Novel 4-aminoquinoline-pyrimidine based hybrids with improved in vitro and in vivo antimalarial activity

ACS Medicinal Chemistry Letters

Volumn 3, Issue 7, 2012, Pages 555-559

  Manohar, Sunny ^a   Rajesh, U Chinna ^a   Khan, Shabana I ^b,c   Tekwani, Babu L ^b,c   Rawat, Diwan S ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

4 aminoquinoline; antimalarial; pyrimidine

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; 4 AMINOQUINOLINE PYRIMIDINE DERIVATIVE; ANTIMALARIAL AGENT; ARTEMISININ; CHLOROQUINE; DOXORUBICIN; PYRIMETHAMINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ANTIMALARIAL DRUG RESISTANCE; ANTIMALARIAL DRUG SUSCEPTIBILITY; ARTICLE; CELL ASSAY; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DISEASE MODEL; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PLASMODIUM BERGHEI INFECTION; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; X RAY ANALYSIS;

PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

EID: 84863812396     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3000808     Document Type: Article

References (30)

1. Beckera, K.; Hua, Y.; Biller-Andorno, N. Infectious diseases: A global challenge Int. J. Med. Microbiol. 2006, 296, 179-185
2. WHO. World Malaria Report; WHO: Geneva, Switzerland, 2009.
3. Ridley, R. J. Medical need, scientific opportunity and the drive for antimalarial drugs Nature 2002, 415, 686-693
4. Kumar, N.; Singh, R.; Rawat, D. S. Tetraoxanes: Synthetic and medicinal chemistry perspective Med. Res. Rev. 2012, 32, 581-610
5. Kouznetsov, V. V.; Gomez-Barrio, A. Recent developments in the design and synthesis of hybrid molecules based on aminoquinoline ring and their antiplasmodial evaluation Eur. J. Med. Chem. 2009, 44, 3091-3113
6. Dondorp, A. M.; Norsten, F.; Yi, P.; Das, D.; Phyo, A. P.; Tarning, J.; Lwin, K. M.; Ariey, F.; Hanpithithakpong, W.; Lee, S. J.; Ringwald, P.; Silamut, K.; Imwong, M.; Chotivanich, K.; Lim, P.; Herdman, T.; An, S. S.; Yeung, S.; Singhasivanon, P.; Day, N. P. J.; Lindegardh, N.; Socheat, D.; White, N. J. Artemisinin resistance in Plasmodium falciparum malaria N. Engl. J. Med. 2009, 361, 455-467
7. Bloland, P. B.; Ettling, M.; Meek, S. Combination therapy for malaria in Africa: hype or hope? Bull. World Health Org. 2000, 78, 1378-1388
8. Robert, A.; Dechy-Cabaret, O.; Cazelles, J.; Meunier, B. From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs Acc. Chem. Res. 2002, 35, 167-174
9. Meunier, B. Hybrid molecules with a dual mode of action: Dream or reality? Acc. Chem. Res. 2008, 41, 69-77
10. Dechy-Cabaret, O.; Benoit-Vical, F.; Robert, A.; Meunier, B. Preparation and antimalarial activities of trioxaquines, new modular molecules with a trioxane skeleton linked to a 4-aminoquinoline ChemBioChem 2000, 1, 281-283
11. Manohar, S.; Khan, S. I.; Rawat, D. S. Synthesis, antimalarial activity and cytotoxicity of 4-aminoquinoline-triazine conjugates Bioorg. Med. Chem. Lett. 2010, 20, 322-325
12. Manohar, S.; Khan, S. I.; Rawat, D. S. Synthesis of 4-aminoquinoline-1,2, 3-triazole and 4-aminoquinoline-1,2,3-triazole-1,3,5-triazine hybrids as potential antimalarial agents Chem. Biol. Drug Des. 2011, 78, 124-136
13. Chiyanzu, I.; Clarkson, C.; Smith, P. J.; Lehman, J.; Gut, J.; Rosenthal, P. J.; Chibale, K. Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives Bioorg. Med. Chem. 2005, 13, 3249-3261
14. Biot, C.; Glorian, G.; Maciejewski, L. A.; Brocard, J. S. Synthesis and antimalarial activity in vitro and in vivo of a new Ferrocene-Chloroquine analogue J. Med. Chem. 1997, 40, 3715-3718
15. Wenzel, N. I.; Chavain, N.; Wang, Y.; Friebolin, W.; Maes, L.; Pradines, B.; Lanzer, M.; Yardley, V.; Brun, R.; Herold-Mende, C.; Biot, C.; Toth, K.; Davioud-Charvet, E. Antimalarial versus cytotoxic properties of dual drugs derived from 4-aminoquinolines and mannich bases: Interaction with DNA J. Med. Chem. 2010, 53, 3214-3226
16. Hargreaves, S. L.; Pilkington, B. L.; Russell, S. E.; Worthington, P. A. The synthesis of substituted pyridylpyrimidine fungicides using palladiumcatalysed cross-coupling reactions Tetrahedron Lett. 2000, 41, 1653-1656
17. Li, Y. X.; Luo, Y. P.; Xi, Z.; Niu, C. W.; He, Y. Z.; Yang, G. F. Design and syntheses of novel phthalazin-1(2H)-one derivatives as acetohydroxyacid synthase inhibitors J. Agric. Food Chem. 2006, 54, 9135-9139
18. Regnier, G.; Canevar, L.; Le, R. J.; Douarec, J. C.; Halstop, S.; Daussy, J. Triphenylpropylpiperazine derivatives as new potent analgetic substances J. Med. Chem. 1972, 15, 295-301
19. Sondhi, S. M.; Singh, N.; Johar, M.; Kumar, A. Synthesis, anti-inflammatory and analgesic activities evaluation of some mono, bi and tricyclic pyrimidine derivatives Bioorg. Med. Chem. 2005, 13, 6158-6166
20. Carlos, M. G.; John, R. M.; Charles, D. Nucleoside analogues and nucleobases in cancer treatment Lancet Oncol. 2002, 3, 415-424
21. Martyn, D. C.; Nijjar, A.; Celatka, C. A.; Mazitschek, R.; Cortese, J. F.; Tyndall, E.; Liu, H.; Fitzgerald, M. M.; ÒShea, T. J.; Danthi, S.; Clardy, J. Bioorg. Med. Chem. Lett. 2010, 20, 228-231
22. Qingyun, R.; Xiaosong, T.; Hongwu, H. Efficient synthesis of fused pyrimidine derivatives with biological activity via aza-wittig reaction Curr. Org. Synth. 2011, 8, 752-763
23. Delfino, R. T.; Santos-Filho, O. A.; Figueroa-Villar, J. D. Type 2 antifolates in the chemotherapy of falciparum malaria J. Braz. Chem. Soc. 2002, 13, 727-741
24. Atheaya, H.; Khan, S. I.; Mamgain, R.; Rawat, D. S. Synthesis, thermal stability, antimalarial activity of symmetrically and asymmetrically substituted tetraoxanes Bioorg. Med. Chem. Lett. 2008, 18, 1446-1449
25. Kumar, N.; Khan, S. I.; Beena; Rajalakshmi, G.; Kumaradhas, P.; Rawat, D. S. Synthesis, antimalarial activity and cytotoxicity of substituted 3,6-diphenyl-[1,2,4,5]tetraoxanes Bioorg. Med. Chem. 2009, 17, 5632-5638
26. Kumar, N.; Khan, S. I.; Atheaya, H.; Mamgain, R.; Rawat, D. S. Iodine-catalyzed one-pot synthesis and antimalarial activity evaluation of symmetrically and asymmetrically substituted 3,6-diphenyl[1,2,4,5]tetraoxanes Eur. J. Med. Chem. 2011, 46, 2816-2827
27. Sharma, M.; Chaturvedi, V.; Manju, Y. K.; Bhatnagar, S.; Srivastava, K.; Puri, S. K.; Chauhan, P. M. S. Substituted quinolinyl chalcones and quinolinyl pyrimiines as a new class of anti-infective agents Eur. J. Med. Chem. 2009, 44, 2081-2091
28. Rawat, D. S.; Manohar, S.; Rajesh, U. C. Aminoquinoline based hybrids and uses thereof. Indian Patent Application No. 661/DEL/2012.
29. Natarajan, J. K.; Alumasa, J. N.; Yearick, K.; Ekoue-Kovi, K. A.; Casabianca, L. B.; de Dios, A. C.; Wolf, C.; Roepe, P. D. 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. 2008, 51, 3466-3479
30. Jain, M.; Khan, S. I.; Tekwani, B. L.; Jacob, M. R.; Singh, S.; Singh, P. P.; Jain, R. Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues Bioorg. Med. Chem. 2005, 13, 4458-4466