Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins

References

• Murray DH, Mendez J, Brown SA. The natural coumarins: occurrence, chemistry and biochemistry. J. Wiley & Sons, N. York 1982
   Google Scholar
• O'Kennedy R, Thornes RD. Coumarins: Biology, applications and mode of action. J. Wiley & Sons, Chichester 1997
   Google Scholar
• Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activity. Curr Pharm Des 2004; 10: 3813–3833
   PubMed Web of Science ®Google Scholar
• Dall'Acqua F, Vedaldi D. CRC handbook of organic photochemistry and photobiology, WM Horspool, PS Song. CRC Press, Boca Raton, FL 1995; 1341–1350
   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
• Guiotto A, Chilin A, Manzini P, Dall'Acqua F, Bordin F, Rodighiero P. Synthesis and antiproliferative activity of furocoumarin isosters Il Farmaco. 1995; 50: 479–488
   Google Scholar
• Ploypradith P, Mahidol C, Sahakitpichan P, Wongbundit S, Ruchirawat S. A highly efficient synthesis of Lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes. Angew Chem Int Ed 2004; 43: 866–868
   PubMed Web of Science ®Google Scholar
• Meyer H. Studies on coumarins. Pyrrolocoumarins. Acta Chem Scand, Ser B 1975; 29: 133–140
   PubMedGoogle Scholar
• Khoshtariya TE, Kurkovsaya LN, Bochoidze LT, Batsikadze KT, Mirziashvili NT, Abesadze IG, Sikharulidze MI, Turabelidze VG, Ananiashvili VO, Dzhashi TO, Maisuradze MG. Pyrrolocoumarins. 1. Synthesis and spectroscopic investigation of 7-oxo- and 1,2,7-trioxo-1,2-dihydropyrano[3,2-e]indole and their derivatives. Chem Heterocyclic Comp 2005; 41: 208–215
   Google Scholar
• Suslov VV, Gordeev EN, Traven VF. Novel schemes for the synthesis of pyrrolocoumarins. Chem Heterocyclic Comp 2004; 40: 1315–1322
   Google Scholar
• Rodighiero P, Chili A, Pastorini G, Guiotto A. Pyrrolocoumarin derivatives as potential photoreagents toward DNA J Heterocyclic Chem 1987; 24: 1041–1043
   Google Scholar
• Khan MA, de B Morley ML. Condensed benzopyrans. IV. Synthesis of some derivatives of 7H- and 9H-pyrano[3,2-e]indoles. J Heterocyclic Chem 1979; 16: 997–999
   Web of Science ®Google Scholar
• Majumdar KC, Ghosh SK. Studies on amine oxide rearrangements: Regioselective synthesis of pyrano[3,2-e]indol-7-one. J Chem Soc Perkin Trans 1994; 1: 2889–2894
   Google Scholar
• Gonzales JC, Lobo-Antunes J, Perez-Lourido P, Santana L, Uriarte E. Synthesis of angular pyrrolocoumarins Synthesis 2002; 475–478
   Google Scholar
• Hiremath SP, Badiger GR, Jivanagi AS, Purohit MG. Synthesis, spectral and biological studies of oxazinono and pyrono indoles. Ind J Chem 1992; B31: 583–589
   Google Scholar
• Hiremath SP, Badami PS, Purohit MG. Synthesis of substituted 1H-3,4-dihydro[1,2]diazepino[4,5,6-cd]indol-3-ones, 3,7-dihydropyrano[3,2-e]indol-7-ones and 6H-oxazolo[4,5-e]indoles. Indian J Chem 1983; B22: 437–440
   Google Scholar
• Nicolaides DN, Bezergiannidou-Balouctsi C, Wagih Awad R, Litinas KE, Malamidou-Xenikaki E, Terzis A, Raptopoulou CP. Site-selective Diels-Alder reactions of 7-(methoxyimino)-4-methylchromene-2,8-dione with alkenes. J Org Chem 1997; 62: 499–502
   PubMed Web of Science ®Google Scholar
• Nicolaides DN, Fylaktakidou KC, Litinas KE, Adamopoulos SG. The synthesis of some pyrano[2,3-g]chromene-2,7-diones and furo[2,3-g]chromen-6-ones. J Heterocyclic Chem 1998; 35: 91–96
   Web of Science ®Google Scholar
• Nicolaides DN, Gautam DR, Litinas KE, Manouras C, Fylaktakidou KC. Reactions of 2-(methoxyimino)benzen-1-ones with a-alkylethoxycarbonylmethylene(triphenyl)phosphoranes Tetrahedron 2001; 57: 9469–9474
   Web of Science ®Google Scholar
• Nicolaides DN, Gautam DR, Litinas KE, Papamehael T. Synthesis of some 3,4-dihydro-2H-benzo[f]pyrano[2,3-h]chromen-6-one derivatives. J Chem Soc Perkin Trans 2002; 1: 1455–1460
   Google Scholar
• Fylaktakidou KC, Gautam DR, Hadjipavlou-Litina DJ, Kontogiorgis CA, Litinas KE, Nicolaides DN. Reactions of 4-methylchromene-2,7,8-trione with phosphonium ylides. Synthesis and evaluation of fused 1,3-dioxolocoumarins as antioxidants and antiinflammatories. J Chem Soc Perkin Trans 2001; 1: 3073–3079
   Google Scholar
• Kontogiorgis C, Hadjipavlou-Litina D. Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidants agents. J Enz Inhib Med Chem 2003; 18: 63–69
   PubMed Web of Science ®Google Scholar
• Nicolaides DN, Gautam DR, Litinas KE, Hadjipavlou-Litina DJ, Fylaktakidou KC. Synthesis and evaluation of the antioxidant and anti-inflammatory activities of some benzo[l]khellactone derivatives and analogues. Eur J Med Chem 2004; 39: 323–332
   PubMed Web of Science ®Google Scholar
• Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and anti-inflammatory activity of coumarin derivatives. J Med Chem 2005; 48: 6400–6408
   PubMed Web of Science ®Google Scholar
• Candan F. Effect of Rhus coribum L. (Aracardiaceae) on superoxide radical scavenging and xanthine oxidase activity. J Enz Inhib Med Chem 2003; 18: 59–62
   PubMed Web of Science ®Google Scholar
• Quick AJ. The prothrombin in hemophilia and in obstructive jaundice. J Biol Chem 1935; 109: 73–74
   Google Scholar
• Proctor RR, Rapaport SI. The partial thromboplastin time with kaolin. A simple screening test for first stage plasma clotting factor deficiencies. Amer J Clin Path 1961; 36: 212–219
   PubMed Web of Science ®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
   Google Scholar
• Yavari I, Adib M, Hojabri L. Vinyltriphenylphosphonium salt mediated synthesis of 1,4-benzoxazine and coumarin derivatives. Tetrahedron 2002; 58: 6895–6899
   Web of Science ®Google Scholar
• Yavari I, Anary-Abbasinejad M, Hossaini Z. Reaction between naphthols and dimethyl acetylene dicarboxylate in the presence of phosphites. Synthesis of stable oxa-2λ5-phosphaphenanthrenes, and benzochromene derivatives. Org Biomol Chem 2003; 1: 560–564
   PubMed Web of Science ®Google Scholar
• Day RO, Graham GG, Williams KM, Brooks PM. Variability in response to NSAIDs. Fact or fiction? Drugs 1988; 643–651
   Google Scholar
• Ellis GA, Blake DR. Why are non-steroidal anti-inflammatory drugs so variable in their efficacy? A description of ion trapping. Ann Rheum Dis 1993; 241–243
   PubMed Web of Science ®Google Scholar
• Muller K. 5-lipoxygennase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs, reviews and trends. Archiv Pharm 1994; 327: 3–19
   PubMed Web of Science ®Google Scholar
• Chapelev LL, Beshara CS, MacLean PD, Hartfield GL, Raud AA, Thompson A, Wright JS, Barclay LRC. Polypyrroles as antioxidants: Kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures. J Org Chem 2006; 71: 22–30
   PubMed Web of Science ®Google Scholar
• Biobyte Corp., C-QSAR Database 201 West 4th Str., Suite 204, Claremont, CA, California 91711, USA.
   Google Scholar