Design and synthesis of 4-aryl-4-oxobutanoic acid amides as calpain inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 2, 2009, Pages 502-507

  Zhang, Yong ^a,b   Jung, Seo Yoon ^b   Jin, Changbae ^c   Kim, Nam Doo ^d   Gong, Ping ^a   Lee, Yong Sup ^b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b Kyung Hee University   (South Korea)

^c Korea Institute of Science and Technology   (South Korea)

^d Equispharm Co Ltd   (South Korea)

Author keywords

4 Aryl 4 oxobutanoic acid; Calpain inhibitor; Chromone; Ketoamide; Stroke

Indexed keywords

AMIDE; BUTYRIC ACID DERIVATIVE; CALPAIN 1; CALPASTATIN; CHROMONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; IC 50; STRUCTURE ACTIVITY RELATION;

AMIDES; BUTYRIC ACID; CALPAIN; CYSTEINE PROTEINASE INHIBITORS; DRUG DESIGN;

EID: 57749088398     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.030     Document Type: Article

References (15)

1. Suzuki K., Sorimachi H., Yoshizawa T., Kinbara K., and Ishiura S. Biol. Chem. 376 (1995) 523
2. Croall D.E., and DeMartino G.N. Physiol. Rev. 71 (1991) 813
3. Markgraf C.G., Velayo N.L., Johnson M.P., McCarty D.R., Medhi S., Koehl J.R., Chmielwski P.A., and Linnik M. Stroke 29 (1998) 152
4. Boland B., and Campbell V. Neurobiol. Aging 24 (2003) 179
5. Sha D., Jin Y., Wu H., Wei J., Lin C.-H., Lee Y.-H., Buddhala C., Kuchay S., Chishti A.H., and Wu J.-Y. Brain Res. 1207 (2008) 9
6. Kuchay S.M., and Chishti A.H. Curr. Opin. Hematol. 14 (2007) 249
7. Neffe A.T., and Abell A.D. Curr. Opin. Drug Discov. Dev. 8 (2005) 684
8. Mehdi S. Trends Biochem. Sci. 16 (1991) 150
9. Shirasaki Y., Yamaguchi M., and Miyashita H. J. Ocul. Pharmacol. Ther. 22 (2007) 417
10. Lee K.S., Seo S.H., Lee Y.H., Kim H.D., Son M.H., Chung B.Y., Lee J.Y., Jin C., and Lee Y.S. Bioorg. Med. Chem. Lett. 15 (2005) 2857
11. Nam D.H., Lee K.S., Kim S.H., Kim S.M., Jung S.Y., Chung S.H., Kim H.J., Kim N.D., Jin C., and Lee Y.S. Bioorg. Med. Chem. Lett. 18 (2008) 205
12. Lubisch W., Beckenbach E., Bopp S., Hofmann H.-P., Kartal A., Kaestel C., Lindner T., Metz-Garrecht M., Reeb J., Regner F., Vierling M., and Moeller A. J. Med. Chem. 46 (2003) 2404
13. Fieser L.F., Gates M.D., and Kilmer G.W. J. Am. Chem. Soc. 62 (1940) 2966
14. Huffman J.W., Zhang X., Wu M.-J., and Joyner H.H. J. Org. Chem. 56 (1991) 1481
15. 6) δ 199.6, 196.5, 171.5, 160.6, 157.7, 152.8, 152.5, 137.5, 130.8, 129.5 (2C), 129.0 (2C), 128.2 (2C), 127.8, 126.4, 119.3, 114.0, 113.7 (2C), 113.6, 56.2, 55.5, 55.3, 54.9, 40.3, 38.5, 35.1, 33.6, 29.1.