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

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
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Aniline, analytical standard
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Sigma-Aldrich
Aniline-15N, 98 atom % 15N
Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Sigma-Aldrich
Aniline, JIS special grade, ≥99.0%
Sigma-Aldrich
Aniline, SAJ first grade, ≥99.0%
Supelco
Aniline solution, certified reference material, 5000 μg/mL in methanol
Sigma-Aldrich
Aniline hydrochloride, ≥99%
Sigma-Aldrich
Kojic acid