Antimalarials based on the dioxane scaffold of plakortin. A concise synthesis and SAR studies

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 1, 2011, Pages 312-320

  Fattorusso, Caterina ^a   Persico, Marco ^a   Basilico, Nicoletta ^b   Taramelli, Donatella ^b   Fattorusso, Ernesto ^a   Scala, Fernando ^a   Taglialatela Scafati, Orazio ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Antimalarial; Endoperoxide; Knoevenagel reaction; Photooxygenation; Plakortin

Indexed keywords

ALKYL ARYL ETHER; ANTIMALARIAL AGENT; CHLOROQUINE; DIOXANE; ENDOPEROXIDE; PLAKORTIN; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; IC 50; NONHUMAN; PHARMACOPHORE; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANTIMALARIALS; DIOXANES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650748568     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.11.014     Document Type: Article

References (30)

1. R.W. Snow, C.A. Guerra, A.M. Noor, H.Y. Myint, and S.I. Hay Nature 434 2005 214
2. A.M. Dondorp, S. Yeung, L. White, C. Nguon, N.P. Day, D. Socheat, and L. von Seidlein Nat. Rev. Microbiol. 8 2010 272
3. http://www.MMV.org/IMG/pdf/PRODUCT-PROFILE-with-logo.pdf.
4. F. Cafieri, E. Fattorusso, O. Taglialatela-Scafati, and A. Ianaro Tetrahedron 55 1999 7045
5. E. Fattorusso, S. Parapini, C. Campagnuolo, N. Basilico, O. Taglialatela-Scafati, and D. Taramelli J. Antimicrob. Chemother. 50 2002 883
6. C. Campagnuolo, E. Fattorusso, A. Romano, O. Taglialatela-Scafati, N. Basilico, S. Parapini, and D. Taramelli Eur. J. Org. Chem. 2005 5077
7. C. Fattorusso, M. Persico, B. Calcinai, C. Cerrano, S. Parapini, D. Taramelli, E. Novellino, A. Romano, F. Scala, E. Fattorusso, and O. Taglialatela-Scafati J. Nat. Prod. 73 2010 1138
8. C. Fattorusso, G. Campiani, B. Catalanotti, M. Persico, N. Basilico, S. Parapini, D. Taramelli, C. Campagnuolo, E. Fattorusso, A. Romano, and O. Taglialatela-Scafati J. Med. Chem. 49 2006 7088
9. O. Taglialatela-Scafati, E. Fattorusso, A. Romano, F. Scala, V. Barone, P. Cimino, E. Stendardo, B. Catalanotti, M. Persico, and C. Fattorusso Org. Biomol. Chem. 8 2010 846
10. M. Matsumoto, and K. Kondo J. Org. Chem. 40 1975 2259
11. E.L. Clennan, and M.E. Mehrsheikh-Mohammadi J. Am. Chem. Soc. 105 1983 5932
12. M. Bobrowski, A. Liwo, S. Oldziej, D. Jeziorek, and T. Ossowski J. Am. Chem. Soc. 122 2000 8112
13. M. Matsumoto, and K. Kuroda Tetrahedron Lett. 23 1982 1285
14. N. Ragoussis, and V. Ragoussis J. Chem. Soc., Perkin Trans. 1 1998 3529
15. V. Ragoussis, M. Panopoulou, and N. Ragoussis J. Agric. Food Chem. 52 2004 5047
16. M.K. Schwaebe, and R.D. Little Tetrahedron Lett. 37 1996 6635
17. T.V. Robinson, D.K. Taylor, and E.R.T. Tiekink J. Org. Chem. 71 2006 7236
18. J.A. Kepler, A. Philip, Y.W. Lee, M.C. Morey, and F.I. Carroll J. Med. Chem. 31 1988 713
19. A.J. Bloodworth, and H.J. Eggelte J. Chem. Soc., Perkin Trans. 2 1984 2069
20. E. Bascetta, F.D. Gunstone, and C.M. Scrimgeour J. Chem. Soc., Perkin Trans 1 1984 2199
21. C.W. Jefford Curr. Med. Chem. 8 2001 1803
22. F. Freeman, H.N. Po, and W.J. Hehre J. Mol. Struct. (Theochem) 503 2000 145
23. F. Freeman, C. Lee, W.J. Hehre, and H.N. Po J. Comput. Chem. 18 1997 1392
24. J.R. Maple, M.J. Hwang, T.P. Stockfisch, U. Dinur, M. Waldman, C.S. Ewig, and A.T. Hagler J. Comput. Chem. 15 1994 162
25. R. Fletcher Unconstrained Optimization Practical Methods of Optimization Vol. 1 1980 John Wiley & Sons New York
26. J.J.P. Stewart J. Mol. Model. 13 2007 1173
27. MOPAC2009, James, J. P. Stewart, Stewart Computational Chemistry, Colorado Springs, CO, USA, http://OpenMOPAC.net, 2008.
28. J. Baker J. Comput. Chem. 7 1986 385
29. W. Trager, and J.B. Jensen Science 193 1976 673
30. M. Makler, and D. Hinrichs Am. J. Trop. Med. Hyg. 48 1993 205