis. Cancer Res 2001;61:6307–6312.
   PubMed Web of Science ®Google Scholar
• Zhao L, Funk CD. Lipoxygenase pathways in atherogenesis. Trends Cardiovasc Med 2004;14:191–195.
   PubMed Web of Science ®Google Scholar
• Müller K. 5-Lipoxygenase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs. Arch Pharm (Weinheim) 1994;327:3–19.
   PubMed Web of Science ®Google Scholar
• Curini M, Epifano F, Genovese S, Menghini L, Ricci D, Fraternale D, Giamperi L, Bucchini A, Bellacchio E. Lipoxygenase inhibitory activity of boropinic acid, active principle from Boronia pinnata. Nat Prod Commun 2006:1141–1145.
   Google Scholar
• Pontiki E, Hadjipavlou-Litina D. Lipoxygenase inhibitors: a comparative QSAR study review and evaluation of new QSARs. Med Res Rev 2008;28:39–117.
   PubMed Web of Science ®Google Scholar