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Design, synthesis, and evaluation of (E)-N-substituted benzylidene-aniline derivatives as tyrosinase inhibitors.

European journal of medicinal chemistry (2012-11-15)
Sung Jin Bae, Young Mi Ha, Yun Jung Park, Ji Young Park, Yu Min Song, Tae Kwun Ha, Pusoon Chun, Hyung Ryong Moon, Hae Young Chung
RÉSUMÉ

We attempted to design and synthesize (E)-N-substituted benzylidene-hydroxy or methoxy-aniline derivatives and to evaluate their inhibitory effect on tyrosinase activity and anti-melanogenesis activity in murine B16F10 melanoma cells. Derivatives with a 4-methoxy- or 4-hydroxy-anilino group exerted more potent inhibition against mushroom tyrosinase than those with a 2-hydroxyanilino group. (E)-4-((4-Hydroxyphenylimino)methyl)benzene-1,2-diol exhibited the most potent and non-competitive inhibition on mushroom tyrosinase showing an IC(50) of 17.22 ± 0.38 μM and being more effective than kojic acid (51.11 ± 1.42 μM). This compound decreased melanin production stimulated by the alpha-melanocyte-stimulating hormone and inhibited murine tyrosinase activity in a dose-dependent manner. Therefore, we propose (E)-4-((4-hydroxyphenylimino)methyl)benzene-1,2-diol as a new candidate of potent tyrosinase inhibitors that could be used as therapeutic agent with safe skin-whitening efficiency.

MATÉRIAUX
Référence du produit
Marque
Description du produit

Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Sigma-Aldrich
Kojic acid
Sigma-Aldrich
Aniline hydrochloride, ≥99%
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Supelco
Aniline, analytical standard
Sigma-Aldrich
Aniline-15N, 98 atom % 15N
Supelco
Aniline solution, certified reference material, 5000 μg/mL in methanol