Synthesis and study of a lipophilicα-keto amide inhibitor of pancreatic lipase

Organic Letters

Volumn 2, Issue 3, 2000, Pages 347-350

  Chiou, Antonia ^a   Markidis, Theodoros ^a   Constantinou Kokotou, Violetta ^b   Verger, Robert ^c   Kokotos, George ^a  

^a UNIVERSITY OF ATHENS   (Greece)

^b AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^c UPR 9025   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ENZYME INHIBITOR; KETONE; LIPID; PANCRELIPASE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; ENZYMOLOGY; IC 50; LIPID METABOLISM; PANCREAS; SURFACE PROPERTY; SYNTHESIS;

AMIDES; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; KETONES; LIPASE; LIPID METABOLISM; LIPIDS; PANCREAS; PANCRELIPASE; SURFACE PROPERTIES;

EID: 0034628223     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991295s     Document Type: Article

References (34)

1. Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. 1998, 37, 1608.
2. Reetz, M. T.; Jaeger, K.-E. Top. Curr. Chem. 1999, 200, 31.
3. (a) Carrière, F.; Barrowman, J. A.; Verger, R.; Laugier, R. Gastroenterology 1993, 105, 876.
4. (b) Lowe, M. E. Gastmenterology 1994, 107, 1524.
5. (a) Drent, M. L.; Vanderveen, E. A. Int. J. Obesity 1993, 17, 241.
6. (b) Thomson, A. B. R.; De Pover, A.; Keelan, M.; Jarocka-Kyrta, E.; Clandinin, M. T. Methods Enzymol. 1997, 286, 3.
7. For reviews, see: (a) Gargouri, Y.; Ransac, S.; Verger, R. Biochim. Biophys. Acta 1997, 1344, 6.
8. (b) Ransac, S.; Gargouri, Y.; Marguet, F.; Buono, G.; Beglinger, C.; Hildebrand, P.; Lengsfeld, H.; Hadvary, P.; Verger, R. Methods Enzymol. 1997, 286, 191.
9. Guidoni, A.; Benkouka, F.; de Caro, J.; Rovery, M. Biochim. Biophys. Acta 1981, 660, 148.
10. Lowe, M. E. J. Biol. Chem. 1992, 267, 17069.
11. (a) Winkler, F. K.; D'Arcy, A.; Hunziker, W. Nature 1990, 343, 771.
12. (b) Brady, L.; Brzozowski, A. M.; Derewenda, Z. S.; Dodson, E.; Dodson, G.; Tolley, S.; Turkenburg, J. P.; Christiansen, L.; Hughe-Jensen, B.; Norskov, L.; Thim, L.; Menge, U. Nature 1990, 343, 767.
13. van Tilbeurgh, H.; Egloff, M.-P.; Martinez, C.; Rugani, N.; Verger, R.; Cambillau, C. Nature 1993, 362, 814.
14. (a) Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760.
15. (b) Beugue, J.-P.; Bonnet-Delpon, D. Tetrahedron 1991, 47, 3207.
16. Li, Z.; Patil, G. S.; Colubski, Z. E.; Hori, H.; Tehran, K.; Foreman, J. E.; Eveleth, D. D.; Bartus, R. T.; Powers, J. C. J. Med. Chem. 1993, 36, 3472.
17. Li, Z.; Ortega-Vilain, A.-C.; Patil, G. S.; Chu, D.-L.; Foreman, J. E.; Eveleth, D. D.; Powers, J. C. J. Med. Chem. 1996, 39, 4089.
18. Mehdi, S.; Angelastro, M. R.; Burkhart, J. P.; Kehl, J R.; Peet, N. P.; Bey, P. Biochem. Biophys. Res. Commun. 1990, 166, 595.
19. (a) Street, I. P.; Lin, H.-K.; Laliberte, F.; Ghomashchi, F.; Wang, Z.; Perrier, H.; Tremblay, N. M.; Huang, Z.; Weech, P. K.; Gelb, M. H. Biochemistry 1993, 32, 5935.
20. (b) Ackermann, E. J.; Conde-Frieboes, K.; Dennis, E. A. J. Biol. Chem. 1995, 270, 445.
21. (c) Ghomashchi, F.; Loo, R.; Balsinde, J.; Bartoli, F.; Apitz-Castro, R.; Clark, J. D.; Dennis, E. A.; Gelb, M. H. Biochim. Biophys. Acta 1999, 1420, 45.
22. Simons, J.-W. F. A.; Cox, R. C.; Egmond, M. R.; Verheij H. M. Biochemistry 1999, 38, 6346.
23. Kokotos, G.; Padron, J.-M.; Martin, T.; Gibbons, W. A.; Martin, V. S. J. Org. Chem. 1998, 63, 3741.
24. Kokotos, G.; Noula, C. J. Org. Chem. 1996, 61, 6994.
25. 19F NMR analysis of the corresponding Mosher ester.
26. Sheehan, J. C.; Cruickshank, P. A.; Boshart, G. L. J. Org. Chem. 1961, 26, 2525.
27. Kokotos, G.; Martin, V. S.; Constantinou-Kokotou, V.; Gibbons, W. A. Amino Acids 1996, 11, 329.
28. 3: C, 76.89; H, 12.38; N, 2.42. Found: C, 76.62; H, 12.56; N, 2.34.
29. Verger, R.; de Haas, G. H. Annu. Rev. Biophys. Bioeng. 1976, 5, 77.
30. Ransac, S.; Ivanova, M. G.; Verger, R.; Panaiotov, I. Methods Enzymol. 1997, 286, 263.
31. Verger, R.; de Haas, G. H. Chem. Phys. Lipids 1973, 10, 127.
32. Marguet, F.; Douchet, I.; Cavalier, J.-F.; Buono, G.; Verger, R. Colloids Suif., B 1999, 13, 37.
33. (a) Cavalier, J.-F.; Ransac, S.; Verger, R.; Buono, G. Biochemistry 1995, 34, 2751.
34. (b) Cavalier, J.-F.; Ransac, S.; Verger, R.; Buono, G. Chem. Phys. Lipids 1999, 100, 3.