Amino acid derived latent isocyanates: irreversible inactivation of porcine pancreatic elastase and human leukocyte elastase

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Abstract
Several amino acid derived azolides were synthesized and investigated for their inhibitory activity toward human leukocyte elastase and porcine pancreatic elastase. The inhibitory activity was dependent on the nature of the precursor amino acid ester. Compounds derived from L-valine methyl ester, L-norvaline methyl ester, DL-norleucine methyl ester, and L-methionine methyl ester 10 inhibited irreversibly both enzymes. Compound 10 was a specific and selective inhibitor of human leukocyte elastase. Inhibitors derived from glycine methyl ester, D-valine methyl ester, and D-norvaline methyl ester were inactive. Latent isocyanates derived from appropriate amino acids can evidently serve as selective inhibitors of serine proteases and are of potential pharmacological value in pulmonary emphysemea.