Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol
Bioorganic & Medicinal Chemistry Letters
Carvacrol (1) and thymol (2) were converted to their alkyl 4-oxobutanoate derivatives (7–20) in three steps, and evaluated for tyrosinase inhibitory activity. The compounds showed structure-dependent activity, with all alkyl 4-oxobutanoates, except 7 and 20, showing better inhibitory activity than the precursor 4-oxobutanoic acids (5 and 6). In general, thymol derivatives exhibited a higher percent inhibitory activity than carvacrol derivatives at 500μM. Derivatives containing three-carbon and four-carbon alkyl groups gave the strongest activity (carvacrol derivatives 9–12, IC50 =128.8–244.1μM; thymol derivatives 16–19, IC50=102.3–191.4μM).
Brotzman, Nicholas, Yiming Xu, Allison Graybill, Alexander Cocolas, Andrew Ressler, Navindra P Seeram, Hang Ma, and Geneive E Henry. “Synthesis and Tyrosinase Inhibitory Activities of 4-Oxobutanoate Derivatives of Carvacrol and Thymol.” Bioorganic & medicinal chemistry letters 29, no. 1 (2019): 56–58.