Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

Authors

Nicholas Brotzman, Susquehanna University
Yiming Xu, University of Rhode Island
Allison Graybill, Susquehanna University
Alexander Cocolas, Susquehanna University
Andrew Ressler, Susquehanna University
Navindra P. Seeram, University of Rhode Island
Hang Ma, University of Rhode Island
Geneive E. Henry, Susquehanna University

Document Type

Article

Date of Original Version

1-1-2019

Abstract

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

Volume

29

Issue

1

Citation/Publisher Attribution

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.