Synthesis and antitumoral evaluation of 7-chloro-4-quinolinylhydrazones derivatives

Medicinal Chemistry

Volumn 7, Issue 6, 2011, Pages 599-604

  Montenegro, Raquel Carvalho ^d   Lotufo, Letícia Veras ^c   De Moraes, Manoel Odorico ^c   Do Ópessoa, Cláudia ^c   Rodrigues, Felipe Augusto Rocha ^c   De Lima Ferreira Bispo, Marcelle ^a,b   De Faria Cardoso, Laura Nogueira ^a   Kaiser, Carlos Roland ^b   De Souzaa, Marcus Vinícius Nora ^a,e  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^c FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^d FEDERAL UNIVERSITY OF PARÁ   (Brazil)

^e Rua Sizenando Nabuco   (Brazil)

Author keywords

Antitumoral activity; Cancer; Chloroquine; Drugs; Hydrazones; Quinoline

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 7 CHLORO 4 QUINOLINYLHYDRAZONE DERIVATIVE; ANTINEOPLASTIC AGENT; BENZENE; BROMINE; CHLORINE DERIVATIVE; FLUORINE; HYDRAZONE DERIVATIVE; NITRO DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; PRIORITY JOURNAL; QUANTUM YIELD; STRUCTURE ACTIVITY RELATION;

EID: 80755125963     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340611797928299     Document Type: Article

References (28)

1. Evans, B.E.; Rittle, K.E.; Bock, M.G.; DiPardo, R.M.; Freidinger, R.M.; Whitter, W.L.; Lundell, G.F.; Veber, D.F.; Anderson, P.S.; Chang, R.S.L.; Lotti, V.J.; Cerino, D.J.; Chen, T.B.; Kling, P.J.; Kunkel, K.A.; Springer, J.P.; Hirshfield, J. Methods for drug discovery: Development of potent, selective, orally effective cholecystokinin antagonists. J. Med. Chem., 1988, 31(12), 2235-2246. (Pubitemid 19001640)
2. Patchett, A.A.; Nargund, R.P. Privileged structures-An update. Annu. Rep. Med. Chem., 2000, 35(26), 289-298.
3. M Font, M.; Monge, A.; Ruiz, I.; Heras, B. Structure-activity relationships in quinoline reissert derivatives with HIV-1 reverse transcriptase inhibitory activity. Drug Design Discov. 1997, 14(4), 259-272. (Pubitemid 27234611)
4. Kaminsky, D.; Meltzer, R. I. Quinoline antibacterial agents. Oxolinic acid and related compounds. J. Med. Chem. 1968, 11(1), 160-163.
5. Musiol, R.; Jampilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podeszwa, B.; Palka, A.; Majerz-Maniecka, K.; Oleksyn, B.; Polanski, J. Antifungal properties of new series of quinoline derivatives. Bioorg. Med. Chem. 2006, 14 (10), 3592-3598.
6. Warshakoon, N.C.; Sheville, J.; Bhatt, R.T.; Ji, W.; Mendez-Andino, J.L.; Meyers, K.M.; Kim, N.; Wos, J.A.; Mitchell, C.; Paris, J.L.; Pinney, B.B.; Reizes, O.; Hu, X.E.Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents. Bioorg. Med. Chem. Lett. 2006, 16 (19), 5207-5211. (Pubitemid 44247686)
7. Sloboda, A.E.; Powell, D.; Poletto, J.F.; Pickett, W.C.; Gibbons Jr.; J.J.; Bell, D.H.; Oronsky, A.L.; Kerwar, S.S. Antiinflammatory and antiarthritic properties of a substituted quinoline carboxylic acid: CL 306,293. J. Rheumatol. 1991, 18(6), 855-860.
8. Nakamura, T.; Oka, M.; Aizawa, K.; Soda, H.; Fukuda, M.; Terashi, K.; Ikeda, K.; Mizuta, Y.; Noguchi, Y.; Kimura, Y.; Tsuruo, T.; Kohno, S.Direct interaction between a quinoline derivative, MS-209, and multidrug resistance protein (MRP) in human gastric cancer cells. Biochem. Bioph. Res. Co. 1999, 255(3), 618-624. (Pubitemid 29294848)
9. Solomon, V.R.; Lee, H. Chloroquine and its analogs: A new promise of an old drug for effective and safe cancer therapies.Eur J Pharmacol 2009, 625(1-3), 220-233.
10. Augustijns, P.; Geusens, P.; Verbeke, N. Chloroquine levels in blood during chronic treatment of patients with rheumatoid arthritis. Eur. J. Clin. Pharmacol. 1992, 42(4), 429-433.
11. Savarino, A.; Di Trani, L.; Donatelli, I.; Cauda, R.; Cassone, A. New insights into the antiviral effects of chloroquine. Lancet Infect. Dis. 2006, 6(2), 67-69. (Pubitemid 43138901)
12. Chuandong, F.; Wang, W.; Zhao, B.; Zhanga, S.; Miaoa, J. Chloroquine inhibits cell growth and induces cell death in A549 lung cancer cells. Bioorg. Med. Chem. 2006, 14(9), 3218-3222.
13. Kim, E.L.; Wüstenberg, R.; Rübsam, A.; Schmitz-Salue, C.; Warnecke, G.; Bücker, E.-M.; Pettkus, N.; Speidel, D.; Rohde, V.; Schulz-Schaeffer, W.; Deppert, W.; Giese, A. Chloroquine activates the p53 pathway and induces apoptosis in human glioma cells. Neuro Oncol. 2010, 12(4), 389-400.
14. Candéa, A.L.P.; Ferreira, M.d.L.; Pais, K.C.; Cardoso, L.N.d.F.; Kaiser, C.R.; Henriques, M.d.G.M.d.O.; Lourenço, M.C.S.; Bezerra, F.A.F.M.; de Souza, M.V.N. Synthesis and antitubercular activity of 7-chloro-4-quinolinylhydrazones derivatives. Bioorg. Med. Chem. Lett. 2009, 19(22), 6272-6274.
15. de Souza, M. V. N.; Howie, R. A.; Tiekink, E. R. T.; Wardell, J. L.; Wardell, S. M. S. V. 7-Chloro-4-[(E)-N'-(4-fluorobenzylidene)hydrazinyl] quinoline monohydrate. Acta Crystallogr. E, 2010, 66, 152-153.
16. Souza, M.V.N.D.; Howie, R.A.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.; Kaiser, C.R. 7-Chloro-4-[(E)-2-(2-methoxybenzylidene)hydrazin-1-yl] quinoline monohydrate. Acta Crystallogr. E, 2010, 66(3), 698-699.
17. De Lima Ferreira, M.; Souza, M.V.N.D.; Howie, R.A.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V. 7-Chloro-4-[(E)-2-(4-methoxybenzylidene) hydrazin1yl]quinoline monohydrate. Acta Crystallogr. E, 2010, 66(3), 696-697.
18. Howie, R.A.; de Souza, M.V.N.; Ferreira, M.L.; Kaiser, C.R.; Wardell, J.L.; Wardell, S.M.S.V. Structures of arylaldehyde 7-chloroquinoline-4- hydrazones:supramolecular arrangements derived from N-H⋯N, C-H⋯X (X = N, O, or π) and π⋯π interactions. Z. Kristallogr, 2010, 225(10), 440-447.
19. Howie, R.A.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.; de Souza, M.V.N. 7-Chloro-4-[(E)-(3-chlorobenzylidene)hydrazinyl]-14-quinolinium 3-chlorobenzoate. Acta Crystallogr. E, 2009, 65(12), 3204-3205.
20. Chaston, T.B.; Watts, R.N.; Yuan, J.; Richardson, D.R. Potent antitumor activity of novel iron chelators derived from di-2-pyridylketone isonicotinoyl hydrazone involves fenton-derived free radical generation. Clin. Cancer Res., 2004, 10(21), 7365-7374. (Pubitemid 39487726)
21. Hyap, H.Y.; Yap, B.S.; Blumenschein, G.R. Bisantrene, an active new drug in the treatment.Cancer Res. 1983, 43, 1402-1404.
22. Pellerano, C.; Savini, L.; Fiorini, I. Hydrazinoquinoline derivatives: Antimicrobial and antifungal 4-quinolinehydrazones. Atti Accad. Fisiocritic Siena, 1976, 8(14), 43-57.
23. El-Behery, M.; El-Twigry, H. Synthesis, magnetic, spectral, and antimicrobial studies of Cu(II), Ni(II) Co(II), Fe(III), and UO2(II) complexes of a new Schiff base hydrazone derived from 7-chloro-4-hydrazinoquinoline. Spectrochim Acta A 2007, 66(1), 28-36. (Pubitemid 44834489)
24. Thomas, J.; Berkoff, C.E.; Flagg, W.B.; Gallo, J.J.; Haff, R.F.; Pinto, C.A.; Pellerano, C.; Savini, L. Antiviral quinolinehydrazones. A modified Free-Wilson analysis.J. Med. Chem. 1975, 18(3), 245-250.
25. Al-Sha'alan, N.H. Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a Schiff base hydrazone containing a quinoline moiety.Molecules 2007, 12(5), 1080-1091.
26. Ahmed, S.A.; Gogal Jr.; R.M.; Walsh, J.E. A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes: An alternative to [3H]thymidine incorporation assay. J. Immunol. Methods, 1994, 170(2), 211-224. (Pubitemid 24122510)
27. Sharma, P.; Sharma, J.D. In vitro hemolysis of human erythrocytes-By plant extracts with antiplasmodial activity. J. Ethnopharmacol., 2001, 74(3), 239-243. (Pubitemid 32215453)
28. Krause, W.; Jordan, A.; Scholz, R.; Jimenez, J.-L.M. Iodinated nitroimidazoles as radiosensitizers. Anticancer Res., 2005, 25(3 B), 2145-2151. (Pubitemid 40904616)