Synthesis of Fluorinated N- Benzylaniline Derivatives and Evaluations on Anti-Tyrosinase and Anti-Melanogenic Activities

Autor: Kanokwan Singpanna, Panupun Limpachayaporn, Monrudee Sukma, Anan Athipornchai, Nopparat Nuntharatanapong
Rok vydání: 2022
Předmět:
Zdroj: Key Engineering Materials. 914:87-92
ISSN: 1662-9795
Popis: Melasma, freckles, age spots, and acne scars are common aesthetic problems resulted from melanin overproduction. This study aimed to develop new skin depigmenting compounds and characterize on melanin inhibition activities. The fluorinated N-benzylaniline derivatives were synthesized and evaluated for their in vitro anti-tyrosinase activity. Derivatives with p-fluorine monosubstition, N-(4-fluorobenzyl)-3-fluoro-4-methoxyaniline (3d), was the most potent inhibitor against mushroom tyrosinase with 75.4 ± 0.34 % inhibition at 500 µM which was as potent as the positive control, kojic acid. Furthermore, compound 3d exhibited superior anti-melanogenic activity in α-MSH-induced B16F10 murine melanoma cells, compared to kojic acid. Therefore, N-(4-fluorobenzyl)-3-fluoro-4-methoxyaniline (3d) was proposed as a new agent effective against skin hyperpigmentation.
Databáze: OpenAIRE