A new class of phenazines with activity against a chloroquine resistant plasmodium falciparum strain and antimicrobial activity

Journal of Medicinal Chemistry

Volumn 54, Issue 13, 2011, Pages 4913-4917

  Hussain, Hidayat ^a   Specht, Sabine ^b   Sarite, Salem R ^b   Saeftel, Michael ^b   Hoerauf, Achim ^b   Schulz, Barbara ^c   Krohn, Karsten ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

^b UNIVERSITY OF BONN   (Germany)

^c TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL; 2 NAPHTHOL; BENZO[A]PHENAZINE; CHLOROQUINE; PHENAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BRAIN MALARIA; DRUG SYNTHESIS; GROWTH INHIBITION; MOUSE; NONHUMAN; ONE POT SYNTHESIS; OXYGENATION; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; CHLOROQUINE; DRUG RESISTANCE; MALARIA, CEREBRAL; MICE; MICE, INBRED C57BL; PHENAZINES; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960182466     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200302d     Document Type: Article

References (16)

1. The World Health Report 1997; World Health Organization: Geneva, 1997.
2. Andrade-Neto, V. F.; Goulart, M. O. F.; Filho, J. F. S.; da Silva, M. J.; Pinto, M. C. F. R.; Pinto, A. V.; Zalis, M. G.; Carvalhoa, L. H.; Krettli, A. U. Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo Bioorg. Med. Chem. Lett. 2004, 14, 1145-1149 (Pubitemid 38229844)
3. Makgatho, M. E.; Anderson, R.; O'Sullivan, J. F.; Egan, T. J.; Freese, J. A.; Cornelius, N.; van Rensburg, C. E. J. Tetramethylpiperidine-substituted phenazines as novel anti-plasmodial agents Drug Dev. Res. 2000, 50, 195-202
4. Laursen, J. B.; Nielsen, J. Phenazine natural products: biosynthesis, synthetic analogues, and biological activity Chem. Rev. 2004, 104, 1663-1685
5. 2O]•Py•HMPT Chem. Ber. 1989, 122, 2323-2330
6. Krohn, K. Zirconium alkoxide catalyzed oxidation of phenols, alcohols, and amines Synthesis 1997, 1115-1127
7. Adam, H.; Khanbabaee, K.; Krohn, K.; Küpke, J.; Rieger, H.; Steingröver, K.; Vinke, I. Transition-Metal Alkoxide-Catalyzed Oxidation of Phenols, Alcohols, and Amines with tert -Butyl Hydroperoxide. In Peroxide Chemistry, Mechanistic and Preparative Aspects of Oxygen Transfer; Adam, W., Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 469-493.
8. Wanzlick, H.-W. Synthesen mit naszierenden Chinonen Angew. Chem. 1964, 76, 313-319
9. Angew. Chem., Int. Ed. Engl. 1964, 3, 401.
10. Mimoun, H.; Serre de Roch, I.; Sajus, L. Covalent peroxide complexes of molybdenum and tungsten with organic bases Bull. Soc. Chim. Fr. 1969, 1481-1492
11. Jones, P.; Villeneuve, G. B.; Fei, C.; DeMarte, J.; Haggarty, A. J.; Nwe, K. T.; Martin, D. A.; Lebuis, A. M.; Finkelstein, J. M.; Gour-Salin, B. J.; Chan, T. H.; Leyland-Jones, B. R. Synthesis and structure-activity relationships of 2-pyrazinylcarboxamidobenzoates and β-ionylideneacetamidobenzoates with retinoidal activity J. Med. Chem. 1998, 41, 3062-3077 (Pubitemid 28359942)
12. Jiang, C.-W. Syntheses, characterization and DNA binding of mono- and diruthenium(II) complexes containing 2,2′-bis(1,2,4-triazino[5,6- f ]phenanthren-3-yl)-4,4′-bipyridine and 2,2′-bipyridine ligands Inorg. Chim. Acta 2005, 358, 1231-1236 (Pubitemid 40260996)
13. Corey, E. J.; Lee, D.-H.; Sarshar, S. Convenient routes to symmetrical benzils and chiral 1,2-diaryl-l,2-diaminoethanes, useful controllers and probes for enantioselective synthesis Tetrahedron: Asymmetry 1995, 6, 3-6
14. Moloney, M. B.; Pawluk, A. R.; Ackland, N. R. Plasmodium falciparum growth in deep culture Trans. R. Soc. Trop. Med. Hyg. 1990, 84, 516-518 (Pubitemid 20266965)
15. Trager, W.; Williams, J. Extracellular (axenic) development in vitro of the erythrocytic cycle of Plasmodium falciparum Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5351-5355
16. Krohn, K.; Gehle, D.; Kamp, O.; van Ree, T. Highly deoxygenated sugars. II. Synthesis of chiral cyclopentenes via novel carbocyclization of C-4 branched deoxysugars J. Carbohydr. Chem. 2003, 22, 377-383 (Pubitemid 37412123)