7-chloroquinoline-isatin conjugates: Antimalarial, antitubercular, and cytotoxic evaluation

Chemical Biology and Drug Design

Volumn 83, Issue 5, 2014, Pages 622-629

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

^a GURU NANAK DEV UNIVERSITY   (India)

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

^c UNIVERSITÉ DE MONTPELLIER   (France)

^d INSERM   (France)

^e UNIVERSITY OF CALIFORNIA   (United States)

^f UNIVERSITY OF MONS   (Belgium)

Author keywords

7 chloroquinoline isatin scaffolds; antimalarial activity; antitubercular activity; cytotoxicity; structure activity relationship

Indexed keywords

7 CHLORO 4 PIPERAZIN 1 YL QUINOLINE; 7 CHLOROQUINOLINE ISATIN; ARTEMISININ; BEDAQUILINE; CEFALEXIN; CHLOROQUINE; ISATIN DERIVATIVE; ISONIAZID; PIPERAQUINE; UNCLASSIFIED DRUG; ANTIMALARIAL AGENT; ISATIN; TUBERCULOSTATIC AGENT;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL STRAIN; CELL LINE; CONJUGATE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG SENSITIVITY; DRUG SYNTHESIS; EMBRYO; FIBROBLAST CULTURE; HUMAN; IC 50; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; ANIMAL; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; DRUG RESISTANCE; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TOXICITY;

MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; ANTITUBERCULAR AGENTS; CELL LINE; CELL SURVIVAL; CHLOROQUINE; DRUG RESISTANCE; ISATIN; MICE; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899473320     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12273     Document Type: Article

References (50)

1. Pasqualoto K.F.M., Ferreira E.I., Santos-Filho O.A., Hopfinger A.J., (2004) Rational design of new antituberculosis agents: receptor-independent four-dimensional quantitative structure-activity relationship analysis of a set of isoniazid derivatives. J Med Chem; 47: 3755-3764. (Pubitemid 38900342)
2. Jones D., (2005) Antibacterial drugs: tackling tuberculosis. Nat Rev Drug Disc; 4: 103.
3. Gandhi N.R., Moll A., Sturm A.W., Pawinski R., Govender T., Lalloo U., Zeller K., Andrews J., Friedland G., (2006) Extensively drug-resistant tuberculosis as a cause of death in patients co-infected with tuberculosis and HIV in a rural area of South Africa. Lancet; 368: 1575-1580. (Pubitemid 44780738)
4. Veziris N., Truffot-Pernot C., Aubry A., Jarlier V., Lounis N., (2003) Fluoroquinolone-containing third-line regimen against Mycobacterium tuberculosis in vivo. Antimicrob Agents Chemother; 47: 3117-3122. (Pubitemid 37229566)
5. Caminero J.A., Sotgiu G., Zumla A., Migliori G.B., (2010) Best drug treatment for multidrug-resistant and extensively drug-resistant tuberculosis. Lancet Infect Dis; 10: 621-629.
6. Ridley R.G., (2002) Medical need, scientific opportunity and the drive for antimalarial drugs. Nature; 415: 686-693. (Pubitemid 34136402)
7. Egan T.J., Ncokazi K.K., (2005) Quinoline antimalarials decrease the rate of beta-hematin formation. J Inorg Biochem; 99: 1532-1539. (Pubitemid 40804963)
8. Joshi A.A., Viswanathan C.L., (2006) Recent developments in antimalarial drug discovery. Anti Infect Agents Med Chem; 5: 105-122. (Pubitemid 43796668)
9. Hyde J.E., (2007) Drug-resistant malaria- An insight. FEBS J; 274: 4688-4698.
10. Hwang J.Y., Kawasuji T., Lowes D.J., Clark J.A., Connelly M.C., Zhu F., Guiguemde W.A., Sigal M.S., Wilson E.B., DeRisi J.L., Guy R.K., (2011) Synthesis and evaluation of 7-substituted 4-aminoquinoline analogues for antimalarial activity. J Med Chem; 54: 7084-7093.
11. Manohar S., Rajesh U.C., Khan S.I., Tekwani B.L., Rawat D.S., (2012) Novel 4-aminoquinoline-pyrimidine based hybrids with improved in Vitro and in vivo antimalarial activity. ACS Med Chem Lett; 3: 555-559.
12. Ekoue-Kovi K.A., Yearick K., Iwaniuk D.P., Natarajan J.K., Alumasa J., de Dios A.C., Roepe P.D., Wolf C., (2009) Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas. Bioorg Med Chem; 17: 270-283.
13. Natarajan J.K., Alumasa J.N., Yearick K., Ekoue-Kovi K.A., Casabianca L.B., de Rios A.C., Wolf C., Roepe P.D., (2008) 4-N-, 4-S-, and 4-O-chloroquine analogues: influence of side chain length and quinolyl nitrogen pKa on activity vs chloroquine resistant malaria. J Med Chem; 51: 3466-3479. (Pubitemid 351875003)
14. Biot C., Nosten F., Fraisse L., Ter-Minassian D., Khalife J., Drive D., (2011) The antimalarial ferroquine: from bench to clinic. Parasite; 18: 207-214.
15. Guantai E.M., Ncokazi K., Egan T.J., Gut J., Rosenthal P.J., Smith P.J., Chibale K., (2010) Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds. Bioorg Med Chem; 18: 8243-8256.
16. Singh P., Raj R., Singh P., Gut J., Rosenthal P.J., Kumar V., (2014) Urea/oxalamide tethered β-lactam-7-chloroquinoline conjugates: synthesis and in vitro antimalarial evaluation. Eur J Med Chem; 71: 128-134.
17. 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.
18. Ratan B.T., Anand B., Yogeeswari P., Sriram D.H., (2005) Synthesis and evaluation of anti-HIV activity of isatin beta-thiosemicarbazone derivatives. Bioorg Med Chem Lett; 15: 4451-4455. (Pubitemid 41253873)
19. Jiang T., Kuhen K.L., Wolff K., Yin H., Bieza K., Caldwell J., Bursulaya B., Tuntland T., Zhang K., Karanewsky D., He Y., (2006) Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2. Bioorg Med Chem Lett; 16: 2109-2112. (Pubitemid 43351060)
20. Tripathy R., Reiboldt A., Messina P.A., Iqbal M., Singh J., Bacon E.R., Angeles Th.S., Yang Sh.X., Albom M.S., Robinson C., Chang H., Ruggeri B.A., Mallamo J.P., (2006) Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis. Bioorg Med Chem Lett; 16: 2158-2162. (Pubitemid 43351070)
21. Cane A., Tournaire M.C., Barritault D., Crumeyrolle-Arias M., (2000) The endogenous oxindoles 5-hydroxyoxindole and isatin are antiproliferative and proapoptotic. Biochem Biophys Res Commun; 276: 379-384.
22. Silveira V.Ch., Luz J.S., Oliveira C.C., Graziani I., Ciriolo M.R., Costa-Ferreira A.M., (2008) Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity. J Inorg Biochem; 102: 1090-1103.
23. Amal R.A., Raghunathan R., Sridevikumaria M.R., Raman N., (2003) Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines. Bioorg Med Chem; 11: 407-419. (Pubitemid 36051031)
24. Rodriguez-Arguelles M.C., Mosquera-Vazaquez S., Touron-Touceda P., Sanmartin- Matalobos J., Garcia-Deibe A.M., Belicchi-Ferraris M., Pelosi G., Pelizzi C., Zani F., (2007) Complexes of 2-thiophenecarbonyl and isonicotinoyl hydrazones of 3-(N-methyl)isatin. A study of their antimicrobial activity. J Inorg Biochem; 101: 138-147. (Pubitemid 44879612)
25. Maskell L., Blanche E.A., Colucci M.A., Whatmore J.L., Moody Ch.J., (2007) Synthesis and evaluation of prodrugs for anti-angiogenic pyrrolylmethylidenyl oxindoles. Bioorg Med Chem Lett; 17: 1575-1578. (Pubitemid 46274355)
26. Verma M., Nath P.S., Nand S.K., Stables J.P., (2004) Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm; 54: 49-56. (Pubitemid 38524314)
27. Igosheva N., Lorz C., O'Conner E., Glover V., Mehmet H., (2005) Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem Int; 47: 216-224. (Pubitemid 40848684)
28. Yeung B.K.S., Zou B., Rottmann M., Lakshminarayana S.B., Ang S.H., Leong S.Y., Tan J., et al,. (2010) Spirotetrahydro beta-carbolines (spiroindolones): a new class of potent and orally efficacious compounds for the treatment of malaria. J Med Chem; 53: 5155-5164.
29. Rottmann M., McNamara C., Yeung B.K.S., Lee M.C.S., Zhou B., Russell B., Seitz P., et al,. (2010) Spiroindolones, a potent compound class for the treatment of malaria. Science; 329: 1175-1180.
30. Hans R.H., Wiid I.J.F., Helden P.D.V., Wan B., Franzblau S.G., Gut J., Rosenthal P.J., Chibale K., (2011) Novel thiolactone-isatin hybrids as potential antimalarial and antitubercular agents. Bioorg Med Chem Lett; 21: 2055-2058.
31. Raj R., Singh P., Singh P., Gut J., Rosenthal P.J., Kumar V., (2013) Azide-alkyne cycloaddition en route to 1H-1,2,3-triazole-tethered 7-chloroquinoline-isatin chimeras: synthesis and antimalarial evaluation. Eur J Med Chem; 62: 590-596.
32. Raj R., Biot C., Carrère-Kremer S., Kremer L., Guérardel Y., Gut J., Rosenthal P.J., Kumar V., (2013) 4-aminoquinoline-β-lactam conjugates: synthesis, antimalarial and anti-tubercular evaluation. Chem Biol Drug Des (Accepted manuscript): doi: 10.1111/cbdd.12225
33. Raj R., Singh P., Haberkern N.T., Faucher R.M., Patel N., 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.
34. Nisha, Mehra V., Hopper M., Patel N., Hall D., Wrischnik L.A., Land K.M., Kumar V., (2013) Design and synthesis of β-amino alcohol based β-lactam-isatin chimeras and preliminary analysis of in vitro activity against the protozoal pathogen Trichomonas vaginalis. MedChemComm; 4: 1018-1024.
35. 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; 32: 5713-5719.
36. Biamonte M.A., Wanner J., Le Roch K.G., (2013) Recent advances in malaria drug discovery. Bioorg Med Chem Lett; 23: 2829-2843.
37. Kumar V., Mahajan A., Chibale K., (2009) Synthetic medicinal chemistry of selected antimalarial natural products. Bioorg Med Chem; 17: 2236-2275.
38. Forge D., Cappoen D., Laurent J., Stanicki D., Mayence A., Huang T.L., Verschaeve L., Huygen K., Eynde J.J.V., (2012) 1,4-diarylpiperazines and analogs as anti-tubercular agents: synthesis and biological evaluation. Eur J Med Chem; 49: 95-101.
39. Eynde J.J.V., Mayence A., Lecour L. Jr, Huang T.L., (2003) Synthesis, antituberculosis activity, and DNA binding affinity of a highly diverse library of 1,4-diarylpiperazines. Med Chem Res; 12: 401-414. (Pubitemid 38822565)
40. Figueiredo R., Ramos D.F., Moiteiro C., Medeiros M.A., Curto M.J.M., de Menezes J.C., Pando R.H., Silva P.E.A., Costa M.D.C., (2012) Pharmacophore insights into rpoB gene mutations in Mycobacterium tuberculosis rifampicin resistant isolates. Eur J Med Chem; 47: 186-193.
41. Krishnan S.S., Pandeya N.S., Stables J.P., Ramesh A., (2002) Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur J Pharm Sci; 16: 129-132. (Pubitemid 34786446)
42. Sridhar S.K., Ramesh A., (2001) Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biol Pharm Bull; 24: 1149-1152. (Pubitemid 33049077)
43. Sriram D., Yogeeswari P., Gopal G., (2005) Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs. Eur J Med Chem; 40: 1373-1376. (Pubitemid 41618280)
44. Karali N., Gursoy A., Kandemirli F., Shvets N., Kaynak F.B., Ozbey S., Kovalishyn V., Dimoglo A., (2007) Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg Med Chem; 15: 5888-5904. (Pubitemid 47043467)
45. Karali N., (2002) Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives. Eur J Med Chem; 37: 909-918. (Pubitemid 35356427)
46. Terzioglu N., Karali N., Gursoy A., Pannecouque C., Leysen P., Paeshuyse J., Neyts J., De Clercq E., (2006) Synthesis and primary antiviral activity evaluation of 3-hydrazono-5-nitro-2-indolinone derivatives. ARKIVOC; 1: 109-118. (Pubitemid 41586738)
47. 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.
48. 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. (Pubitemid 32182053)
49. 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. (Pubitemid 30398921)
50. Kumar V., Chipeleme A., Chibale K., (2008) Effect of varying the anionic component of a copper (I) catalyst on homologation of arylacetylenes to allenes by the Mannich reaction. Eur J Org Chem; 43-46.