Synthesis, in silico docking experiments of new 2-pyrrolidinone derivatives and study of their anti-inflammatory activity

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 9, 2011, Pages 2888-2902

  Moutevelis Minakakis, Panagiota ^a   Papavassilopoulou, Eleni ^a   Michas, George ^a   Georgikopoulou, Kalliopi ^a   Ragoussi, Maria Eleni ^a   Neophytou, Niki ^a   Zoumpoulakis, Panagiotis ^c   Mavromoustakos, Thomas ^a   Hadjipavlou Litina, Dimitra ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^c INSTITUTE OF BIOLOGY   (Greece)

Author keywords

2 Pyrrolidinones; Anti inflammatory activity; LOX

Indexed keywords

(1H IMIDAZOL 1 YLMETHYL) 1 (PHENYLMETHYL) 2 PYRROLIDINONE; (1H IMIDAZOL 1 YLMETHYL) 1 [[2 [1 (PHENYLMETHYL) 1H 1,2,3,4 TETRAZOL 5 YL]PHENYL]METHYL] 2 PYRROLIDINONE; (1H IMIDAZOL 1 YLMETHYL) 1 [[3 (PHENYLMETHOXY)PHENYL]METHYL] 2 PYRROLIDINONE; (HYDROXYMETHYL) 1 (PHENYLMETHYL) 2 PYRROLIDINONE; (HYDROXYMETHYL) 1 [[2 [1 (PHENYLMETHYL) 1H 1,2,3,4 TETRAZOL 5 YL]PHENYL]METHYL] 2 PYRROLIDINONE; (HYDROXYMETHYL) 2 PYRROLIDINONE; 1 [(3 HYDROXYPHENYL)METHYL] (1H IMIDAZOL 1 YLMETHYL) 2 PYRROLIDINONE; 1H IMIDAZOLE 4 (5) CARBOXYLIC ACID, 1 [[5 OXO 1 (PHENYLMETHYL) PYRROLIDINYL]METHYL], PHENYLMETHYL ESTER; 1H IMIDAZOLE 4 CARBOXYLIC ACID, 1 [[1 [[4 (METHOXYCARBONYL)PHENYL]METHYL] 5 OXO PYRROLIDINYL]METHYL],PHENYLMETHYL ESTER; 1H IMIDAZOLE 4 CARBOXYLIC ACID, 1 [[1 [[4 (METHOXYCARBONYL)PHENYL]METHYL] 5 OXO PYRROLIDINYL]METHYL];PHENYLMETHYL ESTER; 2 PYRROLIDINECARBOXYLIC ACID, 5 OXO 1 [[2 [1 (PHENYLMETHYL) 1H 1,2,3,4 TETRAZOL 5 YL]PHENYL]METHYL]METHYL ESTER; 2 PYRROLIDINONE, (1H IMIDAZOL 1 YLMETHYL) 1 [[2 (1H 1,2,3,4 TETRAZOL 5 YL)PHENYL]METHYL]; 2 PYRROLIDONE DERIVATIVE; 5 [[(TRIETHYLSILYL)OXY]METHYL] 2 PYRROLIDINONE; ACETIC ACID, (5 OXO 2 PYRROLIDINYL)METHYL ESTER; BENZENESULFONIC ACID, 4 METHYL, [5 OXO 1 (PHENYLMETHYL) PYRROLIDINYL]METHYL ESTER; BENZENESULFONIC ACID, 4 METHYL, [5 OXO 1 [[2 [1 (PHENYLMETHYL) 1H 1,2,3,4 TETRAZOL 5 YL]PHENYL]METHYL] 2 PYRROLIDINYL]METHYL ESTER; BENZOIC ACID, 4 [[(1H IMIDAZOL 1 YLMETHYL) 5 OXO 1 PYRROLIDINYL]METHYL],METHYL ESTER; BENZOIC ACID, 4 [[(1H IMIDAZOL 1 YLMETHYL) 5 OXO 1 PYRROLIDINYL]METHYL],PHENYLMETHYL ESTER; BENZOIC ACID, 4 [[2 (HYDROXYMETHYL) 5 OXO 1 PYRROLIDINYL]METHYL],METHYL ESTER; BENZOIC ACID, 4 [[2 (HYDROXYMETHYL) 5 OXO 1 PYRROLIDINYL]METHYL],PHENYLMETHYL ESTER; BENZOIC ACID, 4 [[2 [(ACETYLOXY)METHYL] 5 OXO 1 PYRROLIDINYL]METHYL],METHYL ESTER; BENZOIC ACID, 4 [[2 [[[(4 METHYLPHENYL)SULFONYL]OXY]METHYL] 5 OXO 1 PYRROLIDINYL]METHYL],PHENYLMETHYL ESTER; BENZOIC ACID, 4 [[2 OXO 5 [[(TRIETHYLSILYL)OXY]METHYL] 1 PYRROLIDINYL]METHYL],PHENYLMETHYL ESTER; INDOMETACIN; METHYL 1 [(1,4 [(BENZYLOXY)CARBONYL]BENZYL 5 OXOTETRAHYDRO 1H PYRROL 2 YL)METHYL] 1H IMIDAZOLE 4 CARBOXYLATE; METHYL 1 [(1,4 [(BENZYLOXY)CARBONYL]BENZYL 5 OXOTETRAHYDRO 1H PYRROL 2 YL)METHYL] 1H IMIDAZOLE 5 CARBOXYLATE; PYRROLIDINECARBOXYLIC ACID, 5 OXO 1 [[3 (PHENYLMETHOXY)PHENYL]METHYL],METHYL ESTER; PYRROLIDINECARBOXYLIC ACID,5 OXO 1 (PHENYLMETHYL)METHYL ESTER; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CATALYSIS; COMPUTER MODEL; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HYDROGEN BOND; IC 50; LIPID PEROXIDATION; MOLECULAR DOCKING; NONHUMAN; PAW EDEMA; RAT; REACTION TIME;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BINDING SITES; CATALYTIC DOMAIN; COMPUTER SIMULATION; EDEMA; IMIDAZOLES; LIPOXYGENASES; PYRROLES; PYRROLIDINONES; RATS;

RATTUS;

EID: 79955420758     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.044     Document Type: Article

References (47)

1. L. Flohe, R. Beckman, H. Giertz, and G. Loschen Oxygen-centered Free Radicals as Mediators of Inflammation H. Sies, Oxidative Stress 1985 Academic Press London 403 435
2. H. Kühn, J. Belkner, R. Wiesner, and A.R. Brash J. Biol. Chem. 265 1990 18351
3. E. Pontiki, and D. Hadjipavlou-Litina Curr. Enzyme Inhib. 1 2005 309
4. K. Muller Arch. Pharm. 327 1994 3
5. W. Sneader Drug Discovery: A History 2005 John Wiley & Sons West Sussex
6. P. Moutevelis-Minakakis, M. Gianni, H. Stougiannou, P. Zoumpoulakis, A. Zoga, A.D. Vlahakos, E. Iliodromitis, and T. Mavromoustakos Bioorg. Med. Chem. Lett. 13 2003 1737
7. T. Mavromoustakos, P. Moutevelis-Minakakis, C.G. Kokotos, P. Kontogianni, A. Politi, P. Zoumpoulakis, J. Findlay, A. Cox, A. Balmforth, A. Zoga, and E. Iliodromitis Bioorg. Med. Chem. 14 2006 4353
8. E. Srzypczak-Jankum, R.A. Bross, R.T. Carroll, W.R. Dunham, and M.O. Funk Jr. J. Am. Chem. Soc. 123 2001 10814
9. K. Okumura, I. Inoue, M. Ikezaki, G. Hayashi, S. Nurimoto, and K. Shintomi J. Med. Chem. 9 1966 315
10. G. Dannhardt, A. Bauer, and U. Nowe Arch. Pharm. 330 1997 74
11. C. Fotakis, S. Gega, E. Siapi, C. Potamitis, K. Viras, P. Moutevelis-Minakakis, C.G. Kokotos, S. Durdagi, B. Grdadolnik, B. Sartori, M. Rappolt, and T. Mavromoustakos Biochim. Biophys. Acta 1798 2010 422
12. I. Kyrikou, S. Xadjikakou, D. Kovala-Demertzi, K. Viras, and T. Mavromoustakos Chem. Phys. Lipids 132 2004 157
13. J.B. Behr, A. Defoin, J. Pires, J. Streith, L. Macko, and M. Zehnder Tetrahedron 52 1996 3283
14. M. Otsuka, T. Masuda, A. Haupt, M. Ohno, T. Shiraki, Y. Sugiura, and K. Maeda J. Am. Chem. Soc. 112 1990 838
15. J.L. Marco J. Heterocycl. Chem. 23 1986 1062
16. W.R. Roush, and S. Russo-Rodriguez J. Org. Chem. 52 1987 598
17. K. Tamaki, J.B. Shotwell, R.D. White, I. Drutu, T. Petsch, T.V. Nheu, H. He, Y. Hirokawa, H. Maruta, and J.L. Wood Org. Lett. 3 2001 1689
18. T.D. Nelson, and R.D. Crouch Synthesis 9 1996 1031
19. R.N. Salvatore, A.S. Nagle, and K.W. Jung J. Org. Chem. 67 2002 674
20. R.L. Prior, X. Wu, and K. Schaich J. Agric. Food Chem. 53 2005 4290
21. T. Kulicic, A. Radonic, V. Katalinic, and M. Milos Food Chem. 85 2004 633
22. P. Molyneux J. Sci. Technol. 26 2004 211
23. M.S. Blois Nature 181 1958 1199
24. R.B. Taraborewala, and J.M. Kauffman J. Pharm. Sci. 79 1990 173
25. E. Pontiki, and D. Hadjipavlou-Litina Mini-Rev. Med. Chem. 3 2003 487
26. E. Pontiki, and D. Hadjipavlou-Litina Curr. Med. Chem.-Anti-Inflammatory and Anti-Allergy Agents 3 2004 139
27. E. Pontiki, and D. Hadjipavlou-Litina Med. Res. Rev. 28 2008 39
28. A. Detsi, M. Majdalani, A. Kontogiorgis, and D. Hadjipavlou-Litina Bioorg. Med. Chem. 17 2009 8073
29. D. Hadjipavlou-Litina, G.E. Magoulas, M. Krokidis, and D. Papaioannou Eur. J. Med. Chem. 45 2010 298
30. T.Y. Shen Non Steroidal Anti-inflammatory Agents M.E. Wolf, Burger's Medicinal Chemistry 1980 John Wiley and Sons New York 1217 1219
31. L.J. Breña-Valle, C.R. Sánchez, and R. Cruz-Almanza Tetrahedron: Asymmetry 7 1996 1019
32. G.L. Olson, H.-C. Cheung, E. Chiang, V.S. Madison, J. Sepinwall, P. Vincent, A. Winokur, and K.A. Gary J. Med. Chem. 38 1995 2866
33. A. Oeveren, J.F.G.A. Jansen, and B.L. Feringa J. Org. Chem. 59 1994 5999
34. D. Amantini, R. Bellegia, F. Fringuelli, F. Pizzo, and L. Vaccaro J. Org. Chem. 69 2004 2896
35. S.D. Abbott, P. Lane-Bell, K.P.S. Sidhu, and J. Vederas J. Am. Chem. Soc. 116 1994 6513
36. F. Arndt Org. Synth. Coll. Vol. 2 1943 165
37. F. Bellamy, P. Martz, and J. Streith Tetrahedron Lett. 36 1974 3189
38. E. Pontiki, and D. Hadjipavlou-Litina Bioorg. Med. Chem. 15 2007 5819
39. I. Gülcin Toxicology 217 2006 213
40. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans Free Radical Biol. Med. 26 1999 1231
41. W.F. Van Gunsteren, and H.J.C. Berendsen J. Mol. Biol. 176 1984 559
42. W.F. Van Gunsteren, and H.J.C. Berendsen Angew Chem., Int. Ed. Engl. 29 1990 992
43. W. Welch, J. Ruppert, and A.N. Jain Chem. Biol. 3 1996 449
44. J. Ruppert, W. Welch, and A.N. Jain Protein Sci. 6 1997 524
45. A.N. Jain J. Comput. Aided Mol. Des. 10 1996 427
46. Schrödinger Suite 2009 Protein Preparation Wizard; Epik version 2.0, Schrödinger, LLC: New York, 2009.
47. Biobyte Corp., C-QSAR Database, 201 West 4th Str., Suite 204, Claremont CA, CA 91711, USA.