Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 4, 1998, Pages 333-338

  Adams, Julian ^a   Behnke, Mark ^a   Chen, Shaowu ^a   Cruickshank, Amy A ^a   Dick, Lawrence R ^a   Grenier, Louis ^a   Klunder, Janice M ^a   Ma, Yu Ting ^a   Plamondon, Louis ^a   Stein, Ross L ^a  

^a ProScript Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; PROTEASOME; PROTEINASE INHIBITOR;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; CONTROLLED STUDY; ENZYME ACTIVITY; IN VITRO STUDY; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN DEGRADATION;

BORONIC ACIDS; CYSTEINE ENDOPEPTIDASES; MOLECULAR STRUCTURE; MULTIENZYME COMPLEXES; PROTEASE INHIBITORS; PROTEASOME ENDOPEPTIDASE COMPLEX;

EID: 0032539702     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00029-8     Document Type: Article

References (25)

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9. 6. Inhibition of the chymotryptic-like proteolytic activity of rabbit muscle 20S proteasome. Proteasome isolation, purification, and assays were performed as previously described. Stein, R. L.; Melandri, F.; Dick, L. Biochemistry 1996, 35, 3899.
10. 7. Compound 8 was prepared by coupling L-Leu-chloromethylketone hydrochloride with Cbz-L-Leu-L-Leu-OH (isobutyl chloroformate, N-methylmorpholine, THF). Compounds 9-11 were prepared according to standard literature procedures. Trifluoromethylketones: Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760. Ketobenzoxazoles: Edwards, P. D.; Meyer, E. F., Jr.; Vijayalakshmi, J.; Tuthill, P. A.; Andisik, D. A.; Gomes, B.; Strimpler, A. J. Am. Chem. Soc. 1992, 114, 1854. Diketoesters: Wasserman, H. H.; Ennis, D. S.; Blum, C. A.; Rotello, V. M. Tetrahedron Lett. 1992, 33, 6003; Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 5205.
11. 7. Compound 8 was prepared by coupling L-Leu-chloromethylketone hydrochloride with Cbz-L-Leu-L-Leu-OH (isobutyl chloroformate, N-methylmorpholine, THF). Compounds 9-11 were prepared according to standard literature procedures. Trifluoromethylketones: Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760. Ketobenzoxazoles: Edwards, P. D.; Meyer, E. F., Jr.; Vijayalakshmi, J.; Tuthill, P. A.; Andisik, D. A.; Gomes, B.; Strimpler, A. J. Am. Chem. Soc. 1992, 114, 1854. Diketoesters: Wasserman, H. H.; Ennis, D. S.; Blum, C. A.; Rotello, V. M. Tetrahedron Lett. 1992, 33, 6003; Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 5205.
12. 7. Compound 8 was prepared by coupling L-Leu-chloromethylketone hydrochloride with Cbz-L-Leu-L-Leu-OH (isobutyl chloroformate, N-methylmorpholine, THF). Compounds 9-11 were prepared according to standard literature procedures. Trifluoromethylketones: Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760. Ketobenzoxazoles: Edwards, P. D.; Meyer, E. F., Jr.; Vijayalakshmi, J.; Tuthill, P. A.; Andisik, D. A.; Gomes, B.; Strimpler, A. J. Am. Chem. Soc. 1992, 114, 1854. Diketoesters: Wasserman, H. H.; Ennis, D. S.; Blum, C. A.; Rotello, V. M. Tetrahedron Lett. 1992, 33, 6003; Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1990, 31, 5205.
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25. 18. Preliminary information about compound 15 and its proteasome inhibitory activity has been disclosed previously. See reference 2.