Synthesis of 4-aminoquinoline-1,2,3-triazole and 4-aminoquinoline-1,2,3-triazole-1,3,5-triazine hybrids as potential antimalarial agents

Chemical Biology and Drug Design

Volumn 78, Issue 1, 2011, Pages 124-136

  Manohar, Sunny ^a   Khan, Shabana I ^b   Rawat, Diwan S ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Antimalarial; Hybrids; Plasmodium falciparum

Indexed keywords

(7 CHLORO QUINOLIN 4 YL) [2 (4 3 TOLYLOXYMETHYL[1,2,3]TRIAZOL 1 YL)ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 (4 4 TOLYLOXYMETHYL[1,2,3]TRIAZOL 1 YL)ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 (3,4 DIMETHYLPHENOXYMETHYL)[1,2,3]TRIAZOL 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 (4 CYCLOPROPYLAMINO 6 MORPHOLIN 4 YL [1,3,5]TRIAZIN 2 YLOXYMETHYL) [1,2,3]TRIAZOL 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 (4 CYCLOPROPYLAMINO 6 PIPERIDIN 1YL [1,3,5]TRIAZIN 2 YLOXYMETHYL) [1,2,3]TRIAZOL 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 (4 ISOPROPYLPHENOXYMETHYL)[1,2,3]TRIAZOL 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 (4 NITROPHENOXYMETHYL) [1,2,3]TRIAZOL 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 (NAPHTHALEN 2 YLOXYMETHYL) [1,2,3]TRIAZOL- 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [2 [4 [4 (3,5 DIMETHOXYPHENYL AMINO) 6 MORPHOLIN 4 YL [1,3,5]TRIAZIN 2 YLOXYMETHYL] [1,2,3]TRIAZOL 1 YL]ETHYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [3 [4 (4 CYCLOPROPYLAMINO 6 MORPHOLIN 4 YL [1,3,5]TRIAZIN 2 YLOXYMETHYL) [1,2,3]TRIAZOL 1 YL] PROPYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [3 [4 (NAPHTHALEN 2 YLOXYMETHYL) [1,2,3]TRIAZOL 1 YL]PROPYL]AMINE; (7 CHLORO QUINOLIN 4 YL) [3 [4 [4 (3,5 DIMETHOXYPHENYLAMINO) 6 MORPHOLIN 4 YL [1,3,5] TRIAZIN 2 YLOXYMETHYL] [1,2,3]TRIAZOL 1 YL]PROPYL]AMINE; 1 [1 [3 (7 CHLORO QUINOLIN 4 YLAMINO)PROPYL] 1H [1,2,3]TRIAZOL 4 YL]CYCLOHEXANOL; 1 [4 [1 [3 (7 CHLORO QUINOLIN 4 YLAMINO)PROPYL] 1H [1,2,3]TRIAZOL 4 YLMETHOXY]PHENYL]ETHANONE; 4 AMINOQUINOLINE 1,2,3 TRIAZOLE 1,3,5 TRIAZINE DERIVATIVE; 4 AMINOQUINOLINE 1,2,3 TRIAZOLE DERIVATIVE; 6 [[1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY) N2 (3,5 DIMETHOXYPHENYL) N4,N4 DIMETHYL 1,3,5 TRIAZINE 2,4 DIAMINE; 6 [[1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY] N2 (2,6 DIMETHYLPHENYL) N4,N4 DIMETHYL 1,3,5 TRIAZINE 2,4 DIAMINE; 6 [[1 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY] N2 (2,6 DIMETHYLPHENYL) N4,N4 DIMETHYL 1,3,5 TRIAZINE 2,4 DIAMINE; 6 [[1 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY] N2 (3,5 DIMETHOXYPHENYL) N4,N4 DIMETHYL 1,3,5 TRIAZINE 2,4 DIAMINE; 7 CHLORO QUINOLIN 4 YL [2 [4 (2,6 DICHLOROPHENOXYMETHYL) [1,2,3]TRIAZOL 1 YL] ETHYL]AMINE; 7 CHLORO QUINOLIN 4 YL[2 [4 (TETRAHYDRO PYRAN 2 YLOXYMETHYL) [1,2,3]TRIAZOL 1 YL]-ETHYL]AMINE; [1 [2 (7 CHLORO QUINOLIN 4 YLAMINO)ETHYL] 1H [1,2,3]TRIAZOL 4 YL]METHANOL; [1 [3 (7 CHLORO QUINOLIN 4 YLAMINO)PROPYL] 1H [1,2,3]TRIAZOL 4 YL]METHANOL; [2 [4 (4 BROMO PHENOXYMETHYL) [1,2,3]TRIAZOL 1 YL] ETHYL] (7 CHLORO QUINOLIN 4 YL)AMINE; [2 [4 (4 BUTYLAMINO 6 MORPHOLIN 4 YL [1,3,5]TRIAZIN 2 YLOXYMETHYL) [1,2,3]TRIAZOL 1 YL]ETHYL] (7 CHLOROQUINOLIN 4 YL)AMINE; [2 [4 (4 CHLORO 3 METHYL PHENOXYMETHYL) [1,2,3]TRIAZOL 1 YL] ETHYL] (7 CHLORO QUINOLIN 4 YL)AMINE; [2 [4 (4 CHLORO PHENOXYMETHYL) [1,2,3]TRIAZOL 1 YL]ETHYL] (7 CHLORO QUINOLIN 4 YL)AMINE; ANTIMALARIAL AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; IC 50; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; CERCOPITHECUS AETHIOPS; MAGNETIC RESONANCE SPECTROSCOPY; PLASMODIUM FALCIPARUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES; TRIAZOLES; VERO CELLS;

PLASMODIUM FALCIPARUM;

EID: 79958808891     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01115.x     Document Type: Article

References (45)

1. WHO (2009) World malaria report.
2. Ridley R.G. (2002) Medical need, scientific opportunity and the drive for antimalarial drugs. Nature;415:686-693.
3. Frevert U. (2004) Sneaking in through the back entrance: the biology of malaria liver stages. Trends Parasitol;20:417-424.
4. Loeb F., Clark W.M., Coatney G.R., Coggeshall L.T., Dieuaide F.R., Dochez A.R., Hankansson E.G., Marshall E.K. Jr, Marvel C.S., McCoy O.R., Sapero J.J., Sebrell W.H., Shannon J.A., Carden G.A. Jr. (1946) Activity of a new antimalarial agent, chloroquine (SN 7618) Statement Approved by the Board for Coordination of Malarial Studies. J Am Med Assoc;130:1069-1070.
5. Kouznetsov V.V., Gomez-Barrio A. (2009) Recent developments in the design and synthesis of hybrid molecules based on aminoquinoline ring and their antiplasmodial evaluation. Eur J Med Chem;44:3091-3113.
6. Kaur K., Jain M., Reddy R.P., Jain R. (2010) Quinolines and structurally related heterocycles as antimalarials. Eur J Med Chem;45:3245-3264.
7. Egan T.J. (2004) Haemozoin formation as a target for the rational design of new antimalarials. Drug Des Rev;1:93-110.
8. O'Neill P.M., Bray P.G., Hawley S.R., Ward S.A., Park B.K. (1998) 4-Aminoquinolines-past, present, and future: a chemical perspective. Pharmacol Ther;77:29-58.
9. Dechy-Cabaret O., Benoit-Vical F., 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. Robert A., Dechy-Cabaret O., Cazelles J., Meunier B. (2002) From mechanistic studies on Artemisinin derivatives to new modular antimalarial drugs. Acc Chem Res;35:167-174.
11. Meunier B. (2008) Hybrid molecules with a dual mode of action: dream or reality? Acc Chem Res;41:69-77.
12. Dechy-Cabaret O., Benoit-Vical F., Loup C., Robert A., Vial H., Gomitzka H., Bonhoure A., Magnaval J.F., Seguela J.P., Meunier B. (2004) Synthesis and antimalarial activity of trioxaquine derivatives. Chemistry;10:1625-1636.
13. Singh C., Malik H., Puri S.K. (2004) Synthesis and antimalarial activity of a new series of trioxaquines. Bioorg Med Chem;12:1177-1182.
14. Biot C., Glorian G., Maciejewski L.A., Brocard J.S. (1997) Synthesis and antimalarial activity in vitro and in vivo of a new Ferrocene-Chloroquine analogue. J Med Chem;40:3715-3718.
15. Chiyanzu I., Clarkson C., Smith P.J., Lehman J., Gut J., Rosenthal P.J., Chibale K. (2005) Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives. Bioorg Med Chem;13:3249-3261.
16. Gupta L., Srivastava K., Singh S., Puri S.K., Chauhan P.M.S. (2008) Synthesis of 2-[3-(7-Chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2, 3, 4, 9-tetrahydro-1H-β-carbolines as a new class of antimalarial agents. Bioorg Med Chem Lett;18:3306-3309.
17. Beagley P., Blackie M.A.L., Chibale K., Clarkson C., Meijboom R., Moss J.R., Smith P.J., Su H. (2003) Synthesis and antiplasmodial activity in vitro of new ferrocene-chloroquine analogues. Dalton Trans;15:3046-3051.
18. Musonda C.C., Gut J., Rosenthal P.J., Yardley V., Carvalho de Souza R.C., Chibale K. (2006) Application of multicomponent reactions to antimalarial drug discovery. Part 2: new antiplasmodial and antitrypanosomal 4-aminoquinoline γ- and δ-lactams via a 'catch and release' protocol. Bioorg Med Chem;14:5605-5615.
19. Domarle O., Blampain G., Agnaniet H., Nzadiyabi T., Lebibi J., Brocard J., Maciejewski L., Biot C., Georges A.J., Millet P. (1998) In vitro antimalarial activity of a new organometallic analog, ferrocene-chloroquine. Antimicrob Agents Chemother;42:540-544.
20. Melato S., Prosperi D., Coghi P., Basilico N., Monti D. (2008) A combinatorial approach to 2, 4, 6-trisubstituted triazines with potent antimalarial activity: combining conventional synthesis and microwave-assistance. ChemMedChem;3:873-876.
21. Kumar A., Srivastava K., Kumar S.R., Puri S.K., Chauhan P.M.S. (2008) Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents. Bioorg Med Chem Lett;18:6530-6533.
22. Sunduru N., Sharma M., Srivastava K., Rajakumar S., Puri S.K., Saxena J.K., Chauhan P.M.S. (2009) Synthesis of oxalamide and triazine derivatives as a novel class of hybrid 4-aminoquinoline with potent antiplasmodial activity. Bioorg Med Chem;17:6451-6462.
23. Manohar S., Khan S.I., Rawat D.S. (2010) Synthesis, antimalarial activity and cytotoxicity of 4-aminoquinoline-triazine conjugates. Bioorg Med Chem Lett;20:322-325.
24. Aher N.G., Pore V.S., Mishra N.N., Kumar A., Shukla P.K., Sharma A., Bhat M.K. (2009) Synthesis and antifungal activity of 1, 2, 3-triazole containing fluconazole analogues. Bioorg Med Chem Lett;19:759-763.
25. Demaray J.A., Thuener J.E., Dawjon M.N., Sucheck S.J. (2008) Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity. Bioorg Med Chem Lett;18:4868-4871.
26. Beena, Kumar N., Rohilla R.K., Roy N., Rawat D.S. (2009) Synthesis and antibacterial activity evaluation of metronidazole-triazole conjugates. Bioorg Med Chem Lett;19:1396-1398.
27. Tripathi R.P., Yadav A.K., Ajay A., Bisht S.S., Chaturvedi V., Sinha S.K. (2010) Application of Huisgen (3+2) cycloaddition reaction: synthesis of 1-(2, 3-dihydrobenzofuran-2-yl-methyl [1, 2, 3]-triazoles and their antitubercular evaluations. Eur J Med Chem;45:142-148.
28. Kolb H.C., Sharpless K.B. (2003) The growing impact of click chemistry on drug discovery. Drug Dis Tod;8:1128-1137.
29. Atheaya H., Khan S.I., Mamgain R., Rawat D.S. (2008) Synthesis, thermal stability, antimalarial activity of symmetrically and asymmetrically substituted tetraoxanes. Bioorg Med Chem Lett;18:1446-1449.
30. Kumar N., Khan S.I., Sharma M., Atheaya H., Rawat D.S. (2009) Iodine-catalyzed one-pot synthesis and antimalarial activity evaluation of symmetrically and asymmetrically substituted 3, 6-diphenyl[1, 2, 4, 5]tetraoxanes. Bioorg Med Chem Lett;19:1675-1677.
31. Kumar N., Khan S.I., Beena, Rajalakshmi G., Kumaradhas P., Rawat D.S. (2009) Synthesis, antimalarial activity and cytotoxicity of substituted 3, 6-diphenyl-[1, 2, 4, 5]tetraoxanes. Bioorg Med Chem;17:5632-5638.
32. Rawat D.S., Kumar N., Sharma M. Indian Patent Application No: 2103/DEL/2008.
33. Kumar N., Singh R., Rawat D.S. (2011) Tetraoxanes: synthetic and medicinal chemistry perspective. Med Res Rev; In press, doi:.
34. Burgess S.J., Selzer A., Kelly J.X., Smilkstein M.J., Riscoe M.K., Peyton D.H. (2006) A chloroquine-like molecule designed to reverse resistance in plasmodium falciparum. J Med Chem;49:5623-5625.
35. Egan T.J., Hunter R., Kaschula C.H., Marques H.M., Misplon A., Walden J. (2000) Structure-function relationships in aminoquinolines: effect of amino and chloro groups on Quinoline-Hematin complex formation, Inhibition of β-Hematin formation, and antiplasmodial activity. J Med Chem;43:283-291.
36. Bolte J., Demuynck C., Lhomme J. (1977) Synthetic models of DNA complexes with antimalarial compounds. 2. The problem of guanine specificity in chloroquine binding. J Med Chem;20:106-113.
37. de Souza M.V.N., Pais K.C., Kaiser C.R., Peralta M.A., de L Ferreira M., Lourenco M.C.S. (2009) Synthesis and in vitro antitubercular activity of a series of quinoline derivatives. Bioorg Med Chem;17:1474-1480.
38. Ishikawa T., Mizutani A., Miwa C., Oku Y., Komano N., Takami A., Watanabe T. (1997) Cesium fluoride-mediated claisen rearrangements of phenyl propargyl ethers: substituent effects of an ortho-alkoxy group on the benzene ring or modified propargyl residues. Heterocycles;45:2261-2272.
39. Pal M., Parasuraman K., Yeleswarapu K.R. (2003) Palladium-catalyzed cleavage of O/N-propargyl protecting groups in aqueous media under a Copper-free condition. Org Lett;5:349-352.
40. Joshi M.C., Joshi P., Rawat D.S. (2006) Microwave assisted synthesis of symmetrically and asymmetrically substituted acyclic enediynes. Arkivoc;16:65-74.
41. Musonda C.C., Whitlock G.A., Witty M.J., Brun R., Kaiser M. (2009) Synthesis and evaluation of 2-pyridyl pyrimidines with in vitro antiplasmodial and antileishmanial activity. Bioorg Med Chem Lett;19:401-405.
42. Zheng M., Xu C., Ma J., Sun Y., Du F., Liu H., Lin L., Li C., Ding J., Chen K., Jiang H. (2007) Synthesis and antitumor evaluation of a novel series of triaminotriazine derivatives. Bioorg Med Chem;15:1815-1827.
43. Jain M., Khan S.I., Tekwani B.L., Jacob M.R., Singh S., Singh P.P., Jain R. (2005) Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues. Bioorg Med Chem;13:4458-4466.
44. Makler M.T., Hinrichs D.J. (1993) Measurement of the lactate dehydrogenase activity of Plasmodium falciparum as an assessment of Parasitemia. Am J Trop Med Hyg;48:205-210.
45. Mustafa J., Khan S.I., Ma G., Walker L.A., Khan I.A. (2004) Synthesis and anticancer activities of fatty acid analogs of Podophyllotoxin. Lipids;39:167-172.