Design and preparation of sterol mimetics as potential antiparasitics

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 20, 2010, Pages 7291-7301

  Gigante, Federica ^a   Kaiser, Marcel ^b,c   Brun, Reto ^b,c   Gilbert, Ian H ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Azasterol; Leishmania; Trypanosoma

Indexed keywords

ANTILEISHMANIAL AGENT; ANTIPARASITIC AGENT; ANTITRYPANOSOMAL AGENT; AZASTEROL DERIVATIVE; BENZIMIDAZOLE; MELARSOPROL; METHYL N 4 (4 ACETOXYMETHYLBENZAMIDYL) BENZYL 4 AMINOBUTANOATE; METHYL N 4 (4 ACETOXYMETHYLBENZAMIDYL) PHENETHYL 4 AMINOBUTANOATE; MILTEFOSINE; N (4 ACETOXYMETHYLPHENYL) 3 (2 OXOPYRROLIDIN 1 YL) METHYLPYRROLIDINE 1 CARBOXAMIDE; N (4 ACETOXYMETHYLPHENYL) 3 (N' 3 METHOXYCARBONYLPROPYL) AMINOMETHYLPYRROLIDINE 1 CARBOXAMIDE; N (4 ACETOXYMETHYLPHENYL) 3 HYDROXYMETHYLPYRROLIDINE 1 CARBOXAMIDE; N (4 ACETOXYMETHYLPHENYL) 3 N' 5 METHOXYCARBONYLPENT 1 YL) AMINOMETHYL PYRROLIDINE 1 CARBOXAMIDE; PODOPHYLLIN; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PHYSICAL CHEMISTRY; RAT;

ANILIDES; ANTIPARASITIC AGENTS; DRUG DESIGN; LEISHMANIA; MODELS, MOLECULAR; STEROLS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA CRUZI;

TRYPANOSOMA; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI;

EID: 77957598015     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.007     Document Type: Article

References (29)

1. K.D. Stuart, R. Brun, S.L. Croft, A. Fairlamb, R.E. Gurtler, J.H. McKerrow, S. Reed, and R. Tarleton J. Clin. Invest. 118 2008 1301
2. L. Gros, S.O. Lorente, C.J. Jimenez, V. Yardley, L. Rattray, H. Wharton, S. Little, S.L. Croft, L.M. Ruiz-Perez, D. Gonzalez-Pacanowska, and I.H. Gilbert J. Med. Chem. 49 2006 6094
3. L. Gros, V.M. Castillo-Acosta, C.J. Jimenez, M. Sealey-Cardona, S. Vargas, A.M. Estevez, V. Yardley, L. Rattray, S.L. Croft, L.M. Ruiz-Perez, J.A. Urbina, I.H. Gilbert, and D. Gonzalez-Pacanowska Antimicrob. Agents Chemother. 50 2006 2595
4. S.O. Lorente, C.J. Jimenez, L. Gros, V. Yardley, K. de Luca-Fradley, S.L. Croft, J.A. Urbina, L.M. Ruiz-Perez, D.G. Pacanowska, and I.H. Gilbert Bioorg. Med. Chem. 13 2005 5435
5. S.O. Lorente, J.C.F. Rodrigues, C.J. Jimenez, M. Joyce-Menekse, C. Rodrigues, S.L. Croft, V. Yardley, K. de Luca-Fradley, L.M. Ruiz-Perez, J. Urbina, W. de Souza, D.G. Pacanowska, and I.H. Gilbert Antimicrob. Agents Chemother. 48 2004 2937
6. F. Magaraci, C.J. Jimenez, C. Rodrigues, J.C.F. Rodrigues, M.V. Braga, V. Yardley, K. de Luca-Fradley, S.L. Croft, W. de Souza, L.M. Ruiz-Perez, J. Urbina, D.G. Pacanowska, and I.H. Gilbert J. Med. Chem. 46 2003 4714
7. F. Gigante, M. Kaiser, R. Brun, and I.H. Gilbert Bioorg. Med. Chem. 17 2009 5950
8. A.C. Oehlschlager, and E.K. Czyzewska Emerging Targets in Antibacterial and Antifungal Chemotherapy 1992 Chapman & Hall New York p 437
9. M.A. Ator, S.J. Schmidt, J.L. Adams, and R.E. Dolle Biochemistry 28 1989 9633
10. A. Rahier, J.C. Genot, F. Schuber, P. Benveniste, and A.S. Narula J. Biol. Chem. 259 1984 5215
11. A. Rahier, M. Taton, P. Bouviernave, P. Schmitt, P. Benveniste, F. Schuber, A.S. Narula, L. Cattel, C. Anding, and P. Place Lipids 21 1986 52
12. A. Rahier, M. Taton, and P. Benveniste Biochem. Soc. Trans. 18 1990 48
13. I. Coppens, and P.J. Courtoy Annu. Rev. Microbiol. 54 2000 129
14. I. Coppens, and P.J. Courtoy Mol. Biochem. Parasitol. 73 1995 179
15. S.W. Landvatter, and J.A. Katzenellenbogen Mol. Pharmacol. 20 1981 43
16. E. Bridgeman, J.L. Cavill, D.J. Schofield, D.S. Wilkins, and N.C.O. Tomkinson Tetrahedron Lett. 46 2005 8521
17. K.S. Korach Mol. Struct. Biol. Act. Steroids 1992 209
18. B.R. Sadler, S.J. Cho, K.S. Ishaq, K. Chae, and K.S. Korach J. Med. Chem. 41 1998 2261
19. D.J. Grainger, and J.C. Metcalfe Nat. Med. 2 1996 381
20. E. Bridgeman, and N.C.O. Tomkinson Synlett 2006 243
21. D. HobbsMallyon, W. Li, and D.A. Whiting J. Chem. Soc., Perkin Trans. 1 1997 1511
22. K.S. Korach, P. Sarver, K. Chae, J.A. McLachlan, and J.D. McKinney Mol. Pharmacol. 33 1988 120
23. D. Lesuisse, E. Albert, F. Bouchoux, E. Cerede, J.M. Lefrancois, M.O. Levif, S. Tessier, B. Tric, and G. Teutsch Bioorg. Med. Chem. Lett. 11 2001 1709
24. Y. Hashimoto, and H. Miyachi Bioorg. Med. Chem. 13 2005 5080
25. P.R. Gerber, and K. Muller J. Comput. Aided Mol. Des. 9 1995 251
26. P.D. Bailey An Introduction to Peptide Chemistry 1990 Wiley Medical Publication Chichester A
27. R.A. Fernandes, and P. Kumar Tetrahedron Lett. 44 2003 1275
28. T. Wenzler, D.W. Boykin, M.A. Ismail, J.E. Hall, R.R. Tidwell, and R. Brun Antimicrob. Agents Chemother. 53 2009 4185
29. S. Ganapaty, P.S. Thomas, G. Karagianis, P.G. Waterman, and R. Brun Phytochemistry 67 2006 1950