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Potent halogenated xanthone derivatives: synthesis, molecular docking and study on antityrosinase activity
Fatin Farhana Baharuddin1, Nadiah Mad Nasir1, Bimo Ario Tejo1
1Department of Chemistry, Universiti Putra Malaysia, UPM Serdang, Selangor 43400, Malaysia.
Abstract:
Tyrosinase inhibitors can reduce melanin production for skin whitening, but some existing products may harm the skin. This study discovered six compounds that inhibit tyrosinase in the mushroom Agaricus bisporus by over 50%. Compound 11 displayed strong inhibition (92.2% and 86.7%) for L-tyrosine and L-DOPA substrates, while compound 13 showed high inhibition (96.0% and 62.0%) for both substrates. Molecular docking simulations revealed compounds 11 and 13 bind at the allosteric site of the enzyme. Xanthone derivatives, based on these findings, hold potential as safe skin whitening agents and for pigmentation-related diseases in the cosmetic industry.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
ortho–para-Directing Deactivators: Halogens