TY - JOUR
T1 - Tyrosine-like condensed derivatives as tyrosinase inhibitors
AU - Matos, M.J.
AU - Santana, L.
AU - Uriarte, E.
AU - Serra, S.
AU - Corda, M.
AU - Fadda, M.B.
AU - Era, B.
AU - Fais, A.
PY - 2012/5/1
Y1 - 2012/5/1
N2 - Objectives We report the pharmacological evaluation of a new series of 3-aminocoumarins differently substituted with hydroxyl groups, which have been synthesized because they include in their structures the tyrosine fragment (tyrosine-like compounds), with the aim of discovering structural features necessary for tyrosinase inhibitory activity. Methods The synthesized compounds 4 and 7-9 were evaluated in vitro as mushroom tyrosinase inhibitors. Key findings Two of the described compounds showed lower IC50 (concentration giving 50% inhibition of tyrosinase activity) than umbelliferone, used as a reference compound. Conclusions Compound 7 (IC50 = 53 μm) was the best tyrosinase inhibitor of this small series, having an IC50 value 10-fold lower than umbelliferone. Compound 7 (3-amino-7-hydroxycoumarin) had amino and hydroxyl groups precisely mimicking the same positions that both groups occupy on the tyrosine molecule.
AB - Objectives We report the pharmacological evaluation of a new series of 3-aminocoumarins differently substituted with hydroxyl groups, which have been synthesized because they include in their structures the tyrosine fragment (tyrosine-like compounds), with the aim of discovering structural features necessary for tyrosinase inhibitory activity. Methods The synthesized compounds 4 and 7-9 were evaluated in vitro as mushroom tyrosinase inhibitors. Key findings Two of the described compounds showed lower IC50 (concentration giving 50% inhibition of tyrosinase activity) than umbelliferone, used as a reference compound. Conclusions Compound 7 (IC50 = 53 μm) was the best tyrosinase inhibitor of this small series, having an IC50 value 10-fold lower than umbelliferone. Compound 7 (3-amino-7-hydroxycoumarin) had amino and hydroxyl groups precisely mimicking the same positions that both groups occupy on the tyrosine molecule.
UR - http://www.scopus.com/inward/record.url?scp=84859616269&partnerID=8YFLogxK
U2 - 10.1111/j.2042-7158.2012.01467.x
DO - 10.1111/j.2042-7158.2012.01467.x
M3 - Article
AN - SCOPUS:84859616269
SN - 0022-3573
VL - 64
SP - 742
EP - 746
JO - Journal of Pharmacy and Pharmacology
JF - Journal of Pharmacy and Pharmacology
IS - 5
ER -