Solid-phase library synthesis of reversed-statine type inhibitors of the malarial aspartyl proteases plasmepsin I and II

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 6, 2003, Pages 827-841

  Dahlgren, Anders ^a   Kvarnström, Ingemar ^a   Vrang, Lotta ^b   Hamelink, Elizabeth ^b   Hallberg, Anders ^c   Rosenquist, Åsa ^a,b   Samuelsson, Bertil ^b,d  

^a LINKÖPING UNIVERSITY   (Sweden)

^b MEDIVIR AB   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

^d STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 BROMOBENZYLOXY) 3 HYDROXY 4 PENTANOYLAMINO N PHENETHYLBUTYRAMIDE; 4 [(BENZO[1,3]DIOXOL 5 CARBONYL)AMINO] 2 (4 BROMOBENZYLOXY) 3 HYDROXY N (2 PIPERIDIN 1 YLETHYL)BUTYRAMIDE; ANTIMALARIAL AGENT; ASPARTIC PROTEINASE INHIBITOR; PLASMEPSIN I; PLASMEPSIN II; PROTOZOAL PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; IC 50; PLASMODIUM FALCIPARUM; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

AMINO ACIDS; ANIMALS; ANTIMALARIALS; ASPARTIC ENDOPEPTIDASES; CROSS-LINKING REAGENTS; ENZYME INHIBITORS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE LIBRARY; PLASMODIUM; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM FALCIPARUM;

EID: 0037333352     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00568-0     Document Type: Article

References (39)

1. Radding J.A. Annu. Rep. Med. Chem. 34:1999;159.
2. Oaks S.C. Jr., Mitchell V.S., Pearson G.W., Carpenter C.C.J. Malaria: Obstacles and Opportunities: A Report of the Committee for the Study on Malaria Prevention and Control: Status Review and Alternative Strategies, Division of International Health, Institute of Medicine. 1991;National Academy, Washington, DC.
3. Francis S.E., Sullivan D.J., Goldberg D.E. Annu. Rev. Microbiol. 51:1997;97.
4. Scheibel, L. W.; Sherman, I. W. In Malaria, Wernsdofer, W. H.; McGregor, I., Eds.; Churchill Livingstone: London, 1988; p. 219.
5. Slater A.F.G. Pharmacol. Ther. 57:1993;203.
6. Wirth D.F. Annu. Rep. Med. Chem. 34:1999;349.
7. (a) Francis, S. E.; Gluzman, I. Y.; Oksman, A.; Knickerbocker, A.; Mueller, R.; Bryant, M.; Sherman, D. R.; Russell, D. G.; Goldberg, D. E. Embo. J. 1994, 93, 306.
8. (b) Gluzman, I. Y.; Francis, S. E.; Oksman, A.; Smith, C. E.; Duffin, K. L.; Goldberg, D. E. J. Clin. Invest. 1994, 93, 1602.
9. (c) Dame, J. B.; Reddy, G. R.; Yowell, C. A.; Dunn, B. M.; Kay, J.; Berry, C. Mol. Biochem. Parasitol. 1994, 64, 177.
10. (a) Rosenthal, P. J.; Olson, J. E.; Lee, K.; Palmer, J. T. Antimicrob. Agents Chemother. 1996, 40, 1600.
11. (b) Rosenthal, P. J. Exp. Parasitol. 1995, 80, 272.
12. (c) Rosenthal, P. J.; McKerow, J. H.; Rasnick D.; Leech, J. H. Mol. Biochem. Parasitol. 1989, 35, 177.
13. (d) Rosenthal, P. J.; Wollish, W. S.; Palmer, J. T., Rasnick D. J. Clin. Invest. 1991, 88, 1467
14. Coombs G.H., Goldberg D.E., Klemba M., Berry C., Kay J., Mottram J.C. Trends Parasitol. 17:2001;532.
15. See, for example: Haque T.S., Skillman A.G., Lee C.E., Habashita H., Gluzman I.Y., Ewing T.J.A., Goldberg D.E., Kuntz I.D., Ellman J.A. J. Med. Chem. 42:1999;1428.
16. Silva A.M., Lee A.Y., Gulnik S.V., Majer P., Collins J., Bhat T.N., Collins P.J., Cachau R.E., Luker K.E., Gluzman I.Y., Francis S.E., Oksman A., Goldberg D.E., Erickson J.W. Proc. Natl. Acad. Sci. U.S.A. 93:1996;10034.
17. See, for example: Abushanab E., Vemishetti P., Leiby R.W., Singh H.K., Mikkilineni A.B., Wu D. C-J., Saibaba, R., Panzica, R. P. J. Org. Chem. 53:1988;2598. and references therein.
18. Wei C.C., De Bernardo S., Tengi J.P., Borgese J., Weigele M. J. Org. Chem. 50:1985;3462.
19. See, for example: Mayer P., Ahond A., Poupat C., Potier P. Bull. Soc. Chim. Fr. 130:1993;509.
20. See, for example: Joachimi D., Öhlmann A., Rettig W., Tschierske C. J. Chem. Soc., Perkin. Trans. 2. 9:1994;2011.
21. 2O proved to benefit the yields of the reactions.
22. The benzylations with m-bromobenzyl bromide required higher temperatures and longer reaction times compared to the benzylations where p-bromobenzyl bromide was used.
23. Some lactonization could be observed during the course of these reactions.
24. In the azide displacement step the m-bromo compounds required slightly longer reaction times than the corresponding p-bromo compounds.
25. Thompson L.A., Ellman J.A. Tetrahedron Lett. 35:1994;9333.
26. Bunin, A. B. In The Combinatorial Index, Academic Press: San Diego, 1998; p. 219.
27. Chen, Y. Unpublished results. For additional information, contact: Dr. Yantao Chen, Department of Chemistry, Linköping University, S-581 83 Linköping, Sweden.
28. In most cases, the crude products after cleavage from the resin were contaminated only with a small amount of polar baseline (according to TLC) material.
29. Alterman M., Björsne M., Mühlman A., Classon B., Kvarnström I., Danielson H., Markgren P.O., Nillroth U., Unge T., Hallberg A., Samuelsson B. J. Med. Chem. 41:1998;3782.
30. Lee C.E., Kick E.K., Ellman J.A. J. Am. Chem. Soc. 120:1998;9735.
31. Bartra M., Romea P.L., Urpí F., Vilarrasa J.A. Tetrahedron. 46:1990;587.
32. We observed that ester formation was a notable side reaction in these coupling reactions when indanolamine was a part of the resin bound molecules.
33. Ward P., Armour D.R., Bays D.E., Evans B., Giblin G.M.P., Heron N., Hubbard T., Liang K., Middlemiss D., Mordaunt J., Naylor A., Pegg N.A., Vinader M.V., Watson S.P., Bountra C., Evans D.C. J. Med. Chem. 38:1995;4985.
34. Bold G., Fässler A., Capraro H.G., Cozens R., Klimkait T., Lazdins J., Mestan J., Poncioni B., Rösel J., Stover D., Tintelnot-Blomley M., Acemoglu F., Ucci-Stoll K., Wyss D., Lang M. J. Med. Chem. 41:1998;3387.
35. (a) Lipinski, C.,A.; Lombardo, F.; Dominy, B.,W.; Feeney, P.,J. Adv. Drug Deliv. Rev. 1997, 23, 3.
36. (b) Lipinski, C. A. In Tools for Oral Absorption. Part Two. Predicting Human Absorption; BIOTEC, PDD Symposium, AAPS, Miami, 1995.
37. Manuscript in preparation.
38. Copeland, R. A., Ed. Enzymes: A Practical Introduction to Structure, Mechanism, and Data Analysis, 2nd ed.; John Wiley & Sons: New York, 2000.
39. Cheng Y., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099.