Synthesis and biological evaluation of novel angular fused pyrrolocoumarins

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 23, Issue 1, 2008, Pages 43-49

  Kontogiorgis, Christos ^a   Litinas, Konstantinos E ^a   Makri, Aristea ^a   Nicolaides, Demetrios N ^a   Vronteli, Anastasia ^a   Hadjipavlou Litina, Dimitra J ^a   Pontiki, Eleni ^a   Siohou, Asimoula ^b  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b Alexandrion Technological Educational Institution   (Greece)

Author keywords

Anti inflammatory activity; Antioxidant activity; Dimethylacetylenedicarboxylate; Hydroxyindoles; Pyrrrolocoumarins; Triphenylphosphine

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 5 HYDROXYINDOLE; CAFFEIC ACID; CARRAGEENAN; COUMARIN; COUMARIN DERIVATIVE; INDOMETACIN; LIPOXYGENASE; METHYL 2 OXO 2,7 DIHYDROPYRANO[2,3 E]INDOLE 4 CARBOXYLATE; METHYL 7 OXO 3,7 DIHYDROPYRANO[2,3 E]INDOLE 9 CARBOXYLATE; METHYL 7 OXO 3,7,8,9 TETRAHYDROPYRANO[2,3 E]INDOLE 9 CARBOXYLATE; NORDIHYDROGUAIARETIC ACID; PYRROLOCOUMARIN DERIVATIVE; TROLOX C; UNCLASSIFIED DRUG; WARFARIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; HUMAN; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PAW EDEMA; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RAT;

ANTI-INFLAMMATORY AGENTS; ANTIOXIDANTS; COUMARINS; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; HUMANS; LIPOXYGENASE; PROTHROMBIN TIME; PYRROLES; SOYBEANS;

EID: 39349093150     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701400801     Document Type: Article

References (34)

1. Murray, DH, Mendez, J. and Brown, SA (1982) The natural coumarins: occurrence, chemistry and biochemistry, J. Wiley & Sons, N. York
2. O'Kennedy, R. and Thornes, RD (1997) Coumarins: Biology, applications and mode of action, J. Wiley & Sons, Chichester
3. Fylaktakidou, KC, Hadjipavlou-Litina, DJ, Litinas, KE and Nicolaides, DN (2004) Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activity. Curr Pharm Des, 10, pp. 3813-3833.
4. Dall'Acqua, F. and Vedaldi, D. (1995) CRC handbook of organic photochemistry and photobiology, pp. 1341-1350. CRC Press, Boca Raton, FL
5. Santana, L., Uriarte, E., Via, L Dalla and Gia, O. (2000) A new benzoangelicin with strong photobiological activity. Bioorg Med Chem Lett, 10, pp. 135-137.
6. Guiotto, A., Chilin, A., Manzini, P., Dall'Acqua, F., Bordin, F. and Rodighiero, P. (1995) Synthesis and antiproliferative activity of furocoumarin isosters Il Farmaco. 50, pp. 479-488.
7. Ploypradith, P., Mahidol, C., Sahakitpichan, P., Wongbundit, S. and Ruchirawat, S. (2004) 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, 43, pp. 866-868.
8. Meyer, H. (1975) Studies on coumarins. Pyrrolocoumarins. Acta Chem Scand, Ser B, 29, pp. 133-140.
9. Khoshtariya, TE, Kurkovsaya, LN, Bochoidze, LT, Batsikadze, KT, Mirziashvili, NT, Abesadze, IG, Sikharulidze, MI, Turabelidze, VG, Ananiashvili, VO, Dzhashi, TO and Maisuradze, MG (2005) 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, 41, pp. 208-215.
10. Suslov, VV, Gordeev, EN and Traven, VF (2004) Novel schemes for the synthesis of pyrrolocoumarins. Chem Heterocyclic Comp, 40, pp. 1315-1322.
11. Rodighiero, P., Chili, A., Pastorini, G. and Guiotto, A. (1987) Pyrrolocoumarin derivatives as potential photoreagents toward DNA J Heterocyclic Chem, 24, pp. 1041-1043.
12. Khan, MA and Morley, ML de B. (1979) Condensed benzopyrans. IV. Synthesis of some derivatives of 7H- and 9H-pyrano[3,2-e]indoles. J Heterocyclic Chem, 16, pp. 997-999.
13. Majumdar, KC and Ghosh, SK (1994) Studies on amine oxide rearrangements: Regioselective synthesis of pyrano[3,2-e]indol-7-one. J Chem Soc Perkin Trans, 1, pp. 2889-2894.
14. Gonzales, JC, Lobo-Antunes, J., Perez-Lourido, P., Santana, L. and Uriarte, E. (2002) Synthesis of angular pyrrolocoumarins Synthesis, pp. 475-478.
15. Hiremath, SP, Badiger, GR, Jivanagi, AS and Purohit, MG (1992) Synthesis, spectral and biological studies of oxazinono and pyrono indoles. Ind J Chem, pp. 583-589.
16. Hiremath, SP, Badami, PS and Purohit, MG (1983) 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, pp. 437-440.
17. Nicolaides, DN, Bezergiannidou-Balouctsi, C., Awad, R Wagih, Litinas, KE, Malamidou-Xenikaki, E., Terzis, A. and Raptopoulou, CP (1997) Site-selective Diels-Alder reactions of 7-(methoxyimino)-4-methylchromene-2,8-dione with alkenes. J Org Chem, 62, pp. 499-502.
18. Nicolaides, DN, Fylaktakidou, KC, Litinas, KE and Adamopoulos, SG (1998) The synthesis of some pyrano[2,3-g]chromene-2,7-diones and furo[2,3-g]chromen-6-ones. J Heterocyclic Chem, 35, pp. 91-96.
19. Nicolaides, DN, Gautam, DR, Litinas, KE, Manouras, C. and Fylaktakidou, KC (2001) Reactions of 2-(methoxyimino)benzen-1-ones with a-alkylethoxycarbonylmethylene(triphenyl)phosphoranes Tetrahedron, 57, pp. 9469-9474.
20. Nicolaides, DN, Gautam, DR, Litinas, KE and Papamehael, T. (2002) Synthesis of some 3,4-dihydro-2H-benzo[f]pyrano[2,3-h]chromen-6-one derivatives. J Chem Soc Perkin Trans, 1, pp. 1455-1460.
21. Fylaktakidou, KC, Gautam, DR, Hadjipavlou-Litina, DJ, Kontogiorgis, CA, Litinas, KE and Nicolaides, DN (2001) 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, 1, pp. 3073-3079.
22. Kontogiorgis, C. and Hadjipavlou-Litina, D. (2003) Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/ antioxidants agents. J Enz Inhib Med Chem, 18, pp. 63-69.
23. Nicolaides, DN, Gautam, DR, Litinas, KE, Hadjipavlou-Litina, DJ and Fylaktakidou, KC (2004) Synthesis and evaluation of the antioxidant and anti-inflammatory activities of some benzo[l]khellactone derivatives and analogues. Eur J Med Chem, 39, pp. 323-332.
24. Kontogiorgis, CA and Hadjipavlou-Litina, DJ (2005) Synthesis and anti-inflammatory activity of coumarin derivatives. J Med Chem, 48, pp. 6400-6408.
25. Candan, F. (2003) Effect of Rhus coribum L. (Aracardiaceae) on superoxide radical scavenging and xanthine oxidase activity. J Enz Inhib Med Chem, 18, pp. 59-62.
26. Quick, AJ (1935) The prothrombin in hemophilia and in obstructive jaundice. J Biol Chem, 109, pp. 73-74.
27. Proctor, RR and Rapaport, SI (1961) The partial thromboplastin time with kaolin. A simple screening test for first stage plasma clotting factor deficiencies. Amer J Clin Path, 36, pp. 212-219.
28. Baldoumi, V., Gautam, DR, Litinas, KE and Nicolaides, DN (2006) 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, 62, pp. 8016-8020.
29. Yavari, I., Adib, M. and Hojabri, L. (2002) Vinyltriphenylphosphonium salt mediated synthesis of 1,4-benzoxazine and coumarin derivatives. Tetrahedron, 58, pp. 6895-6899.
30. 5 -phosphaphenanthrenes, and benzochromene derivatives. Org Biomol Chem, 1, pp. 560-564.
31. Day, RO, Graham, GG, Williams, KM and Brooks, PM (1988) Variability in response to NSAIDs. Fact or fiction? Drugs, pp. 643-651.
32. Ellis, GA and Blake, DR (1993) Why are non-steroidal anti-inflammatory drugs so variable in their efficacy? A description of ion trapping. Ann Rheum Dis, pp. 241-243.
33. Muller, K. (1994) 5-lipoxygennase and 12-lipoxygenase: Attractive targets for the development of novel antipsoriatic drugs, reviews and trends. Archiv Pharm, 327, pp. 3-19.
34. Chapelev, LL, Beshara, CS, MacLean, PD, Hartfield, GL, Raud, AA, Thompson, A., Wright, JS and Barclay, LRC (2006) 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, 71, pp. 22-30.