Synthesis and antimalarial activity of new heterocyclic hybrids based on chloroquine and thiazolidinone scaffolds

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 15, 2011, Pages 4562-4573

  Rojas Ruiz, Fernando A ^a   García Sánchez, Rory N ^b,c   Estupiñan, Santiago Villabona ^a   Gómez Barrio, Alicia ^b   Torres Amado, Diego F ^a   Pérez Solórzano, Berta Martín ^b   Nogal Ruiz, Juan J ^b   Martínez Fernández, Antonio R ^b   Kouznetsov, Vladimir V ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c UNIVERSIDAD NACIONAL DE LA AMAZONÍA PERUANA   (Peru)

Author keywords

Antimalarial activity; Chloroquine; Heterocyclic hybrids; Synthesis; Thiazolidin 4 ones

Indexed keywords

2 [3,4 (METHYLENDIOXY)PHENYL] 3 [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]ETHYL]THIAZOLIDIN 4 ONE; 3 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 2 (3,4 DIMETHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 2 (3,4,5 TRIMETHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 2 (FURAN 2 YL)THIAZOLIDIN 4 ONE; 3 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 2 (THIOPHEN 2 YL)THIAZOLIDIN 4 ONE; 3 [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]ETHYL] 2 (3 HYDROXY 4 METHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]ETHYL] 2 (4 HYDROXY 3 METHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]ETHYL] 2 PHENYLTHIAZOLIDIN 4 ONE; 3 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 2 (3,4 DIMETHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 2 (FURAN 2 YL)THIAZOLIDIN 4 ONE; 3 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 2 (THIEN 2 YL)THIAZOLIDIN 4 ONE; 3 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PROPYL] 2 (4 HYDROXY 3 METHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PROPYL] 2 PHENYLTHIAZOLIDIN 4 ONE; 3 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] 2 (3,4 DIMETHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] 2 (FURAN 2 YL)THIAZOLIDIN 4 ONE; 3 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] 2 (THIEN 2 YL)THIAZOLIDIN 4 ONE; 3 [4 [(7 CHLOROQUINOLIN 4 YL)AMINO]BUTYL] 2 (4 HYDROXY 3 METHOXYPHENYL)THIAZOLIDIN 4 ONE; 7 CHLORO N (1 PHENYLETHYL)QUINOLIN 4 AMINE; 7 CHLORO N [(4 METHOXYPHENYL)METHYL]QUINOLIN 4 AMINE; ANTIMALARIAL AGENT; CHLOROQUINE; HEMATIN; N BENZYL 7 CHLORQUINOLIN 4 AMINE; N1 (7 CHLOROQUINOLIN 4 YL)BUTANE 1,4 DIAMINE; N1 (7 CHLOROQUINOLIN 4 YL)ETHANE 1,2 DIAMINE; N1 (7 CHLOROQUINOLIN 4 YL)PROPANE 1,3 DIAMINE; THIAZOLE DERIVATIVE; THIAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTALLIZATION; CYTOTOXICITY; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYBRIDIZATION; LIPOPHILICITY; LIVER CELL; LIVER TOXICITY; MELTING POINT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

ANIMALS; ANTIMALARIALS; CELL LINE; CELL SURVIVAL; CHLOROQUINE; DRUG RESISTANCE, MULTIPLE; HEP G2 CELLS; HUMANS; MALARIA, FALCIPARUM; MICE; PLASMODIUM FALCIPARUM; THIAZOLIDINES;

PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

EID: 79960565312     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.025     Document Type: Article

References (22)

1. R.G. Ridley Nature 415 2002 686 693
2. V.V. Kouznetsov, and A. Gómez-Barrio Eur. J. Med. Chem. 44 2009 3091 3113
3. R.G. Ridley Nature 374 1995 269 271
4. A.M. Thayer Chem. Eng. News 83 2005 69 82
5. P.M. O'Neill, B.K. Park, A.E. Shone, J.L. Maggs, P. Roberts, P.A. Stocks, G.A. Biagini, P.G. Bray, P. Gibbons, N. Berry, P.A. Winstanley, A. Mukhtar, R. Bonar-Law, S. Hindley, R.B. Bambal, C.B. Davis, M. Bates, T.K. Hart, S.L. Gresham, R.M. Lawrence, R.A. Brigandi, F.M. Gomez-Delas-Heras, D.V. Gargallo, and S.A. Ward J. Med. Chem. 52 2009 1408 1415
6. B. Meunier Acc. Chem. Res. 41 2008 69 77
7. F. Bellot, F. Coslédan, L. Vendier, J. Brocard, B. Meunier, and A. Robert J. Med. Chem. 53 2010 4103 4109
8. J.J. Walsh, D. Coughlan, N. Heneghan, C. Gaynor, and A. Bell Bioorg. Med. Chem. Lett. 17 2007 3599 3602
9. R.B. Lesyk, and B. Zimenkovsky Curr. Org. Chem. 8 2004 1547 1577
10. Y.S. Prabhakar, V.R. Solomon, M.K. Gupta, and S.B. Katti S.P. Gupta, Topics in Heterocyclic Chemistry 4 2006 Springer Berlin 161 249
11. V.R. Solomon, W. Haq, K. Srivastava, S.K. Puri, and S.B. Katti J. Med. Chem. 50 2007 394 398
12. P.M. O′Neill, A.E. Shone, D. Stanford, G. Nixon, E. Asadollahy, B.K. Park, J.L. Maggs, P. Roberts, P.A. Stocks, G. Biagini, P.G. Bray, J. Davies, N. Berry, C. Hall, K. Rimmer, P.A. Winstanley, S. Hindley, R.B. Bambal, C.B. Davis, M. Bates, S.L. Gresham, R.A. Brigandi, F.M. Gomez-Delas-Heras, D.V. Gargallo, S. Parapini, L. Vivas, H. Lander, D. Taramelli, and S.A. Ward J. Med. Chem. 52 2009 1828 1844
13. P.B. Madrid, A.P. Liou, J.L. DeRisi, and R.K. Guy J. Med. Chem. 49 2006 4535 4543
14. D. De, F.M. Krogstad, L.D. Byers, and D. Krogstad J. Med. Chem. 41 1998 4918
15. P.A. Stocks, K.J. Raynes, P.G. Bray, B.K. Park, P.M. O′Neill, and S.A. Ward J. Med. Chem. 45 2002 4975 4983
16. J.K. Natarajan, J.N. Alumasa, K. Yearick, K.A. Ekoue-Kovi, L.B. Casabianca, A.C. de Dios, C. Wolf, and P.D. Roepe J. Med. Chem. 51 2008 3466 3479
17. H.F. Motiwala, R. Kumar, and A.K. Chakraborti Aust. J. Chem. 60 2007 369 374
18. M. Smilkstein, N. Sriwilaijaroen, J.X. Kelly, P. Wilairat, and M. Riscoe Antimicrob. Agents Chemother. 48 2004 1803 1806
19. W. Trager, and J. Jensen Science 193 1976 673 675
20. Y. Hattori, and N. Nakanishi Cell. Immunology 165 1995 7 11
21. E. Deharo, R.N. García, P. Oporto, A. Gimenez, M. Sauvain, V. Jullian, and H. Ginsburg Exp. Parasitology 100 2002 252 256
22. W. Peters Chemotherapy and drug resistance in malaria second ed. 1987 Academic Press London