IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Exploring the Functional Space of Thiiranes as Gelatinase Inhibitors using Click Chemistry
Autor/es:
TESTERO, S.A.; LLARRULL, L.I.; FISHER, J.F.; CHANG, M.; MOBASHERY, S.
Revista:
ARKIVOC - ONLINE JOURNAL OF ORGANIC CHEMISTRY
Editorial:
ARKAT USA INC
Referencias:
Año: 2011 vol. VII p. 221 - 236
ISSN:
1551-7004
Resumen:
A series of 4-[(triazolyl)methoxy]phenyl analogs of the phenoxyphenyl-substituted thiirane SB-3CT 1 was evaluated for its ability to inhibit gelatinases, members of the matrix metalloproteinase family of enzymes. The triazole segment of these inhibitors was assembled using the Meldal-Sharpless copper-catalyzed Huisgen dipolar cycloaddition of an azide and a terminal alkyne. While these triazole derivatives possessed fair activity as gelatinase inhibitors, an intermediate used in the dipolar cycloaddition, 4-(propargyloxy)phenyl derivative 2, showed very good activity (>50% inhibitory activity following a 3 h pre-incubation of 2 at a concentration of 3 ìM) as an inhibitor of human matrix metalloproteinase-2.