Synthesis and pharmacological activity of chalcones derived from 2,4,6-trimethoxyacetophenone in RAW 264.7 cells stimulated by LPS: Quantitative structure-activity relationships

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 2, 2008, Pages 658-667

  Chiaradia, Louise Domeneghini ^a   dos Santos, Rodrigo ^a   Vitor, Carlos Eduardo ^a   Vieira, André Alexandre ^a   Leal, Paulo César ^a   Nunes, Ricardo José ^a   Calixto, João Batista ^a   Yunes, Rosendo Augusto ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Antiinflammatory; Chalcones; iNOS inhibitor; Nitric oxide; QSAR

Indexed keywords

3 (1,3 BENZODIOXOL 5 YL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (2 CHLOROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (2 NAPHTHYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (2 NITROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (2,6 DICHLOROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (3 CHLOROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (3 NITROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (3,4 DICHLOROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (4 BUTOXYPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (4 CHLOROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (4 METHOXYPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 (4 NITROPHENYL) 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; 3 [4 (DIMETHYLAMINO)PHENYL] 1 (2',4',6' TRIMETHOXYPHENYL) 2 PROPEN 1 ONE; ACETOPHENONE DERIVATIVE; ALDEHYDE; ANTIINFLAMMATORY AGENT; CHALCONE DERIVATIVE; ENDOTHELIAL NITRIC OXIDE SYNTHASE; ENZYME INHIBITOR; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 1; LIPOPOLYSACCHARIDE; N [3 (AMINOMETHYL)BENZYL]ACETAMIDINE; NITRIC OXIDE; NITRITE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL VIABILITY; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONFIDENCE INTERVAL; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; ELECTRON; IC 50; IN VITRO STUDY; MACROPHAGE; MOUSE; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ACETOPHENONES; ANIMALS; ANTI-INFLAMMATORY AGENTS; CHALCONES; INHIBITORY CONCENTRATION 50; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); MURINAE;

EID: 38549094205     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.039     Document Type: Article

References (32)

1. Coleman J.W. Int. Immunopharmacol. 1 (2001) 1397-1406
2. Moncada S., Palmer R.M., and Higgs E.A. Pharmacol. Rev. 43 (1991) 109-142
3. Bogdan C., Rollinghoff M., and Diefenbach A. Immunol. Rev. 173 (2000) 17-26
4. MacMicking J., Xie Q.C., and Nathan C. Annu. Rev. Immunol. 15 (1997) 323-350
5. Xie Q.W., Cho H.J., Calaycay J., Mumford R.A., Swiderek K.M., Lee T.D., et al. Science 256 (1992) 225-228
6. Vogel A.I. Vogel's Textbook of Practical Organic Chemistry. 5th ed. (1989), John Wiley & Sons, New York p 1017
7. Dimmock J.R., Elias D.W., Beazely M.A., and Kandepu N.M. Curr. Med. Chem. 6 (1999) 1125-1149
8. Ni L., Meng C.Q., and Siroski J.A. Expert Opin. Ther Patents 14 (2004) 1669-1691
9. Lopez S.N., Castelli M.V., Zacchino S.A., Dominguez J.N., Lobo G., Charris-Charris J., Cortes J.C.G., Ribas J.C., Devia C., Rodriguez A.M., and Enriz R.D. Bioorg. Med. Chem. 9 (2001) 1999-2013
10. Boeck P., Leal P.C., Yunes R.A., Cechinel-Filho V., López S., Sortino M., Escalante A., Furlán R.L.E., and Zacchino S. Arch. Pharm. 338 (2005) 87-95
11. Phrutivorapongkul A., Lipipun V., Ruangrungsi N., Kirtikara K., Nishikawa K., Maruyana S., Watanabe T., and Ishikawa T. Chem. Pharm. Bull. 51 (2003) 187-190
12. Lin Y.M., Zhou Y., Flavin M.T., Zhow L.M., Nie W., and Chen F.C. Bioorg. Med. Chem. 10 (2002) 2795-2802
13. Liu M., Wilairat P., and Go M. J. Med. Chem. 44 (2001) 4443-4452
14. Nielsen S.F., Christensen S.B., Cruciani G., Kharazmi A., and Liljefors T. J. Med. Chem. 41 (1998) 4819-4832
15. Bergmann, B. R.; Torres dos Santos, E. C.; Yunes, R. A.; Cechinel-Filho, V.; Boeck, P. Brazil PI 0204079-4. 2004, 40 p.
16. Corréa R., Pereira M.A.S., Buffon D., dos Santos L., Cechinel-Filho V., Santos A.R.S., and Nunes R.J. Arch. Pharm. Med. Chem. 334 (2001) 332-334
17. Rojas J., Domínguez J.N., Charris J.E., Lobo G.M., Payá M., and Ferrándiz M.L. Eur. J. Med. Chem. 37 (2002) 699-705
18. Won S.J., Liu C.T., Tsao L.T., Weng J.R., Ko H.H., Wang J.P., and Lin C.N. Eur. J. Med. Chem. 40 (2005) 103-112
19. Ko H.H., Tsao L.Y., Yu K.L., Liu C.T., Wang J.P., and Lin C.N. Bioorg. Med. Chem. 11 (2003) 105-111
20. Edwards M.L., Stemerick D.M., and Sunkara P.S. J. Med. Chem. 33 (1990) 1948-1954
21. Nam N.H., Kim Y., You Y.J., Hong D.H., Kim H.M., and Ahn B.Z. Eur. J. Med. Chem. 38 (2003) 179-187
22. Herencia F., Ferrándiz M.L., Ubeda A., Guillén I., Dominguez J.N., Charris J.E., Lobo G.M., and Alcaraz M.J. Free Radical Biol. Med. 30 (2001) 43-50
23. Batt D.G., Goodman R., Jones D.G., Kerr J.S., Mantegna L.R., McAllister C., Newton R.C., Nurnberg S., Welch P.K., and Covington M.B. J. Med. Chem. 36 (1993) 1434-1442
24. Cechinel V.F., Vaz Z.R., Zunino L., Calixto J.B., and Yunes R.A. Eur. J. Med. Chem. 31 (1996) 833-839
25. Garvey E.P., Oplinger J.A., Furfine E.S., Kiff R.J., Laszlo F., Whittle B.J.R., and Knowles R.G. J. Biol. Chem. 272 (1997) 4959-4963
26. Sakaguchi Y., Shirahase H., Ichikawa A., Kanda M., Nozaki Y., and Uehara Y. Life Sci. 75 (2004) 2257-2267
27. dos Santos R., Kuhnen C.A., and Yunes R.A. Arch. Pharm. Chem. Life Sci. 339 (2006) 227-237
28. Galeazzi R., Marucchini C., Orena M., and Zadra C. Bioorg. Med. Chem. 10 (2002) 1019-1025
29. Galeazzi R., Marucchini C., Orena M., and Zadra C. J. Mol. Struct. (Theochem) 640 (2003) 191-200
30. Spartan'04, Wavefunction, Inc., Irvine, CA, 2003.
31. Dewar M.J.S., Stewart J.J.P., Zocbisch E.G., and Healy E.G. J. Am. Chem. Soc. 107 (1985) 3902-3909
32. De Oliveira D.B., and Gáudio A.C. Quant. Struct.-Act. Relat. 19 (2000) 599-601