New pentasubstituted pyrrole hybrid atorvastatin-quinoline derivatives with antiplasmodial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 26, Issue 8, 2016, Pages 1881-1884

  Carvalho, Rita C C ^a,b   Martins, Wagner A ^a   Silva, Tayara P ^a   Kaiser, Carlos R ^b   Bastos, Mônica M ^a   Pinheiro, Luiz C S ^a   Krettli, Antoniana U ^a   Boechat, Núbia ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Atorvastatin; Chloroquine; Malaria; Pentasubstituted pyrrole; Primaquine

Indexed keywords

AMINOQUINOLINE DERIVATIVE; ANTIMALARIAL AGENT; ATORVASTATIN; CARBON; CHLOROQUINE; PRIMAQUINE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLINE;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ERYTHROCYTE; HUMAN; HUMAN CELL; NONHUMAN; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SENSITIVITY; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIMALARIALS; ATORVASTATIN CALCIUM; DOSE-RESPONSE RELATIONSHIP, DRUG; MOLECULAR STRUCTURE; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; PYRROLES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84960540490     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2016.03.027     Document Type: Article

References (44)

1. World Health Organization (WHO) Guidelines for the Treatment of Malaria 3rd ed. 2015 available at: Http://apps.who.int/iris/bitstream/10665/162441/1/9789241549127-eng.pdf?ua=1&ua=1 (accessed: August/2015)
2. World Health Organization (WHO) World Malaria Report 2014 available at: Http://www.who.int/malaria/publications/world-malaria-report-2014/report/en/ (accessed: August/2015)
3. G. Pasvol Brit. Med. Bull. 75-76 2005 29
4. V. Bhardwaj, D. Gumber, V. Abbot, S. Dhiman, and P. Sharma RSC Adv. 5 2015 15233
5. V. Estévez, M. Villacampa, and J.C. Menédez Chem. Soc. Rev. 39 2010 4402
6. M. Casagrande, N. Basilico, S. Parapini, S. Romeo, D. Taramelli, and A. Sparatore Bioorg. Med. Chem. 16 2008 6813
7. T. Towle, I. Chang, R.J. Kerns, and P. Bhanot Bioorg. Med. Chem. Lett. 23 2013 1874
8. D. Panchal, and P. Bhanot Antimicrob. Agents Chemother. 54 2010 4269
9. C.A. Diaz, J. Allocco, M.A. Powles, L. Yeung, R.G.K. Donald, J.W. Anderson, and P.A. Liberator Mol. Biochem. Parasitol. 146 2006 78
10. G.H. Posner, M.H. Parker, J. Northrop, J.S. Elias, P. Ploypradith, S. Xie, and T.A. Shapiro J. Med. Chem. 42 1999 300
11. Posner, G. H.; Woo, S. H.; Ploypradith, P.; Parker, M. H.; Shapiro, T. A.; Elias, J. S.; Northrop, J.; Zheng, Q. Y.; Murray, C.; Daughenbaugh, R. J. U.S. Patent 6,160,004, 2000.
12. B. Pradines, M. Torrentino-Madamet, A. Fontaine, M. Henry, E. Baret, J. Mosnier, S. Briolant, T. Fusai, and C. Rogier Antimicrob. Agents Chemother. 51 2007 2654
13. H. Savini, J.B. Souraud, S. Briolant, E. Baret, R. Amalvict, C. Rogier, and B. Pradines Antimicrob. Agents Chemother. 54 2010 966
14. J. Dormoi, S. Briolant, P. Pascual, C. Desgrouas, C. Travaillé, and B. Pradines Malar. J. 12 2013 302
15. E. Profumo, B. Buttari, L. Saso, and R. Riganò Curr. Top. Med. Chem. 14 2014 2542
16. N. Wilson, W. Solomon, L. Anderson, S. Titts, V. Bond, M. Liu, and J. Stiles PLoS One 8 2013 e60898
17. P.A. Reis, V. Estato, T.I. Silva, J.C. d'Avila, L.D. Siqueira, E.F. Assis, P.T. Bozza, F.A. Bozza, E.V. Tibiriça, G.A. Zimmerman, and H.C. Castro-Faria-Neto PLoS Pathog. 8 2012 e1003099
18. Z. Taoufiq, P. Pino, N. N'dilimabaka, I. Arrouss, S. Assi, F. Soubrier, A. Rebollo, and D. Mazier Malar. J. 10 2011
19. V. Parquet, S. Briolant, M. Torrentino-Madamet, M. Henry, L. Almeras, R. Amalvict, E. Baret, T. Fusaï, C. Rogier, and B. Pradines Antimicrob. Agents Chemother. 53 2009 2248
20. J.B. Souraud, S. Briolant, J. Dormoi, J. Mosnier, H. Savini, E. Baret, R. Amalvict, R. Soulard, C. Rogier, and B. Pradines Malar. J. 11 2012 13
21. A.L. Bienvenu, and S. Picot Antimicrob. Agents Chemother. 52 2008 4203
22. J. Dormoi, S. Savini, R. Amalvict, E. Baret, and B. Pradines Malar. J. 13 2012 189
23. J. Penna-Coutinho, W.A. Cortopassi, A.A. Oliveira, T.C.C. França, and A.U. Krettli PLoS One 6 2011 e21237
24. World Health Organization (WHO) Overview of Malaria Treatment 2014 available at: Http://www.who.int/malaria/areas/treatment/overview/en/ (accessed: August/2015)
25. F.W. Muregi, and A. Ishih Drug Dev. Res. 71 2010 20
26. M. Lödige, M.D. Lewis, E.S. Paulsen, H.L. Esch, G. Pradel, L. Lehmann, R. Brun, G. Bringmann, and A.K. Mueller Int. J. Med. Microbiol. 303 2013 539
27. R. Morphy, and Z. Rankovic J. Med. Chem. 48 2005 6523
28. F.P. Varotti, A.A. Andrade, R.C.de Paula, E.M.S. Fagundes, A.L. Valverde, L.M.U. Mayer, J.S. Mendonca, M.V.N. Souza, N. Boechat, and A.U. Krettili Antimicrob. Agents Chemother. 52 2008 3868
29. Boechat, N.; Souza, M. V. N.; Valverde, A. L.; Krettli, A. U. US Patent 8,802,701 B2, 2014.
30. N. Boechat, L.C.S. Pinheiro, T.S. Silva, A.C. Aguiar, A.S. Carvalho, M.M. Bastos, C.C.P. Costa, S. Pinheiro, A.C. Pinto, J.S. Mendonça, K.D.B. Dutra, A.L. Valverde, O.A. Santos-Filho, and A.U. Krettli Molecules 17 2012 8285
31. N. Boechat, M.L.G. Ferreira, L.C.S. Pinheiro, A.M.L. Jesus, M.M.M. Leite, C.C.S. Junior, A.C.C. Aguiar, I.M. de Andrade, and A.U. Krettli Chem. Biol. Drug Des. 84 2014 325
32. L.C.S. Pinheiro, N. Boechat, M.L.G. Ferreira, C.C.S. Junior, A.M.L. Jesus, M.M.M. Leite, N.B. Souza, and A.U. Krettli Bioorg. Med. Chem. 23 2015 5979
33. T.E. Wellems, and C.V. Plowe J. Infect. Dis. 184 2001 770
34. World Health Organization (WHO) Safety of 8-Aminoquinoline Antimalarial Medicines 2014 available at: Http://apps.who.int/iris/bitstream/10665/112735/1/9789241506977-eng.pdf?ua=1 (accessed: Dec/2015)
35. Gudipati, S.; Katram, S.; Komati, S.; Kudavalli, S. J. WO Patent 2,006,039,441 A2, 2006, CA 2582449A1.
36. J.K. Natarajan, J.N. Alumasa, K. Yearick, K.A. Ekoue-Kovi, L.B. Casabianca, A.C. Dios, C. Wolf, and P.D. Roepe J. Med. Chem. 51 2008 3466
37. W. Trager, and J.B. Jensen Science 193 1976 673
38. V.F. Andrade-Neto, M.O. Goulart, J.F. da Silva Filho, M.J. da Silva, M.D.C.F. Pinto, A.V. Pinto, and A.U. Krettli Bioorg. Med. Chem. Lett. 14 2004 1145
39. C. Lambros, and J.P. Vanderberg J. Parasitol. 1979 418
40. M. Smilkstein, J.X. Kelly, P. Wilairat, and M. Riscoe Antimicrob. Agents Chemother. 48 2004 1806
41. A.C.C. Aguiar, R.M. Santos, F.J.B. Figueiredo, W.A. Cortopassi, A.S. Pimentel, T.C.C. França, M.R. Meneghetti, and A.U. Krettli PLoS One 7 2012 e37259
42. E. Borenfreund, and O. Borrero Cell Biol. Toxicol. 1 1984 55
43. S.J. Hocart, H. Liu, H. Deng, D. De, F.M. Krogstad, and D.J. Krogstad Antimicrob. Agents Chemother. 55 2011 2233
44. R.R. Sagyam, P.R. Padi, M.R. Ghanta, and H. Vurimidi J. Heterocycl. Chem. 44 2007 923