Morita-Baylis-Hillman adducts: Biological activities and potentialities to the discovery of new cheaper drugs

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 13, 2012, Pages 3954-3971

  Lima Junior, Claudio G ^a   Vasconcellos, Mário L A A ^a  

^a FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

Author keywords

Antibiotics; Biological activities; Cancer; Herbicides; Morita Baylis Hillman adducts; Negligenced disease

Indexed keywords

2 [(2,4 DICHLOROPHENYL)(HYDROXY)]METHYLACRYLATE; 3 [HYDROXY (4 NITROPHENYL)METHYL]BUT 3 EN 2 ONE; ANTHELMINTIC AGENT; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTILEISHMANIAL AGENT; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; ANTIPARASITIC AGENT; BENZNIDAZOLE; CHLORAMPHENICOL; CHLOROQUINE; HERBICIDE; MONOACYLGLYCEROL; NEW DRUG; NYSTATIN; RISEDRONIC ACID; UNCLASSIFIED DRUG;

ANTHELMINTIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ASPERGILLUS NIGER; BAYLIS HILLMAN REACTION; BIOLOGICAL ACTIVITY; BIOMPHALARIA GLABRATA; CANDIDA ALBICANS; CORYNEBACTERIUM DIPHTHERIAE; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; EPIMASTIGOTE; ESCHERICHIA COLI; HERBICIDAL ACTIVITY; HUMAN; HYDROGENATION; KLEBSIELLA PNEUMONIAE; LEISHMANIA; LEISHMANIA CHAGASI; LIPOPHILICITY; MASS SPECTROMETRY; MICHAEL ADDITION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR HYBRIDIZATION; NONHUMAN; ONE POT SYNTHESIS; OXYGENATION; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; REVIEW; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE;

ANIMALS; ANTIPARASITIC AGENTS; GREEN CHEMISTRY TECHNOLOGY; HUMANS; LEISHMANIA; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA CRUZI;

BIOMPHALARIA GLABRATA; GASTROPODA; LEISHMANIA AMAZONENSIS; LEISHMANIA DONOVANI CHAGASI; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; TRYPANOSOMA CRUZI;

EID: 84862223585     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.04.061     Document Type: Review

References (73)

1. K. Morita, Z. Suzuki, and H. Hirose Bull. Chem. Soc. Jpn. 41 1968 2815
2. Baylis, A. B.; Hillman, M. E. D. U.S. Patent 3,743,669, 1973;
3. Chem. Abstr. 1972, 77, 34174q.
4. D. Basavaiah, A.J. Rao, and T.T. Satyanarayana Chem. Rev. 103 2003 811
5. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447
6. K.E. Price, S.J. Broadwater, H.M. Jung, and D.T. McQuade Org. Lett. 7 2005 147
7. R. Robiette, V.K. Aggarwal, and J.N. Harvey J. Am. Chem. Soc. 129 2007 15513
8. G.W. Amarante, H.M.S. Milagre, B.G. Vaz, B.R.V. Ferreira, M.C. Eberlin, and F. Coelho J. Org. Chem. 74 2009 3031
9. D. Cantillo, and C.O. Kappe J. Org. Chem. 75 2010 8615
10. C.G.L. Junior, F.P.L. Silva, R.G. de Oliveira, F.L. Subrinho, and M.L.A.A. Vasconcellos J. Braz. Chem Soc. 22 2011 2220
11. M. Shi, F. Wang, M.-X. Zhao, and Y. Wei Chemistry of the Morita-Baylis-Hillman Reaction 2011 Royal Society of Chemistry Cambridge, UK
12. S.E. Drewes, and N.D. Emslie J. Chem. Soc., Perkin Trans. 1 9 1982 2079
13. H.M.R. Hoffmann, and J. Rabe Angew. Chem., Int. Edit. 95 1983 795
14. A. Patra, S. Batra, A.P. Bhaduri, A. Khanna, R. Chander, and M. Dikshit Bioorg. Med. Chem. 11 2003 2269
15. R. Sreevani, A. Manjula, and B.V. Rao J. Heterocycl. Chem. 48 2011 586
16. P. Narender, U. Srinivas, M. Ravinder, A. Rao, Ch. Rames, K. Harakishore, B. Gangadasu, U.S.N. Murthy, and J. Rao Bioorg. Med. Chem. 14 2006 4600
17. Ryu, D. H.; Hwang, G. S.; Kim, K. H.; Park, J. H.; Kim, H. J. Int. Patent 110655 A1, 2009.
18. J. Kaur, P. Kumar, S. Tyagi, R. Pathak, S. Batra, P. Singh, and N. Singh Antimicrob. Agents Chemother. 55 2011 659
19. B. Das, N. Choowdhury, K. Damodar, and J. Banerjee Chem. Pharm. Bull. 55 2007 1725
20. M.K. Kundu, N. Sundar, S.K. Kumar, S.V. Bhat, S. Biswas, and N. Valecha Bioorg. Med. Chem. Lett. 9 1999 731
21. P. Narender, U. Srinivas, B. Gangadasu, S. Biswas, and V.J. Rao Bioorg. Med. Chem. Lett. 15 2005 5378
22. 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
23. L.K. Kohn, C.H. Pavam, D. Veronese, F. Coelho, J.E. de Carvalho, and W.P. Almeida Eur. J. Med. Chem. 41 2006 738
24. T.J. Ritchie, and S.J.F. Macdonald Drug Discovery Today 14 2009 1011
25. R. Mohan, N. Rantogi, I.N.N. Namboothiri, S.N. Mobin, and D. Panda Bioorg. Med. Chem. 14 2006 8073
26. N. Rastog, R. Mohan, D. Panda, S.M. Mobin, and I.N.N. Namboothiri Org. Biomol. Chem. 4 2006 3211
27. M. Dadwal, R. Mohan, D. Panda, S.M. Mobin, and I.N.N. Namboothiri Chem. Commun. 2006 338
28. I. Rozas, R. Carrasco, and Z.J. Kunakbaeva Mol. Struct. (Theochem.) 626 2003 209
29. L.R. Berube, S. Farah, R.A. McClelland, and A.M. Rauth Int. J. Radiat. Oncol. Biol. Phys. 22 1992 817
30. O.W. Griffith, and A. Meister J. Biol. Chem. 254 1979 7558
31. J.M. Williamson, B. Boettcher, and A. Meister Proc. Natl. Acad. Sci. 79 1982 6246
32. A. Russo, W. Degraff, N. Friedman, and J.B. Mitchell Cancer Res. 46 1986 2845
33. K.D. Tew Cancer Res. 54 1994 4313
34. G. Powis, J.R. Gasdaka, and A. Baker Adv. Pharmacol. 38 1997 329
35. M.O.F. Goulart, A.A. de Souza, F.C. de Abreu, F.S. de Paula, E.M. Sales, W.P. Almeida, O. Buriez, and C. Amatore J. Electrochem. Soc. 154 2007 121
36. C.R. Yu, L.H. Xu, S. Tu, Z.N. Li, and B. Li J. Fluorine Chem. 127 2006 1540
37. G.-Q. Yang, C.-R. Yu, X.-L. Yu, and X.-H. Qiu Huaxue Shiji 33 2011 803
38. 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
39. 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
40. 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
41. A.L. Edinger, and C.B. Thompson Curr. Opin. Cell Biol. 16 2004 663
42. L.T.D. Tonin, V.A. Barbosa, C.C. Bocca, E.R.F. Ramos, C.V. Nakamura, W.F. da Costa, E.A. Basso, T.U. Nakamura, and N.H. Sarragiotto Eur. J. Med. Chem. 44 2009 1745
43. D. Perez-Sala Front. Biosci. 12 2007 4456
44. J.A. Urbina, J.L. Concepcion, S. Rangel, G. Visbal, and R. Lira Mol. Biochem. Parasitol. 125 2002 35
45. J.A. Urbina Parasitology 114 1997 S91
46. M.A. La-Scalea, S.H.P. Serrano, E.I. Ferreira, and A.M. Oliveira Brett J. Pharm. Biomed. Anal. 29 2002 561
47. C.G.L. Junior, P.A.C. de Assis, F.P.L. Silva, S.C.O. Sousa, N.G. 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
48. F.E.B. Alencar, 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. 499 2007 336
49. L.M. Lima, and E.J. Barreiro Curr. Med. Chem. 12 2005 23
50. C. Viegas-Junior, A. Danuello, V.S. Bolzani, E.J. Barreiro, and C.A.M. Fraga Curr. Med. Chem. 14 2007 1829
51. F.P.L. Silva, P.A.C. de Assis, C.G.L. Junior, N.G. de Andrade, S.M.D. da Cunha, M.R. Oliveira, and M.L.A.A. Vasconcellos Eur. J. Med. Chem. 46 2011 4295
52. T.P. Barbosa, S.C.O. Sousa, F.M. Amorim, Y.K.S. Rodrigues, P.A.C. de Assis, J.P.A. Caldas, M.R. Oliveira, and M.L.A.A. Vasconcellos Bioorg. Med. Chem. 19 2011 4250
53. F.R. Paula, S.H.P. Serrano, and L.C. Tavares Quim. Nova 32 2009 1013
54. F.C. De Abreu, P.A.L. Ferraz, and M.O.F. Goulart J. Braz. Chem. Soc. 13 2002 19
55. J.A. Squella, S. Bollo, and L.J. Núñez-Vergara Curr. Org. Chem. 9 2005 565
56. M.D. da S. Julião, E.I. Ferreira, N.G. Ferreira, and S.H.P. Serrano Electrochim. Acta 51 2006 5080
57. J.H. Tocher, and D.I. Edwards Biochem. Pharmacol. 50 1995 1367
58. S. Bollo, S. Gunckel, L.J. Nunez-Vergara, L.J. Chauviere, G. Chauviere, and J.A. Squella Electroanalysis 17 2005 134
59. Y.G. de Paiva, A.A. de Souza, C.G. Lima-Junior, F.P.L. Silva, E.B.A. Filho, C.C. Vasconcelos, F.C. de Abreu, O.F. Goulart Marília, and M.L.A.A. Vasconcellos J. Braz. Chem. Soc. 23 2012 894
60. F.R. Paula, G.H.G. Trossini, E.I. Ferreira, S.H.P. Serrano, C.M.S. Menezes, and L. Tavares J. Braz. Chem. Soc. 21 2010 740
61. E. Srihari, G.S. Kumar, C.N.S.S.P. Kumar, R.K. Seth, S. Biswas, B. Sridhar, and V.J. Rao Heterocycl. Commun. 17 2011 111
62. S.V. Bhat, and S.A. Singh Acta Pharm. 62 2011 447
63. S.C.O. Sousa, C.G. Lima-Junior, F.P.L. Silva, N.G. Andrade, T.P. Barbosa, and M.L.A.A. Vasconcellos J. Braz. Chem. Soc. 22 2011 1634
64. M.J. Almela, P.A. Torres, S. Lozano, and E. Herreros Toxicol. In vitro 23 2009 1528
65. J.E. Charris, G.M. Lobo, J. Camacho, R. Ferrer, A. Barazarte, J.N. Domínguez, N. Gamboa, J.R. Rodrigues, and J.E. Angel Lett. Drug Des. Discov. 4 2007 49
66. M.A. El-Apasery, S.M. Al-Mousawi, and M.H. Elnagdi Eur. J. Chem. 2 2011 168
67. J. Gálvez, M. Gálvez-Llompart, and R. García- Domenech Expert Opin. Drug Discov. 7 2012 133
68. FDA's policy statement for the development of new stereoisomeric drugs. http://www.fda.gov/cder/guidance/stereo.html.
69. N. Hayashi, K. Yanagihara, and S. Tsuboi Tetrahedron: Asymmetry 9 1998 3825
70. A.Z. Walton, W.C. Conerly, Y. Pompeu, B. Sullivan, and J.D. Stewart ACS Catal. 1 2011 989
71. L.C. Ramírez, A.N. Manjarrez, M.H.I. Pérez, O.A. Solís, H. Luna, and J. Cassani Rev. Mex. Cienc. Farm. 4 2009 5
72. G.V.M. Sharma, and P.R. Krishna Mini-Rev. Org. Chem. 3 2006 137
73. R.O.M.A. de Souza, J.C. Barros, O.A.C. Antunes, and J.F.M. da Silva Z Naturforsch. [C] - J. Biosci. 66 2011 136