Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol
Date of Original Version
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 500 μM. Derivatives containing three-carbon and four-carbon alkyl groups gave the strongest activity (carvacrol derivatives 9–12, IC50 = 128.8–244.1 μM; thymol derivatives 16–19, IC50 = 102.3–191.4 μM).
Publication Title, e.g., Journal
Bioorganic and Medicinal Chemistry Letters
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 and Medicinal Chemistry Letters 29, 1 (2019): 56-58. doi: 10.1016/j.bmcl.2018.11.013.