4-Aminoquinoline-β-lactam conjugates: Synthesis, antimalarial, and antitubercular evaluation

Chemical Biology and Drug Design

Volumn 83, Issue 2, 2014, Pages 191-197

  Raj, Raghu ^a   Biot, Christophe ^b   Carrère Kremer, Séverine ^c   Kremer, Laurent ^c   Guérardel, Yann ^b   Gut, Jiri ^d   Rosenthal, Philip J ^d   Kumar, Vipan ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

^b UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

^c UNIVERSITÉ DE MONTPELLIER   (France)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

4 aminoquinoline lactam conjugates; antimalarial evaluation; antitubercular evaluation; molecular hybridization; structure activity relationship

Indexed keywords

4 AMINOQUINOLINE BETA LACTAM; 4 AMINOQUINOLINE DERIVATIVE; ANTIMALARIAL AGENT; BETA LACTAM; CEFALEXIN; CHLOROQUINE; ETHIONAMIDE; ISONIAZID; RIFAMPICIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIMALARIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; CONJUGATE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; HYBRID; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL;

PLASMODIUM FALCIPARUM;

4-AMINOQUINOLINE-Β-LACTAM CONJUGATES; ANTIMALARIAL EVALUATION; ANTITUBERCULAR EVALUATION; MOLECULAR HYBRIDIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

AMINOQUINOLINES; ANTIMALARIALS; ANTITUBERCULAR AGENTS; BETA-LACTAMS; DRUG EVALUATION, PRECLINICAL; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84892547309     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12225     Document Type: Article

References (36)

1. Chauhan P.M.S., Srivastava S.K., (2001) Present Trends and Future Strategy in Chemotherapy of Malaria. Curr Med Chem; 8: 1535-1542.
2. Jefford C.W., (2001) Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. Curr Med Chem; 8: 1803-1826.
3. Burrows J.N., Chibale K., Wells T.N.C., (2011) The state of the art in anti-malarial drug discovery and development. Curr Top Med Chem; 11: 1226-1254.
4. Dondorp M., Nosten F., Yi P., Das D., Phyo A.P., Tarning J., Lwin K.M., et al,. (2009) Artemisinin resistance in Plasmodium falciparum malaria. N Engl J Med; 361: 455-469.
5. Schlitzer M., (2007) Malaria chemotherapeutics part I: history of antimalarial drug development, Currently used therapeutics, and drugs in clinical development. ChemMedChem; 2: 944-986.
6. Meunier B., (2008) Hybrid molecules with a dual mode of action: dream or reality? Acc Chem Res; 41: 69-77.
7. Muregi F.W., Ishih A., (2010) Next-generation antimalarial drugs: hybrid molecules as a new strategy in drug design. Drug Dev Res; 71: 20-32.
8. Viegas-Junior C., Danuello A., da Silva Bolzani V., Barreiro E.J., Fraga C.A.M., (2007) Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem; 14: 1829-1852.
9. Cabaret O.D., Vical F.B., Robert A., Meunier B., (2000) Preparation and antimalarial activities of "trioxaquines", new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline. ChemBioChem; 1: 281-283.
10. Diacon A.H., Pym A., Grobush M., Patienta R., Rustomjee R., Page-Shipp L., Pistorius C., et al,. (2009) The diarylquinoline TMC207 for multidrug-resistant tuberculosis. N Eng J Med; 360: 2397-2405.
11. Veziris N., Ibrahim M., Lounis N., Andries T., Jarlier V., (2011) Sterilizing activity of second-line regimens containing TMC207 in a murine model of tuberculosis. PLoS ONE; 6: 17556.
12. Guillenmont J., Meyer C., Poncelet A., Bourdrez X., Andries K., (2011) Diarylquinolines, synthesis pathways and quantitative structure-activity relationship studies leading to the discovery of TMC207. Future Med Chem; 3: 1345-1360.
13. Nava-Zuazo C., Estrada-Soto S., Guerrero-Álvarez J., Rivera I.L., Molina-Salinas G.M., Said-Fernández S., Chan-Bacab M.J., Cedillo-Rivera R., Moo-Puc R., Miron-Lõpez G., Navarrete-Vazquez G., (2010) Design, synthesis, and in vitro antiprotozoal, antimycobacterial activities of N-{2-[(7-chloroquinolin-4-yl)amino]ethyl}ureas. Bioorg Med Chem; 18: 6398-6403.
14. Candéa A.L.P., Ferreira M.L., Pais K.C., Cardoso L.N.F., Kaiser C.R., Henriques M.G.M.O., Lourenço M.C.S., Bezerra F.A.F.M., De Souza M.V.N., (2009) Synthesis and antitubercular activity of 7-chloro-4- quinolinylhydrazones derivatives. Bioorg Med Chem Lett; 19: 6272-6274.
15. Konaklieva M.I., (2002) β-lactams as inhibitors of serine enzymes. Curr Med Chem Anti-Infect Agents; 1: 215-238.
16. Cainelli G., Galletti P., Garbisa S., Giacomini D., Sartor L., Quintavalla A., (2003) 4-alkylidene-azetidin-2-ones: novel inhibitors of leukocyte elastase and gelatinase. Bioorg Med Chem; 11: 5391-5399.
17. Kazi A., Hill R., Long T.E., Kuhn D.J., Turos E., Dou Q.P., (2004) Novel N-thiolated beta-lactam antibiotics selectively induce apoptosis in human tumor and transformed, but not normal or nontransformed, cells. Biochem Pharmacol; 67: 365-374.
18. Wright A.J., (1999) The penicillins. Mayo Clin Proc; 74: 290-307.
19. Wilke M.S., Lovering A.L., Strynadka N.C.J., (2005) Beta-lactam antibiotic resistance: a current structural perspective. Curr opn Microbio; 8: 525-533.
20. Kasik J.E., (1965) The nature of mycobacterial penicillinase. Am Rev Respir Dis; 91: 117-119.
21. Kasik J., (1979) Mycobacterial beta-lactamases. In:, Hamilton-Miller J., Smith J., editor. Beta-lactamases. London: Academic Press; p. 339.
22. Hugonnet J.E., Tremblay L.W., Boshoff H.I., Barry C.E. III, Blanchard J.S., (2009) Meropenem-clavulanate is effective against extensively drug-resistant Mycobacterium tuberculosis. Science; 323: 1215-1218.
23. Kumar P., Arora K., Lloyd J.R., Lee I.Y., Nair V., Fischer E., Boshoff H.I.M., Barry C.E. III, (2012) Meropenem inhibits D,D-carboxypeptidase activity in Mycobacterium tuberculosis. Mol Microbio; 86: 367-381.
24. Singh P., Raj R., Kumar V., Mahajan M.P., Bedi P.M.S., Kaur T., Saxena A.K., (2011) 1,2,3-Triazole tethered β-lactam-chalcone bifunctional hybrids: synthesis and anticancer evaluation. Eur J Med Chem; 47: 594-600.
25. Raj R., Singh P., Haberkern N.T., Faucher R.M., Land K.M., Kumar V., (2013) synthesis of 1H-1,2,3-triazole linked β-lactam-isatin bi-functional hybrids and preliminary analysis of in vitro activity against the protozoal parasite Trichomonas vaginalis. Eur J Med Chem; 63: 897-906.
26. Raj R., Singh P., Singh P., Gut J., Rosenthal P.J., Kumar V., (2013) Azide-alkyne cycloaddition en route towards 1H-1,2,3-triazole-tethered β-lactam-ferrocene and β-lactam-ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation. Eur J Med Chem; 62: 590-596.
27. Kumar K., Carrère-Kremer S., Kremer L., Guérardel Y., Biot C., Kumar V., (2013) Azide-alkyne cycloaddition en route towards 1H-1,2,3-triazole-tethered β-lactam-ferrocene and β-lactam- ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation. Dalton Trans; 42: 1492-1500.
28. Kumar K., Carrère-Kremer S., Kremer L., Guérardel Y., Biot C., Kumar V., (2013) 1H-1,2,3-Triazole-Tethered Isatin-Ferrocene and Isatin-Ferrocenylchalcone Conjugates: synthesis and in vitro Anti-tubercular Evaluation. Organometallics. doi: 10.1021/om301157z.
29. Jensen J.B., (2002) In vitro culture of plasmodium parasites. In:, Doolan D.L., editor. Malaria Methods and Protocols. Totowa, NJ: Humana; p. 477-488.
30. Singh A., Rosenthal P.J., (2001) Comparison of efficacies of cysteine protease inhibitors against five strains of Plasmodium falciparum. Antimicrob Agents Chemother; 45: 949-951.
31. Sambandamurthy V.K., Derrick S.C., Hsu T., Chen B., Larsen M.H., Jalapathy K.V., Chen M., Kim J., Porcelli S.A., Chan J., Morris S.L., Jacobs W.R., (2006) Mycobacterium tuberculosis DeltaRD1 DeltapanCD: a safe and limited replicating mutant strain that protects immune competent and immune compromised mice against experimental tuberculosis. Vaccine; 24: 6309-6320.
32. Kremer L., Douglas J.D., Baulard A.R., Morehouse C., Guy M.R., Alland D., Dover L.G., Lakey J.H., Jacobs W.R. Jr, Brennan P.J., Minnikin D.E., Besra G.S., (2000) Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis. J Biol Chem; 275: 16857-16864.
33. Mehra V., Singh P., Kumar V., (2012) β-Lactam-synthon-interceded diastereoselective synthesis of functionally enriched thioxo-imidazolidines, imidazolidin-2-ones, piperazine-5,6-diones and 4,5-dihydroimidazoles. Tetrahedron; 68: 8395-8402.
34. Sulejman A., Kristina S., (2010) 3′-N-Substituted 9-deoxo-9A-methyl-9A-aza-homoerythromycin having antimalarial activity, WIPO Patent Application WO/2010/086351A1.
35. Singh P., Sachdeva S., Raj R., Kumar V., Mahajan M.P., Nasser S., Vivas L., Gut J., Rosenthal P.J., Feng T.S., Chibale K., (2011) Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives. Bioorg Med Chem Lett; 21: 4561-4563.
36. Slayden R.A., Belisle J.T., (2009) Morphological features and signature gene response elicited by inactivation of FtsI in Mycobacterium tuberculosis. J Antimicrob Chemother; 63: 451-457.