Synthesis of [(7-chloroquinolin-4-yl)amino]chalcones: Potential antimalarial and anticancer agents

Scientia Pharmaceutica

Volumn 77, Issue 4, 2009, Pages 725-741

  Ferrer, Rosa ^a   Lobo, Gricela ^a   Gamboa, Neira ^a   Rodrigues, Juan ^a,b   Abramjuk, Claudia ^b   Jung, Klaus ^b   Lein, Michael ^b,c   Charris, Jaime E ^a  

^a UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

^b CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

^c Berlin Institute for Urologic Research   (Germany)

Author keywords

Hematin; Cancer; CQ; Malaria; Prostate

Indexed keywords

1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (2 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (2 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (3 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (3 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (4 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 [4 (DIMETHYLAMINO)PHENYL]PROP 2 EN 1 ONE; 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 PHENYLPROP 2 EN 1 ONE; 1 [4 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (4 FLUOROPHENYL)PROP 2 EN 1 ONE; 1 [4 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [4 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL] 3 [4 (DIMETHYLAMINO)PHENYL]PROP 2 EN 1 ONE; 3 (2 CHLOROPHENYL) 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL]PROP 2 EN 1 ONE; 3 (3 CHLOROPHENYL) 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL]PROP 2 EN 1 ONE; 3 (4 CHLOROPHENYL) 1 [4 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL]PROP 2 EN 1 ONE; 3 [4 CHLOROPHENYL) 1 [3 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL]PROP 2 EN 1 ONE; [(7 CHLOROQUINOLIN 4 YL)AMINO]CHALCONE DERIVATIVE; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; CHLOROQUINE; GLOBIN; HEMATIN; HEME; LEUPEPTIN; PEPSTATIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN LNCAP; CONTROLLED STUDY; CRYSTALLIZATION; CYTOTOXICITY; DOSE RESPONSE; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MALE; MOUSE; NONHUMAN; PROSTATE TUMOR; PROTEIN DEGRADATION; TUMOR CELL;

EID: 74549115186     PISSN: 00368709     EISSN: 22180532     Source Type: Journal    
DOI: 10.3797/scipharm.0905-07     Document Type: Article

References (29)

1. WHO World Malaria Report. 2008 (http://rbm.who.int/wmr2008).
2. Coatney G, Cooper W, Eddy N, Grennberg J. Survey of antimalarial agents. Public Health Monogr. 1953; 15: 1-322.
3. Greenwood D. Conflicts of interest: The genesis of synthetic antimalarial agents in peace and war. J Antimicrob Chemother. 1995; 36: 857-872. doi:10.1093/jac/36.5.857
4. Fitch C. Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004; 74: 1957-1972. doi:10.1016/j.lfs. 2003.10.003
5. White N. Drug resistance in malaria. Br Med Bull. 1998; 54: 703-715. PMid:10326295
6. Watkins W, Sixsmith D, Spencer H, Boriga D, Karjuki D, Kipingor T, Koech D. Effectiveness of amodiaquine as a treatment for chloroquine resistant Plasmodium falciparum. Lancet. 1984; 1: 357-359. doi:10.1016/S0140- 6736(84)90410-0
7. Ruscoe J, Tingle M, O'Neill P, Magg J, Ward S, Park B. Effect of disposition of Manich antimalarial agents on the pharmacology and toxicology. Antimicrob Agents Chemother. 1998; 42: 2410-2416. PMid:9736572
8. O'Neill P, Mukhtar A, Stocks P, Randle L, Hindley S, Ward S, Storr R, Bickley J, O'Neill I, Maggs J, Hughes R, Winstanley P, Bray P, Park B. Isoquine and related amodiaquine analogs: A new generation of improved 4-aminoquinoline antimalarials. J Med Chem. 2003; 46: 4933-4945. doi:10.1021/jm030796n
9. w-oxides. J Med Chem. 1986; 29: 924-939. doi:10.1021/jm00156a009
10. Neill P, Willock D, Hawley S, Bray P, Storr R, Ward S, Park B. Synthesis, antimalarial activity, and molecular modelling of tebuquine analogues. J Med Chem. 1997; 40: 437-448. doi:10.1021/jm960370r
11. Biot C, Chibale K. Novel approaches to antimalarial drug discovery. Infect Disord Drug Targets. 2006; 6: 173-204. doi:10.2174/187152606784112155
12. Goldberg D, Slater A, Cerami A, Henderson G. Hemoglobin degradation in the malaria parasite Plasmodium falciparum: an ordered process in a unique organelle. Proc Natl Acad Sci U S A. 1990; 87: 2931-2935. doi:10.1073/pnas.87.8.2931
13. Martirosyan A, Rahim-Bata R, Freeman A, Clarke C, Howard R, Strobl J. Differentiation-inducing quinolines as experimental breast cancer agents in the MCF-7 human cancer cell model. Biochem Pharmacol. 2004; 68: 1729-1738. doi:10.1016/j.bcp.2004.05.003
14. Mól W, Matyja M, Filip B, Wietrzyk S. Synthesis and antiproliferative activity in vitro of novel (2-buthynyl)thioquinolines. Bioorg Med Chem. 2008; 16: 8136-8141. doi:10.1016/j.bmc.2008.07.047
15. Lukevics E, Abele E, Arsenyan P, Abele R, Rubina K, Shestakova I, Domracheva I, Vologdina V. Synthesis and citotoxicity of Silicon containing pyridine and quinoline sulfides. Met Based Drugs. 2002; 9: 45-51. doi:10.1155/MBD.2002.45
16. Shahabuddin M, Nambiar M, Choudhary B, Advirao G, Raghavan S. A novel DNA intercalator, butylamino-pyrimido[4′,5′:4,5]selenolo(2,3-b) quinoline, induces cell cycle arrest and apoptosis in leukemic cell. Invest New Drugs. 2009; in press. doi:10.1007/s10637-008-9212-6
17. Jasinki P, Welsh B, Galvez J, Land D, Zwolak P, Ghandi L, Terai K, Dudek A. A novel quinoline, MT477: suppresses cell signaling through Ras molecular patway, inhibits PKC activity, and demonstrates in vivo anti-tumor activity against human carcinoma cell lines. Invest New Drugs. 2008; 26: 223-232. doi:10.1007/s10637-007-9096-x
18. Smith E, Schwartz M, Kawamoto H, You X, Hwang D, Liu H, Scherr D. Antitumor effects of imidazoquinolines in urothelial cell carcinoma of the bladder. J Urol. 2007; 177: 2347-2351. doi:10.1016/j.juro.2007.01.112
19. Isaacs J, Pili R, Qian D, Dalrymple S, Garrison J, Kyprianou N, Björk A, Olsson A, Leanderson T. Identification of ABR-215050 as lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer. Prostate. 2006; 66: 1768-1778. doi:10.1002/pros.20509
20. Charris J, Domínguez J, Gamboa N, Rodrigues J, Angel J. Synthesis and antimalarial activity of E-2-quinolinylbenzocycloalcanones. Eur J Med Chem. 2005; 40: 875-881. doi:10.1016/j.ejmech.2005.03.013
21. Baelmans R, Deharo E, Muñoz V, Sauvain M, Ginsburg H. Experimental conditions for testing the inhibitory activity of chloroquine on the formation of β-hematin. J Exp Parasitol. 2000; 4: 243-248. doi:10.1006/expr.2000.4558
22. Jemal A, Thomas A, Murray T, Thun M. Cancer statistics, 2002. CA Cancer J. Clin. 2002; 52: 23-47. doi:10.3322/canjclin.52.1.23
23. Chen D, Cui Q, Yang H, Barrea R, Sarkar F, Sheng S, Yan B, Reddy G, Dou Q. Clioquinol, a therapeutic agent for Alzheimer's disease, has proteasome-inhibitory, androgen receptor-suppressing, apoptosis-inducing, and antitumor activities in human prostate cancer cells and xenografts. Cancer Res. 2007; 67: 1636-1644. doi:10.1158/0008-5472.CAN-06-3546
24. Zhou J, Geng G, Batist G, Wu J. Syntheses and potential anti-prostate cancer activities of ionone-based chalcones. Bioorg Med Chem Lett. 2009; 19: 1183-1186. doi:10.1016/j.bmcl.2008.12.089
25. Denizot F, Lang R. Rapid colorimetric assay for cell grow and survival modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Meth. 1986; 89: 271-277. doi:10.1016/0022-1759(86)90368-6
26. Egan T. Haemozoin formation as a target for the rational design of new antimalarials. Drug Des Rev. 2004; 1: 93-110. doi:10.2174/1567269043480744
27. Chauhan P, Pratap R, Sharma S. Synthesis and antiparasitic activity of 4-(aryl/heteroarylamino)-7-chloroquinolines. Indian J Chem. 1985; 24B: 1154-1157.
28. Deharo E, Gautret P, Ginsburg H, Chabaud A, Landau I. Synchronization of Plasmodium yoelii nigeriensis and P. killicki infection in the mose by means of percoll-glucose gradient stage fractionation: Determination of the duration of the schizogonic cycle. Parasitol Res. 1994; 80: 159-164. doi:10.1007/BF00933785
29. Rosenthal P. Plasmodium falciparum: effects of proteinase inhibitors on globin hydrolysis by cultured malaria parasites. Exp Parasitol. 1995; 80: 272-281. doi:10.1006/expr.1995.1033