3-Amino-2-hydroxy-propionaldehyde and 3-amino-1-hydroxypropan-2-one derivatives: New classes of aminopeptidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 8, 1996, Pages 1287-1297

  Tarnus, Céline ^a   Rémy, Jean Marc ^a   D'Orchymont, Hugues ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BESTATIN; CYTOSOL AMINOPEPTIDASE; ENZYME INHIBITOR; LEUCINAL; MICROSOMAL AMINOPEPTIDASE; PROPANOLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; STRUCTURE ACTIVITY RELATION;

EID: 0030221404     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00115-0     Document Type: Article

References (45)

1. 1. Taylor, A. FASEB J. 1993, 290.
2. 2. Sanderink, G.-J.; Artur, Y.; Siest, G. J. Clin. Chem. Clin. Biochem. 1988, 26, 795.
3. 3. McDonald, J. K.; Schwabe, E. C. Proteinases in Mammalian Cells and Tissues; Elsevier/North Holland: Amsterdam, 1977; pp 311-392.
4. 4. Giros, B.; Gros, C.; Solhonne, B.; Schwartz, J. C. Mol. Pharmacol. 1986, 29, 281.
5. 5. Ward, P. E.; Benter, I. F.; Dick, L.; Wilk, S. Biochem. Pharmacol. 1990, 40, 1725.
6. 6. Powers, J. C.; Harper, J. W. In Proteinases Inhibitors Barrett, A. J.; Salvesen, G. Eds; Elsevier, Amsterdam, 1986; pp 219-298.
7. 7. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H. J. Med. Chem. 1977, 20, 510.
8. 8. Tobe, H.; Morishima, H.; Aoyagi, T.; Umezawa, H.; Ishiki, K.; Nakamura, K.; Yoshioka, T.; Schimauchi, Y.; Inui, T. Agric. Biol. Chem. 1982, 46, 1865.
9. 9. Umezawa, H. In Small Molecular Immunomodifiers of Microbial Origin, Fundamental and Clinical Studies of Bestatin; Umezawa, H., Ed.; Japan Scientific Societies and Pergamon: Oxford, 1981.
10. 10. Kim, H.; Lipscomb, W. N. Biochemistry 1993, 32, 8465.
11. 11. Frick, L.; Wolfenden, R. Biochem. Biophys. Acta 1985, 529, 311.
12. 12. Andersson, L.; MacNeela, J.; Wolfelden, R. Biochemistry 1985, 24, 330.
13. 13. Andersson, L.; Isley, T. C.; Wolfenden, R. Biochemistry 1982, 21, 4177.
14. 14. Wohl, A.; Schweitzer, H. Chem. Ber. 1907, 40, 92.
15. 15. Fischer, H. O. L.; Baer, E.; Nidecker, H. Helv. Chim. Acta 1935, 18, 1079.
16. 16. Jackson, A. O.; Marvel, C. S. J. Biol. Chem. 1933, 103, 191.
17. 17. Waszkuc, W.; Janecki, T.; Bodalski, R. Synthesis 1984, 1025.
18. 18. Kirmann, A.; Druesne, F. C. R. Acad. Sc. Paris 1964, 259, 3285.
19. 19. Lobry De Bruyn, C. A.; Aberda van Ehenstein, W. Chem. Ber. 1895, 28, 3078.
20. 20. Kornblum, N.; Larson, H. O.; Blackwood, R. K.; Mooberry, D. D.; Oliveto, E. P.; Graham, G. E. J. Am. Chem. Soc. 1956, 78, 1497.
21. 21. Varma, R. S.; Kabalka, G. W. Synth. Commun. 1985, 15, 151.
22. 22. Gairaud, C. B.; Lappin, G. R. J. Org. Chem. 1953, 18, 1.
23. 23. Sangsari, F. H.; Chastrette, F.; Chastrette, M. Synth. Commun. 1988, 18, 1343.
24. 24. Stassinopoulou, C. I.; Zioudrou, C. Tetrahedron 1972, 28, 1257.
25. 25. Kirrmann, A.; Cantacuzène, J.; Vio, L.; Martin, M. Bull. Soc. Chim. France 1963, 1067.
26. 26. Aminoacetaldehyde, diethyl acetal was produced as a side-product during the reduction of 2b by hydrazine over Raney nickel. Subsequently, BOC-aminoacetaldehyde diethyl acetal was treated with 37% HCl 5 min under reflux to give aminoacetaldehyde hydrochloride.
27. 27. Creary, X.; Rollin, A. J. J. Org. Chem. 1977, 42, 4231.
28. 4Cl displays two pseudo triplets at δ 7.30 and 7.32 with a 51 Hz line separation at 360 MHz.
29. 29. d'Orchymont, H.; Tarnus, C. US Patent 1992, 5, 106,861.
30. 30. Tinapp, P. Chem. Ber. 1971, 104, 2266.
31. 31. For 5b and 5c, a single pair of enantiomers was tested. It is likely that epimerization of the chiral carbon χ. to the hydroxyl group occurs rapidly at the test conditions at pH 7-8.
32. 32. For example, the presence of water bound to the catalytic zincs was revealed in the structure of native Aeromonas proteolytica aminopeptidase. Chevrier, B.; Schalk, C.; d'Orchymont, H.; Rondeau, J.-M.; Moras, D.; Tarnus, C. Structure 1994, 2, 283.
33. 33. Fittkau, S.; Jahreis, G.; Peters, K.; Bulaspiri, L. J. Prakt. Chem. 1986, 328, 529.
34. 34. Wilkes, S. H.; Prescott, J. M. J. Biol. Chem. 1983, 258, 13517.
35. 35. Chan, W. W.-C.; Dennis, P.; Demmer, W.; Brand, K. J. Biol. Chem. 1982, 257, 7955.
36. 36. Holmes, M. A.; Matthews, B. W. Biochemistry 1981, 20, 6912.
37. 37. Borkakoti, N.; Winkler, F. K.; Williams, D. H.; D'Arcy, A.; Broadhurst, M. J.; Brown, P. A.; Johnson, W. H.; Murray, E. J. Nature Struc. Biol. 1994, 1, 106.
38. 38. Stams, T.; Spurlino, J. C.; Smith, D. L.; Wahl, R. C; Ho, T. F.; Qoronfleh, M. W.; Banks, T. M.; Rubin, B. Nature Struc. Biol. 1994, 1, 119.
39. 39. Wacker, H.; Lehky, P.; Fischer, E. H.; Stein, E. A. Helv. Chim. Acta 1971, 54, 473.
40. 40. Söderling, E. Prep. Biochem. 1980, 10, 191.
41. 41. Schalk, C.; Remy, J.-M.; Chevrier, B.; Moras, D.; Tarnus, C. Arch. Biochem. Biophys. 1992, 294, 91.
42. 42. Schalk, C.; d'Orchymont, H.; Jauch, M. F.; Tarnus, C. Arch. Biochem. Biophys. 1994, 311, 42.
43. 43. Tuppy, H.; Wiesbauer, W.; Wintersberger, E. Hoppe-Seyler's Z. Physiol. Chem. 1962, 329, 278.
44. 44. Segel, I. H. Enzyme Kinetics; John Wiley & Sons, New York, 1975.
45. 45. Wilkes, S. H.; Prescott, J. M. J. Biol. Chem. 1985, 260, 13154.