Synthesis and anti-elastase properties of 6-amino-2-phenyl-4H-3,1-benzoxazin-4-one aminoacyl and dipeptidyl derivatives

A series of 6-amino-2-phenyl-4H-3,1-benzoxazin-4-one aminoacyl and dipeptidyl derivatives, in which aminoacids and dipeptides are linked to the benzoxazinone moiety via an amide bond, were synthesized and tested in vitro for their inhibitory activity towards human leukocyte elastase (HLE). When comp...

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Bibliographic Details
Published in:Biochimie 2005-02, Vol.87 (2), p.223-230
Main Authors: Colson, Eric, Wallach, Jean, Hauteville, Marcelle
Format: Article
Language:English
Subjects:
Benzoxazoles - chemical synthesis
Benzoxazoles - chemistry
Dipeptides - chemical synthesis
Dipeptides - chemistry
Enzyme Activation - drug effects
Humans
Leukocyte Elastase - antagonists & inhibitors
Serine Proteinase Inhibitors - chemical synthesis
Serine Proteinase Inhibitors - chemistry
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Summary:A series of 6-amino-2-phenyl-4H-3,1-benzoxazin-4-one aminoacyl and dipeptidyl derivatives, in which aminoacids and dipeptides are linked to the benzoxazinone moiety via an amide bond, were synthesized and tested in vitro for their inhibitory activity towards human leukocyte elastase (HLE). When compared to their values without inhibitors, the residual enzymatic activities decrease with time, indicating a time-dependent inhibition. The most potent inhibitions were obtained when Z-Arg-(Pmc), Z-Val-Phe, Z-Ala-Val or Z-Val-Ala are linked to the 6-amino group. Twenty-five new compounds were synthesized.
ISSN:0300-9084
DOI:10.1016/j.biochi.2004.10.015