Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita-Baylis-Hillman adducts

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 4295-4301

  Silva, Fábio P L ^a   De Assis, Priscilla A C ^a   Junior, Claudio G L ^a   De Andrade, Natália G ^a   Da Cunha, Saraghina M D ^a   Oliveira, Márcia R ^a   Vasconcellos, Mário L A A ^a  

^a FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

Author keywords

Bioisoterism; Leishmania amazonensis; Leishmaniasis; Lipophilicity; Molecular modification strategy; Morita Baylis Hillman adducts

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; 2 [HYDROXY(2 NITROPHENYL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(2 NITROPHENYL)PROPYL]PROPANOATE; 2 [HYDROXY(3 NITROPHENYL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(3 NITROPHENYL)PROPYL]PROPANOATE; 2 [HYDROXY(4 BROMOPHENYL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(4 BROMOPHENYL)PROPYL]PROPANOATE; 2 [HYDROXY(4 NITROPHENYL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(4 NITROPHENYL)PROPYL]PROPANOATE; 2 [HYDROXY(NAPHTH 2 YL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(NAPHTH 2 YL)PROPYL]PROPANOATE; 2 [HYDROXY(PYRIDIN 2 YL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(PYRIDIN 2 YL)PROPYL]PROPANOATE; 2 [HYDROXY(PYRIDIN 3 YL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(PYRIDIN 3 YL)PROPYL]PROPANOATE; 2 [HYDROXY(PYRIDIN 4 YL)HYDROXYETHYL]PROPANOATE; 2 [HYDROXY(PYRIDIN 4 YL)PROPYL]PROPANOATE; ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ANTIPROTOZOAL AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; BAYLIS HILLMAN REACTION; CYTOTOXICITY TEST; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; IC 50; LEISHMANIA; MACROPHAGE; MOUSE; NONHUMAN; ONE POT SYNTHESIS;

ANIMALS; ANTIPROTOZOAL AGENTS; CELLS, CULTURED; INHIBITORY CONCENTRATION 50; LEISHMANIA; MACROPHAGES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICE; SPECTROPHOTOMETRY, INFRARED;

EID: 80052915855     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.06.036     Document Type: Article

References (59)

1. N. Feasey, M.W. Jones, D.C.W. Mabey, and A.W. Solomon Br. Med. Bull. 93 2010 179 200
2. A. Cavalli, and M.L. Bolognesi J. Med. Chem. 52 2009 7339 7359
3. E.R. Sharlow, D. Close, T. Shun, S. Leimgruber, R. Reed, G. Mustata, P. Wipf1, J. Johnson, M. O'Neil, M. Grögl, A.J. Magill, and J.S. Lazo PLoS. Negl. Trop. Dis. 3 2009 e540
4. P. Mitropoulos, P. Konidas, and M. Durkin-Konidas J. Am. Acad. Dermatol. 63 2010 309 322
5. M. Calvopina, A.G. Guevara, R.X. Armijos, Y. Hashiguchi, R.N. Davidson, and P.J. Cooper Intern. J. Dermatol. 43 2004 659 663
6. R.F.Q. Grenfell, E.A. Marques-da-Silva, M.C. Souza-Testasicca, E.A.F. Coelho, A.P. Fernandes, L.C.C. Afonso, and S.A. Rezende Mem. Inst. Oswaldo Cruz 105 2010 818 822
7. R. Reithinger PloS Negl. Trop. Dis. 2 2008 e285
8. R. Lainson, and J.J. Shaw New world leishmaniasis. The neotropical leishmania species L. Collier, A. Balows, M. Sussmann, H. Arnold, Microbiology and Microbial Infectious Diseases ninth ed 1998 Topley & Wilson's London 241 266
9. J. Mishra, A. Saxena, and S. Singh Curr. Med. Chem. 14 2007 1153 1169
10. J.D. Berman Clin. Infect. Dis. 24 1997 684 703
11. S. Noazina, F. Modabberb, A. Khamesipourc, P.G. Smithd, L.H. Moultone, K. Nasserif, I. Sharifig, E.A.G. Khalilh, I.D.V. Bernali, C.M.F. Antunes, M.P. Kienya, and M. Tannerk Vaccine 26 2008 6759 6767
12. K. Morita, Z. Suzuki, and H. Hirose Bull. Chem. Soc. Jap 41 1968 2815
13. A.B. Baylis, and M.E.D. Hillman Chem. Abstr. 77 1972 34174q1, German Patent 2155113
14. F.A.S. Coelho, and W.P. Almeida Quím. Nova 23 2000 98 101
15. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 892
16. V. Singh, and S. Batra Tetrahedron 64 2008 4511 4574
17. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447 5674
18. R.O.M.A. de Souza, and L.S.M. Miranda Mini-Rev. Org. Chem. 7 2010 212 220
19. F. Coelho, W.P. Almeida, D. Veronese, C.R. Mateus, L.E.C. Silva, R.C. Rossi, G.P. Silveira, and C.H. Pavam Tetrahedron 58 2002 7437 7447
20. J.S. Hill, and N.S. Isaacs Tetrahedron Lett. 27 1986 5007 5010
21. R.O.M.A. de Souza, P.H. Fregadoli, K.M. Gonalves, L.C. Sequeira, V.L.P. Pereira, L.C. Filho, P.M. Esteves, M.L.A.A. Vasconcellos, and O.A.C. Antunes Lett. Org. Chem. 3 2006 936 939
22. S. Rafel, and J.W. Leahy J. Org. Chem. 62 1997 1521 1522
23. R.O.M.A. de Souza, B.A. Meireles, L.C.S. Aguiar, and M.L.A.A. Vasconcellos Synthesis 2004 1595 1600
24. M.K. Kundu, N. Sundar, S.K. Kumar, S.V. Bhat, S. Biswas, and N. Valecha Bioorg. Med. Chem. Lett. 9 1999 731 736
25. P. Narender, U. Srinivas, B. Gangadasu, S. Biswas, and R.V. Jayathirtha Bioorg. Med. Chem. Lett. 15 2005 5378 5381
26. M.L.A.A. Vasconcellos, T.M.S. Silva, C.A. Camara, R.M. Martins, K.M. Lacerda, H.M. Lopes, V.L.P. Pereira, R.O.M.A. de Souza, and L.T.C. Crespo Pest Manag. Sci. 62 2006 288 292
27. L.K. Kohn, C.H. Pavam, D. Veronense, F. Coelho, J.E. De Carvalho, and W.P. Almeida Eur. J. Med. Chem. 41 2006 738 744
28. R.O.M.A. de Souza, V.L.P. Pereira, M.F. Muzitano, B. Rossi-Bergmann, E.B.A. Filho, and M.L.A.A. Vasconcellos Eur. J. Med. Chem. 42 2007 99 102
29. T.C. Barbosa, C.G.L. Junior, F.P.L. Silva, H.M. Lopes, L.R.F. Figueiredo, S.C.O. Souza, G.N. Batista, T.G. Silva, T.M. Silva, M.R. Oliveira, and M.L.A.A. Vasconcellos Eur. J. Med. Chem. 44 2009 1726 1730
30. J.M. Sandes, A.R. Borges, C.G.L. Junior, F.P.L. Silva, G.A.U. Carvalho, G.B. Rocha, M.L.A.A. Vasconcellos, and R.C.B.Q. Figueiredo Bioorg. Chem. 38 2010 190 195
31. C.G.L. Junior, P.A.C. de Assis, F.P.L. Silva, S.C.O. Sousa, N.G. de Andrade, T.P. Barbosa, P.L.N. Nerís, L.V.G. Segundo, I.C. Anjos, G.A.U. Carvalho, G.B. Rocha, M.R. Oliveira, and M.L.A.A. Vasconcellos Bioorg. Chem. 38 2010 279 284
32. L.S.M. Miranda, B.G. Marinho, S.G. Leitão, E.M. Matheus, P.D. Fernandes, and M.L.A.A. Vasconcellos Bioorg. Med. Chem. Lett. 14 2004 1573 1575
33. L.S.M. Miranda, B.A. Meireles, J.S. Costa, V.L.P. Pereira, and M.L.A.A. Vasconcellos Synlett 2005 869 871
34. K.G. Alencar, F. Dumas, P.R.R. Costa, and M.L.A.A. Vasconcellos Tetrahedron: Asymmetry 8 1997 579 583
35. H.C.A. Filho, U.F.L. Filho, S. Pinheiro, M.L.A.A. Vasconcellos, and P.R.R. Costa Tetrahedron: Asymmetry 5 1994 1219 1220
36. M.L.A.A. Vasconcellos, D. Desmaële, P.R.R. Costa, and J. d'Angelo Tetrahedron Lett. 33 1992 4921 4922
37. A.L. Coelho, M.L.A.A. Vasconcellos, A.B.C. Simas, J.A. Rabi, and P.R.R. Costa Synthesis 1992 914 916
38. R.O.M.A. de Souza, V.L.P. Pereira, P.M. Esteves, and M.L.A.A. Vasconcellos Tetrahedron Lett. 49 2008 5902 5905
39. R.O.M.A. de Souza, A.L.F. Souza, T.L. Fernandez, A.C. Silva, V.L.P. Pereira, P.M. Esteves, M.L.A.A. Vasconcellos, and O.A.C. Antunes Lett. Org. Chem. 5 2008 379 382
40. R.O.M.A. de Souza, and M.L.A.A. Vasconcellos Catal. Commun. 5 2004 21 24
41. R.O.M.A. de Souza, and M.L.A.A. Vasconcellos Synth. Commun. 33 2003 1393 1399
42. L.M. Lima, and E.J. Barreiro Cur. Med. Chem. 12 2005 23 49
43. R.A. Scherrer, and S.M. Howard J. Med. Chem. 20 1977 53 58
44. K. Valkó J. Chromatogr. A 1037 2004 299 310
45. P.R. Andrews, D.J. Craik, and J.L. Martin J. Med. Chem. 27 1984 1648 1657
46. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 23 1997 3 25
47. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv. Drug Deliv. Rev. 46 2001 3 26
48. T. P. Belova, N. A. Khorkina, A. P. Andronova, S. G. Rozman, T. A. Baiburdov, S. V. Shapovalov, A. A. Khorkin, RU Patent 2005/2259399.
49. H.-B. Sun, R. Hua, and Y. Yin Molecules 11 2006 263 271
50. K.E. Price, S.J. Broadwater, B.J. Walker, and D.T. McQuade J. Org. Chem. 70 2005 3980 3987
51. R. Robiette, V.K. Aggarwal, and J.N. Harvey J. Am. Chem. Soc. 129 2007 5513 15525
52. G.W. Amarante, H.M.S. Milagre, B.G. Vaz, F. Vilacha, R. Bruno, M.N. Eberlin, and F. Coelho J. Org. Chem. 74 2009 3031 3037
53. R. Bade, H.-F. Chan, and J. Reynisson Eur. J. Med. Chem. 45 2010 5646 5652
54. E.B.A. Filho, E. Ventura, S.A. do Monte, B.G. Oliveira, C.G.L. Junior, G.B. Rocha, and M.L.A.A. Vasconcellos Chem. Phys. Lett. 449 2007 336 340
55. L.T.D. Tonin, V.A. Barbosa, C.C. Bocca, E.R.F. Ramos, C.V. Nakamura, W.F. Costa, E.A. Basso, T.U. Nakamura, and M.H. Sarragiotto Eur. J. Med. Chem. 44 2009 1745 1750
56. D.B. Castro-Pinto, E.L. Lima, A.S. Cunha, M. Genestra, R.M. De Léo, F. Monteiro, and L.L. Leon J. Enzym. Inhib. Med. Chem. 22 2007 71 75
57. S.K. Venkatesan, A.K. Shukla, and V.K. Dubey J. Comput. Chem. 31 2010 2463 2475
58. Y. Wei, and M. Shi Acc. Chem. Res. 43 2009 1005 1018
59. T. Mosmann J. Immunol. Methods 65 1983 55 63