Amodiaquine analogues containing NO-donor substructures: Synthesis and their preliminary evaluation as potential tools in the treatment of cerebral malaria

European Journal of Medicinal Chemistry

Volumn 46, Issue 5, 2011, Pages 1757-1767

  Bertinaria, Massimo ^a   Guglielmo, Stefano ^a   Rolando, Barbara ^a   Giorgis, Marta ^a   Aragno, Cristina ^a   Fruttero, Roberta ^a   Gasco, Alberto ^a   Parapini, Silvia ^b   Taramelli, Donatella ^b   Martins, Yuri C ^c   Carvalho, Leonardo J M ^c  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

^c LA JOLLA BIOENGINEERING INSTITUTE   (United States)

Author keywords

Amodiaquine; Cerebral malaria; Furoxans; Nitric oxide; Nitrooxy derivatives

Indexed keywords

1 [2 (NITROOXY)ETHYL]PIPERAZIN 4 IUM NITRATE; 1 [3 (NITROOXY)ETHYL]PIPERAZIN 4 IUM NITRATE; 4 [(7 CHLOROQUINOLIN 4 YL)AMINO] 2 [[[[[2 (3 PHENYLSULFONYLFUROXAN 4 YL)OXY]ETHYL]ETHYL]AMINO]METHYL]PHENOL; 4 [(7 CHLOROQUINOLIN 4 YL)AMINO] 2 [[[ETHYL[2 (3 PHENYLFUROXAN 4 YL)OXY]ETHYL]AMINO]METHYL]PHENOL; 4 [(NITROOXY)METHYL]PIPERIDINIUM NITRATE; 4 [2 (NITROOXY)ETHYL]PIPERIDINIUM NITRATE; 6 [[5 [(7 CHLOROQUINOLIN 4 YL)AMINO] 2 HYDROXYBENZYL](ETHYL)AMINO]HEXAN 1,2 DIYLDINITRATE; 7 CHLORO 4 [[3 [[ETHYL [3 (NITROOXY)PROPYL]AMMONIO]METHYL]PHENYL]AMINO]QUINOLINIUM; 7 CHLORO 4 [[3 [[ETHYL [6 (NITROOXY)PROPYL]AMMONIO]METHYL]PHENYL]AMINO]QUINOLINIUM; 7 CHLORO 4 [[4 HYDROXY 3 [[4 [(NITROOXY)METHYL]PIPERIDINIUM 1 YL]METHYL]PHENYL]AMINO]QUINOLINIUM; 7 CHLORO 4 [[4 HYDROXY 3 [[4 [2 (NITROOXY)ETHYL]PIPERAZINE DIIUM 1 YL]METHYL]PHENYL]AMINO]QUINOLINIUM; 7 CHLORO 4 [[4 HYDROXY 3 [[4 [2 (NITROOXY)ETHYL]PIPERIDINIUM 1 YL]METHYL]PHENYL]AMINO]QUINOLINIUM; 7 CHLORO 4 [[4 HYDROXY 3 [[4 [3 (NITROOXY)PROPYL]PIPERAZINE DIIUM 1 YL]METHYL]PHENYL]AMINO]QUINOLINIUM; 7 CHLORO 4 [[4 HYDROXY 3 [[[3 (NITROOXY)PROPYL]AMMONIO]METHYL]PHENYL]AMINO]QUINOLINIUM; AMODIAQUINE; AMODIAQUINE DERIVATIVE; ANTIMALARIAL AGENT; CHLOROQUINE; N ETHYL 5,6 BIS(NITROOXY)HEXAN 1 AMMONIUM NITRATE; N ETHYL 6 (NITROOXY)HEXAN 1 AMMONIUM NITRATE; NITRIC OXIDE DONOR; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIMALARIAL DRUG RESISTANCE; ANTIMALARIAL DRUG SUSCEPTIBILITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; BRAIN MALARIA; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG POTENCY; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; RAT; SURVIVAL; VASODILATATION;

AMODIAQUINE; ANIMALS; ANTIPROTOZOAL AGENTS; AORTA, THORACIC; CHEMISTRY, PHYSICAL; MALARIA, CEREBRAL; MALE; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; NITRIC OXIDE DONORS; OXADIAZOLES; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; RATS; RATS, WISTAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79953178566     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.02.029     Document Type: Article

References (35)

1. World Malaria Report World Health Organisation 2008 Geneva, 2008
2. J. Loscalzo, J.A. Vita, Nitric Oxide and Cardiovascular System 2000 Humana Press Totowa
3. J.V. Esplugues Br. J. Pharmacol. 135 2002 1079 1095
4. C. Bogdan Nat. Immunol. 2 2001 907 916
5. A. Clark, and W.C. Cowden Pharmacol. Ther. 99 2003 221 260
6. K.K. Rockett, M.M. Awburn, W.B. Cowden, and I.A. Clark Infect. Immun. 59 1991 3280 3283
7. A. Sharma, A. Eapen, and S.K. Subbarao J. Biochem. 136 2004 329 334
8. U. Galli, L. Lazzarato, M. Bertinaria, G. Sorba, A. Gasco, S. Parapini, and D. Taramelli Eur. J. Med. Chem. 40 2005 1335 1340
9. P. Sobolewski, I. Gramaglia, J. Frangos, M. Intaglietta, and H.C. Van der Heyde Trends Parasitol. 21 2005 415 422
10. I. Gramaglia, P. Sobolewski, D. Meays, R. Contreras, J.P. Nolan, J.A. Frangos, M. Intaglietta, and H.C. Van der Heyde Nat. Med. 12 2006 1417 1422
11. T.W. Yeo, D.A. Lampah, R. Gitawati, E. Tjitra, E. Kenangalem, Y.R. McNeil, C.J. Darcy, D.L. Granger, J.B. Weinberg, B. Lopansri, R.N. Price, S.B. Duffull, D.S. Celermajer, and N.M. Anstey J. Exp. Med. 204 2007 2693 2704
12. P.J. Rosenthal, Antimalarial Chemotherapy 2001 Humana Press Totowa, New Jersey
13. World Health Organisation, WHO Model List of Essential Medicines. http://www.who.int revised on March 2005.
14. A. Gasco, R. Fruttero, and B. Rolando Mini Rev. Med. Chem. 5 2005 217 229
15. W. Kurosawa, T. Kan, and T. Fukuyama Org. Synth. 79 2002 186
16. S. Guglielmo, M. Bertinaria, B. Rolando, M. Crosetti, R. Fruttero, V. Yardley, S.L. Croft, and A. Gasco Eur. J. Med. Chem. 44 2009 5071 5079
17. R. Fruttero, G. Sorba, G. Ermondi, M. Lolli, and A. Gasco Farmacognosia 52 1997 405 410
18. D.C. Warhurst, J.C.P. Steele, I.S. Adagu, J.C. Craig, and C. Cullander J. Antimicrob. Chemother. 52 2003 188 193
19. P. Cabrales, G.M. Zanini, D. Meays, J.A. Frangos, and L.J. Carvalho Am. J. Pathol. 176 2010 1306 1315
20. P. Cabrales, G.M. Zanini, D. Meays, J.A. Frangos, L.J. Carvalho, J. Infect. Dis. (in press).
21. G. Sorba, G. Ermondi, R. Fruttero, U. Galli, and A. Gasco J. Heterocycl. Chem. 33 1996 327 334
22. L.B. Romanova, M.E. Ivanova, D.A. Nesterenko, and L.T. Ermenenko Russ. Chem. Bull. 43 1994 1207 1209
23. W.V. Farrar J. Chem. Soc. 1964 904 906
24. G. Sorba, C. Medana, R. Fruttero, C. Cena, A. Di Stilo, U. Galli, and A. Gasco J. Med. Chem. 40 1997 463 469
25. R.R. Ranatunge, M.E. Augustyniak, V. Dhawan, J.L. Ellis, D.S. Garvey, D.R. Janero, L.G. Letts, S.K. Richardson, M.J. Shumway, A.M. Trocha, D.V. Young, and I.S. Zemtseva Bioorg. Med. Chem. 14 2006 2589 2599
26. P.G. Baraldi, R. Romagnoli, M. del Carmen Nuñez, M. Perretti, M.J. Paul-Clark, M. Ferrario, M. Govoni, F. Benedini, and E. Ongini J. Med. Chem. 47 2004 711 719
27. H. Xubo, K.Y. Nguyen, V.C. Jiang, D. Lofland, H.E. Moser, and D. Pei J. Med. Chem. 47 2004 4941 4949
28. K.J. Fraunhoffer, D.A. Bachovchin, and M.C. White Org. Lett. 7 2005 223 226
29. T. Brown, N.J. Gibson, WO/1999/045017.
30. M.L. Fontane, H. Bazin, and R. Téoule Bioconjug. Chem. 4 1993 380 385
31. E.F. Elslager, S.C. Perricone, and F.H. Tendick J. Med. Chem. 12 1969 965 969
32. A. Avdeef, J.E.A. Comer, and S.J. Thomson Anal. Chem. 65 1993 42 49
33. W. Trager, and J.B. Jensen Science 193 1976 673 675
34. M. Makler, and D. Hinrichs Am. J. Trop. Med. Hyg. 48 2 1993 205 210
35. D. Monti, N. Basilico, S. Parapini, E. Pasini, P. Olliaro, and D. Taramelli FEBS Lett. 522 2002 3 5