Hydroxyoxazolidines as alpha-aminoacetaldehye equivalents: novel inhibitors of calpain

N P Peet; H O Kim; A L Marquart; M R Angelastro; T R Nieduzak; J N White; D Friedrich; G A Flynn; M E Webster; R J Vaz; M D Linnik; J R Koehl; S Mehdi; P Bey; B Emary; K K Hwang

doi:10.1016/s0960-894x(99)00391-1

Hydroxyoxazolidines as alpha-aminoacetaldehye equivalents: novel inhibitors of calpain

Bioorg Med Chem Lett. 1999 Aug 16;9(16):2365-70. doi: 10.1016/s0960-894x(99)00391-1.

Authors

N P Peet¹, H O Kim, A L Marquart, M R Angelastro, T R Nieduzak, J N White, D Friedrich, G A Flynn, M E Webster, R J Vaz, M D Linnik, J R Koehl, S Mehdi, P Bey, B Emary, K K Hwang

Affiliation

¹ Hoechst Marion Roussel, Inc., Bridgewater, NJ 08807, USA.

PMID: 10476870
DOI: 10.1016/s0960-894x(99)00391-1

Abstract

The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropy lcarbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2.

MeSH terms

Calpain / antagonists & inhibitors*
Carbamates / chemistry
Carbamates / pharmacology*
Magnetic Resonance Spectroscopy
Oxazoles / chemistry
Oxazoles / pharmacology*
Protease Inhibitors / chemistry
Protease Inhibitors / pharmacology*

Substances

Carbamates
MDL 104903
Oxazoles
Protease Inhibitors
Calpain