Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for cholesterol ester hydrolase

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 14, 1996, Pages 1673-1676

  David, Béatrice ^a   Schuber, Francis ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL ESTERASE; ENZYME INHIBITOR; KETONE; ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; REACTION ANALYSIS;

EID: 0030598661     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00290-9     Document Type: Article

References (21)

1. 1. (a) Rudd, E.A.; Brockman, H.L. Lipases; Borström, B; Brockman, H.L. Eds.; Elsevier: Amsterdam, 1984, pp. 158-204.
2. (b) Heider, J.G. Pharmacological Control of Hyperlipidaemia; J.RProus Science Publishers, 1986; pp. 423-437.
3. 2. (a) Gelb, M.H.; Svaren, J.P.; Abeles, R.H. Biochemistry 1985, 24, 1813.
4. (b) Parisi, M.; Abeles, R.H. Biochemistry 1992, 31, 9429. Reviews:
5. (c) Imperiali, B. Synthetic Peptides in Biotechnology, A.R. Liss, Inc., 1988; pp 97-129.
6. (d) Medhi, S. Bioorg. Chem. 1993, 21, 249.
7. 3. (a) Gelb, M.H. J. Am. Chem. Soc. 1986, 108, 3146.
8. (b) Yuan, W.; Berman, R.J.; Gelb, M.H. J. Am. Chem. Soc, 1987, 109, 8071.
9. 4. (4aS)-4,4a,5,6,7,8-Hexahydro-4aβ-methyl-2(3H)-naphtalenone (commercial or prepared according to Pfau, M.; Revial G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273) was transformed into (4aS,8aR)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ-methyl-2(3H)-naphtalenone with lithium in ethylenediamine according to Hodge-Markgraf, J; Waugh-Staley, S.; Allen; T. Syn. Commun. 1989, 19, 1471.
10. 4. (4aS)-4,4a,5,6,7,8-Hexahydro-4aβ-methyl-2(3H)-naphtalenone (commercial or prepared according to Pfau, M.; Revial G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273) was transformed into (4aS,8aR)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ-methyl-2(3H)-naphtalenone with lithium in ethylenediamine according to Hodge-Markgraf, J; Waugh-Staley, S.; Allen; T. Syn. Commun. 1989, 19, 1471.
11. 5. Nicolaou, K.C.; Magolda, R.L.; Claremon, D.A. J. Am. Chem. Soc. 1980, 102, 1404.
12. + (23%).
13. 7. (a) Jones, D.M.; Wood, N.F. J. Chem. Soc. 1964, 5400.
14. (b) Ward, D.E; Rhee, C.K. Syn. Commun. 1988, 18, 1927.
15. (c) Ward, D.E; Rhee, C.K. Can. J. Chem. 1989, 67, 1206.
16. 8. (a) Lee, J.B., Nolan, T.J. Can. J. Chem. 1966, 44, 1331.
17. (b) Axelrod, E.M.; Milne, G.M.; Van Tamelen, E.E. J. Am. Chem. Soc. 1970, 92, 2131.
18. 9. Corey, E.J.; Erickson, B.W. J. Org. Chem. 1971, 36, 3553.
19. (b) Eliel, E.L.; Hartmann, A.A. J. Org. Chem. 1972, 37, 505.
20. 10. Meyers, A.I.; Sturgess, M.A. Tet. Lett. 1988, 29, 5339.
21. 14C]oleate as substrates.