Synthesis of Avicequinone C and Analogs Toward the Study of 5α-Reductase Inhibitory Activity

    January 2015
    Wiranpat Karnsomwan
    TLDR 2-Hydroxy-1,4-naphthoquinone is a strong 5α-reductase inhibitor.
    The study focused on synthesizing avicequinone C and its analogs to investigate their 5α-reductase (5α-R) inhibitory activity, an enzyme involved in conditions like androgenic alopecia. Using in silico modeling and molecular docking simulations, avicequinone C showed promising binding interactions at the 5α-R catalytic site. However, in vitro assays using the HaCaT cell line revealed that 2-hydroxy-1,4-naphthoquinone was a more potent inhibitor, with 82.73% inhibition at 40 µM and an IC50 of 23.93 µM, surpassing avicequinone C. The study concluded that the naphthoquinone structure is crucial for 5α-R inhibition, and the developed 3D model of 5α-R1 could aid future inhibitor development.
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