1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl)methylene] hydrazine: A potent compound against cancer

Medicinal Chemistry Research

Volumn 21, Issue 11, 2012, Pages 3615-3619

  Montenegro, Raquel Carvalho ^a   Lotufo, Letícia Veras ^d   De Moraes, Manoel Odorico ^b   Pessoa, Claudia DoO ^d   Rodrigues, Felipe Augusto Rocha ^b,d   De Lima Ferreira Bispo, Marcelle ^c   De Alcantara, Camila Cataldi ^a   Kaiser, Carlos Roland ^c   De Souza, Marcus Vinícius Nora ^a  

^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)

Author keywords

Antitumor activity; Cancer; Chloroquine; Drugs; Hydrazones; Quinoline

Indexed keywords

1 (7 CHLOROQUINOLIN 4 YL) 2 [(1H PYRROL 2 YL)METHYLENE]HYDRAZINE; 1 (7 CHLOROQUINOLIN 4 YL) 2 [(5 NITRO FURAN 2 YL)METHYLENE]HYDRAZINE; 1 (7 CHLOROQUINOLIN 4 YL) 2 [(5 NITRO THIOPHEN 2 YL)METHYLENE]HYDRAZINE; ANTINEOPLASTIC AGENT; DOXORUBICIN; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; HUMAN; HUMAN CELL; IC 50; MELANOMA CELL; MEMBRANE DAMAGE; MOLECULAR HYBRIDIZATION; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION;

EID: 84871417617     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9894-8     Document Type: Article

References (16)

1. Ahmed SA, Gogal RM Jr, Walsh JE (1994) 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 170:211-224
2. Augustijns P, Geusens P, Verbeke N (1992) Chloroquine levels in blood during chronic treatment of patients with rheumatoid arthritis. Eur J Clin Pharmacol 42:429-433
3. Chuandong F, Wang W, Zhao B, Zhang S, Miao J (2006) Chloroquine inhibits cell growth and induces cell death inA549 lung cancer cells. Bioorg Med Chem 14:3218-3222. doi:10.1016/j.bmc.2005.12.035
4. Fattorusso C, Campiani G, Kukreja G, Persico M, Butini S, Romano MP, Altarelli M, Ros S, Brindisi M, Savini L, Novellino E, Nacci V, Fattorusso E, Parapini S, Basilico N, Taramelli D, Yardley V, Croft S, Borriello M, Gemma S (2008) Design, synthesis, and structure-Activity relationship studies of 4-quinolinyl-And 9-Acrydinylhydrazones as potent antimalarial agents. J Med Chem 51:1333-1343. doi:10.1021/jm7012375
5. Ferreira ML, Gonçalves RSB, Cardoso LNF, Kaiser CR, Candéa ALP, Henriques MGO, Lourenço MCS, Bezerra FAFM, Souza MVN (2010) Synthesis and antitubercular activity of heteroaromatic isonicotinoyl and 7-chloro-4-quinolinyl hydrazone derivatives. TheScientificWorldJOURNAL 10:1347-1355. doi:10.1100/tsw. 2010.124
6. Foley M, Tilley L (1998) Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol Ther 79:55-87. doi:10.1016/S0163-7258(98)00012-6
7. Font M, Monge A, Ruiz I, Heras B (1997) Structure-Activity relationships in quinoline Reissert derivatives with HIV-1 reverse transcriptase inhibitory activity. Drug Des Discov 14:259-272
8. Kaminsky D, Meltzer RI (1968) Quinolone antibacterial agents: Oxolinic acid and related compounds. J Med Chem 11:160-163. doi:10.1021/jm00307a041
9. Kim EL, Wustenberg R, Rubsam A, Schmitz-Salue C, Warnecke G, Bucker EM, Pettkus N, Speidel D, Rohde V, Schulz-Schaeffer W, Deppert W, Giese A (2010) Chloroquine activates the p53 pathway and induces apoptosis in human glioma cells. Neuro Oncol 12:389-400
10. Krause W, Jordan A, Scholz R, Jimenez JLM (2005) Iodinated nitroimidazoles as radiosensitizers. Anticancer Res 25:2145-2151
11. Montenegro RC, Lotufo LV, Moraes MO, Pessoa CO, Rodrigues FAR, Bispo MLF, Cardoso LNF, Kaiser CR, Souza MVN (2011) Synthesis and antitumoral evaluation of 7-chloro-4-quinolinylhydrazones derivatives. Med Chem 7:599-604
12. Musiol R, Jampilek J, Buchta V, Silva L,Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J (2006) Antifungal properties of newseries of quinoline derivatives. BioorgMedChem 14:3592-3598. doi:10.1016/j.bmc.2006.01.016
13. Savarino A, Di Trani L, Donatelli I, Cauda R, Cassone A (2006) New insights into the antiviral effects of chloroquine. Lancet Infect Dis 6:67-69
14. Sharma P, Sharma JD (2001) In vitro hemolysis of human erythrocytes -by plant extracts with antiplasmodial activity. J Ethnopharmacol 74:239-243
15. Sloboda AE, Powell D, Poletto JF, Pickett WC, Gibbons JJJr, Bell DH, Oronsky AL, Kerwar SS (1991) Antiinflammatory and antiarthritic properties of a substituted quinoline carboxylic acid: CL 306, 293. J Rheumatol 18:855-860
16. Warshakoon NC, Sheville J, Bhatt RT, Ji W, Mendez-Andino JL, Meyers KM, Kim N, Wos JA, Mitchell C, Paris JL, Pinney BB, Reizes O, Hu XE (2006) Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents. Bioorg Med Chem Lett 16:5207-5211