Synthesis of 4-aminoquinoline analogues and their platinum(II) complexes as new antileishmanial and antitubercular agents

Biomedicine and Pharmacotherapy

Volumn 65, Issue 3, 2011, Pages 204-209

  Carmo, Arturene M L ^a   Silva, Flávia M C ^a   Machado, Patrícia A ^a   Fontes, Ana P S ^a   Pavan, Fernando R ^b   Leite, Clarice Q F ^b   Leite, Sergio R de A ^b   Coimbra, Elaine S ^a   Da Silva, Adilson D ^a  

^a FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

4 aminoquinoline analogues; Antileishmanial; Antitubercular; Leishmania; Mycobacterium tuberculosis; Platinum(II) complexes

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; 7 CHLORO N [2 (PROP 2 YNYLAMINO)ETHYL]QUINOLIN 4 AMINE; 7 CHLORO N [3 (PROP 2 YNYLAMINO)PROPYL]QUINOLIN 4 AMINE; 7 CHLORO N [4 (PROP 2 YNYLAMINO)BUTYL]QUINOLIN 4 AMINE; 7 CHLORO N [4 [DI(PROP 2 YNYL)AMINO]BUTYL]QUINOLIN 4 AMINE; 7 CHLORO N [6 (PROP 2 YNYLAMINO)HEXYL]QUINOLIN 4 AMINE; AMPHOTERICIN B; ANTILEISHMANIAL AGENT; ISONIAZID; N (7 CHLOROQUINOLIN 4 YL)BUTHANE 1,4 DIAMINE; N (7 CHLOROQUINOLIN 4 YL)ETHANE 1,2 DIAMINE; N (7 CHLOROQUINOLIN 4 YL)HEXANE 1,6 DIAMINE; N (7 CHLOROQUINOLIN 4 YL)PROPANE 1,3 DIAMINE 2; N [2 [DI(PROP 2 YNYL)AMINO]ETHYL] 7 CHLOROQUINOLIN 4 AMINE; N [3 [DI(PROP 2 YNYL)AMINO]PROPYL]7 CHLOROQUINOLIN 4 AMINE; PLATINUM COMPLEX; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL;

AMINOQUINOLINES; AMPHOTERICIN B; ANTITUBERCULAR AGENTS; COORDINATION COMPLEXES; DIAMINES; LEISHMANIA; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PARGYLINE; PLATINUM;

EID: 79959671242     PISSN: 07533322     EISSN: 19506007     Source Type: Journal    
DOI: 10.1016/j.biopha.2011.01.003     Document Type: Article

References (35)

1. Bentrup K.H., Russell D.G. Mycobacterial persistence: adaptation to a changing environment. Trends Microbiol 2001, 9:597-605.
2. Santos J.L., Yamasaki P.R., Chin C.M., Takashi C.H., Pavan F.R., Leite C.Q. Synthesis and in vitro anti Mycobacterium tuberculosis activity of a series of phthalimide derivatives. Bioorg Med Chem 2009, 1:3795-3799.
3. World Health Organization (WHO). Global tuberculosis control: epidemiology, strategy, financing: WHO report 2009. Available from URL: http://www.who.int/tb/publications/global_report/en/.
4. Ferguson L.A., Rhoads J. Multidrug-resistant and extensively drug-resistant tuberculosis: The new face of an old disease. J Am Acad Nurse Pract 2009, 21:603-609.
5. World Health Organization (WHO). The global MDR-TB & XDR-TB response plan 2007-2008. WHO/HTM/TB/2007.387.
6. Hotez P.J., Molyneux D.H., Fenwick A., Kumaresan J., Sachs S.E., Sachs J.D., et al. Control of neglected tropical diseases. N Engl J Med 2007, 357:1018-1027.
7. Madhuri R., Gill S.S., Kalkar S.R., Wu W., Anderson P.J., Rochon P.A. Oral drug therapy for multiple neglected tropical diseases: a systematic review. JAMA 2007, 29:1911-1924.
8. Santos D.O., Coutinho C.E., Madeira M.F., Bottino C.G., Vieira R.T., Nascimento S.B., et al. Leishmaniasis treatment-a challenge that remains: a review. Parasitol Res 2008, 4:21-32.
9. Cruz A.K., De Toledo J.S., Falade M., Terrão M.C., Kamchonwongpaisan S., Kyle S., et al. Current treatment and drug discovery against Leishmania spp. and Plasmodium spp.: a review. Curr Drug Targets 2009, 10:178-192.
10. Singh R.K., Pandey H.P., Sundar S. Visceral leishmaniasis (kala-azar): challenges ahead. Indian J Med Res 2006, 123:331-344.
11. Vieira N.C., Herrenknecht C., Vacus J., Fournet A., Bories C., Figadère B., et al. Selection of the most promising 2-substituted quinoline as antileishmanial candidate for clinical trials. Biomed Pharmacother 2008, 62:684-689.
12. Strekowski L., Mokrosz J.L., Honkan V.A., Czarny A., Cegla M.T., Wydra R.L., et al. Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4-amines, a new class of anti-HIV-1 agents. J Med Chem 1991, 34:1739-1746.
13. Abel M.D., Luu H.T., Micetich R.G., Nguyen D.Q., Nukatsuka M., Oreski A.B., et al. Cytotoxic quinolines (Part 1) Azolylalkoxyquinolines and azolylalkyl-4(1H)-quinolines. Drug Des Disc 1996, 14:15-30.
14. Abel M.D., Ha C.M., Luu H.T., Micetich R.G., Nguyen D.Q., Oreski A.B., et al. Cytotoxic quinolines (Part 2) Azolylalkylamino and thioquinolines. Drug Des Disc 1996, 14:31-42.
15. Rasoul-Amini S., Khalaj A., Shaffie A., Daneshtalab M., Madadkar-Sobhani A., Fouladdel S., et al. Antitumor activity of new quinoline derivatives in human breast cancer T47D cells. Int J Canc Res 2006, 2:102-108.
16. De D., Krogstad F.M., Byers L.D., Krogstad D.J. Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines. J Med Chem 1998, 41:4918-4926.
17. Vieira L.M., Almeida M.V., Lourenço M.C., Bezerra F.A., Fontes A.P.S. Synthesis and antitubercular activity of palladium and platinum complexes with fluoroquinolones. Eur J Med Chem 2009, 44:4107-4111.
18. Kinnamon K., Steck E.A., Rane D.S. Activity of antitumor drugs against African trypanosomes. Antimicrob Agents Chemother 1979, 15:157-160.
19. Visbal G., Marchan E., Maldonado A., Simoni Z., Navarro M. Synthesis and characterization of platinum-sterol hydrazone complexes with biological activity against Leishmania (L.) mexicana. J Inorg Bioch 2008, 102:547-554.
20. Pavan F.R., Vonpoelhsitz G., Do Nascimento F., Leite S.R.A., Batista A.A., Deflon V.M., et al. Rhutenium (II) phosphine/picolinate complexes as antimycobacterial agents. Eur J Med Chem 2009, 45:598-601.
21. Maia P.I.S., Pavan F.R., Leite C.Q.F., Lemos S.S., Souza G.F., Batista A.A., et al. Vanadium complexes with thiosemicarbazones: Synthesis, characterization, crystal structures and anti-Mycobacterium tuberculosis activity. Polyhedron 2009, 28:398-406.
22. Moro A.C., Mauro A.E., Netto V.G.N., Ananias S.R., Quilles M.B., Zeppone I.C., et al. Antitumor and antimycobacterial activities of cyclopalladated complexes: X-ray structure of [Pd(C2,N-dmba)(Br)(tu)] (dmba=N,N-dimethylbenzylamine, tu=thiourea). Eur J Med Chem 2009, 44:4611-4615.
23. Do Nascimento F., Poelhsitz G.V., Pavan F.R., Sato D.N., Leite C.Q.F., de Araujo H.S., et al. Synthesis, characterization, X-ray structure and in vitro antimycobacterial and antitumoral activities of Ru(II) phosphine/diimine complexes containing the SpymMe2 ligand, SpymMe2=4,6-dimethyl-2-mercaptopyrimidine. J Inorg Biochem 2008, 102:1783-1789.
24. Tarallo M.B., Costa-Filho A.J., Vieira E.D., Monge A., Leite C.Q.F., Pavan F.R., et al. Research of new mixed-chelate copper complexes with Quinoxaline N1,N4-dioxide derivatives and Alanine as ligands, potential antimycobacterial agents. Anales de la Asociación Química Argentina 2009, 97:80-89.
25. M'Bongo N., Loiseau P.M., Lawrence F., Bories C., Craciunescu D.G., Robert-Gero M. Synergistic effect of Ir-(COT)-pentamidine alizarin red and pentamidine, amphotericin B, and paromomycin on Leishmania donovani. Parasitol Res 1997, 83:515-517.
26. Tavares J., Ouaissi M., Ouaissi A., Cordeiro-da-Silva A. Characterization of the anti-Leishmania effect induced by cisplatin, an anticancer drug. Acta Tropica 2007, 103:133-141.
27. Kaur S., Sachdeva H., Dhuria S., Sharma M., Kaur T. Antileishmanial effect of cisplatin against murine visceral leishmaniasis. Parasitol Int 2010, 59:62-69.
28. Musonda C.C., Gut J., Rosenthal P.J., Yardley V., de Souza R.C.C., Chibale K. Application of multicomponent reactions to antimalarial drug discovery. Part 2: New antiplasmodial and antitrypanosomal 4-aminoquinoline gamma- and delta-lactams via a 'catch and release' protocol. Bioorg Med Chem 2006, 14:5605-5615.
29. Croft S., Barrett M.P., Urbina J. Chemotherapy of trypanosomiases and leishmaniasis. Trends Parasitol 2005, 21:508-512.
30. Braga F.G., Coimbra E.S., Matos M.O., Carmo A.M.L., Cancio M.D., Da Silva A.D. Synthesis and biological evaluation of some 6-substituted purines. Eur J Med Chem 2007, 42:530-537.
31. Franzblau S.G., Witzig R.S., McLaughlin J.C., Torres P., Madico G., Hernandez A., et al. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol 1998, 36:362-366.
32. Palomino J.C., Martin A., Camacho M., Guerra H., Swings J., Portaela F. Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrob Agents Chemother 2002, 46:2720-2722.
33. Solaja B.A., Opsenica D., Smith K.S., Milhous W.K., Terzic N., Opsenica I., et al. Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A. J Med Chem 2008, 51:4388-4391.
34. Solomon V.R., Puri S.K., Srivastava K., Katti S.B. Design and synthesis of new antimalarial agents from 4-aminoquinoline. Bioorg Med Chem 2005, 13:2157-2165.
35. Nelson P.H., Unger S.H. Eur Pat Appl 1986, 39.