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 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.
Colson
Eric
E
Laboratoire de Biochimie Analytique et Synthèse Bioorganique, Université Claude Bernard Lyon 1, 43, boulevard du 11 Novembre 1918, 69 622 Villeurbanne cedex, France.
Wallach
Jean
J
Hauteville
Marcelle
M
D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004789:Enzyme Activation / Q000187:drug effects; D006801:Humans; D019272:Leukocyte Elastase / Q000037:antagonists & inhibitors*; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry
D001583:Benzoxazoles; D004151:Dipeptides; D015842:Serine Proteinase Inhibitors; D019272:Leukocyte Elastase