Synthesis of 6(α,β)-aminocholestanols as ergosterol biosynthesis inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 24, 1998, Pages 3627-3630

  Beuchet, Pierre ^a   El Kihel, Laïla ^a   Dherbornez, Michel ^a   Charles, Georges ^a   Letourneux, Yves ^a  

^a UNIVERSITÉ DE LA ROCHELLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

6ALPHA AMINOCHOLESTANOL; 6BETA AMINOCHOLESTANOL; ANTIFUNGAL AGENT; CHOLESTANOL; ERGOSTEROL; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; CANDIDA; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME MECHANISM; HOSPITAL INFECTION; MYCOSIS; PNEUMOCYSTIS CARINII; STEROL SYNTHESIS;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; CHOLESTANOLS; ERGOSTEROL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SACCHAROMYCES CEREVISIAE;

ASPERGILLUS; CANDIDA; FUNGI; PNEUMOCYSTIS CARINII;

EID: 0032535173     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00661-1     Document Type: Article

References (23)

1. 1. Oehslanger, A. C. ; Angus, R. H. ; Pierce, A. M. ; Pierce, H. D. ; Srinivasan, R. Biochemistry 1984, 3582.
2. 2. Berg, D. ; Plempel, M. ; J. Enzym. Inhib. 1989, 3, N°1, 1. Georgopapadakou, N. H. ; Walsh, T. J., Science. 1994, 264, 371.
3. 2. Berg, D. ; Plempel, M. ; J. Enzym. Inhib. 1989, 3, N°1, 1. Georgopapadakou, N. H. ; Walsh, T. J., Science. 1994, 264, 371.
4. 3. Nes, D. ; Xu, S. ; Parish, E. J. Arch. Biochem. Biophys. 1989, 2, 323.
5. 4. Taton, M. ; Benveniste, P. ; Rahier, A. Pestic. Sci., 1987, 269.
6. 5. El kihel, L. ; Soustre, I. ; Karst, F. Letourneux, Y. F.E.M.S. 1994, 120, 163.
7. 6. Bimpson, T. ; Goad, L. ; Goodwin, T. W. J. Chem. Soc., Chem. Commun. 1969, 297. Topham, R. W. ; Frieden, E. J. Biol Chem. 1970, 245, 2319. Fryberg, M. ; Oehslanger, A. C. ; Unrau, A. M. Biochem. Biophys. Res. Commun. 1973, 51, N°1, 219.
8. 6. Bimpson, T. ; Goad, L. ; Goodwin, T. W. J. Chem. Soc., Chem. Commun. 1969, 297. Topham, R. W. ; Frieden, E. J. Biol Chem. 1970, 245, 2319. Fryberg, M. ; Oehslanger, A. C. ; Unrau, A. M. Biochem. Biophys. Res. Commun. 1973, 51, N°1, 219.
9. 6. Bimpson, T. ; Goad, L. ; Goodwin, T. W. J. Chem. Soc., Chem. Commun. 1969, 297. Topham, R. W. ; Frieden, E. J. Biol Chem. 1970, 245, 2319. Fryberg, M. ; Oehslanger, A. C. ; Unrau, A. M. Biochem. Biophys. Res. Commun. 1973, 51, N°1, 219.
10. 7. Arthington, B. A. ; Benett, L.G. ; Skatraud, P. C. ; Guynn, C. J. ; Barbuch, R. J. ; Upbright, C. E. ; Bard, M. Gene, 1991, 102, 39.
11. 8. Rodriguez, R. J. ; Parks, L. W. Arch. Biochem. Biophys. 1983, 225, 861.
12. 9. Goldstein, A. S. ; Frye, L. L. J. Med. Chem. 1996, 39, 5092.
13. 10. Agnostopoulos, L. E. ; Fieser, L.F. J. Am. Chem. Soc. 1954, 76, 532.
14. +) ; 413 (44) ; 396 (72) ; 383 (60) ; 329 (25) ; 300 (100).
15. 12. Defaye, G. ; Fétizon, M. Bull. Soc. Chim. Fr. 1969, 5, 1632.
16. +.) ; 386 (7) ; 273 (3) ; 255 (3) ; 248 (100) ; 155 (6).
17. 14. Bull, J. R. ; Jones, R. H. ; Meakins, G. D. J. Chem. Soc. 1965, 2601.
18. 2).
19. -1) : 3600-3200 (OH) ; 1545, 1372(N=O). mp = 102°C.
20. -1) : 3600-3200 (OH); 1547, 1370 (N=O). mp =102-104°C.
21. -1) : 3600-3200 (OH) ; 1660 (NH-CO). mp = 256°C.
22. -1) : 3600-3200 (OH) ; 1665 (NH-CO). mp = 250°C.
23. 20. The fungal growths were measured in vitro using a liquid-phase turbimetric system (Bioscreen®, from Labsystem, France) and automatically evaluated every 30 minutes for 24 hours using various concentrations of drugs. Dei-Cas, E. ; Dujardin, L. ; Ribeiro Pinto, M. E. ; Ajana, F. ; Fruit, J. ; Poulain, D. ; Camus, D. ; Vernes, A. Mycoses, 1991, 34, 167.