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

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??M. Derivatives containing three-carbon and four-carbon alkyl groups gave the strongest activity (carvacrol derivatives 9-12, IC50?=?128.8-244.1??M; thymol derivatives 16-19, IC50?=?102.3-191.4??M).

SUBMITTER: Brotzman N

PROVIDER: S-EPMC7059125 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Brotzman Nicholas N Xu Yiming Y Graybill Allison A Cocolas Alexander A Ressler Andrew A Seeram Navindra P NP Ma Hang H Henry Geneive E GE

Bioorganic & medicinal chemistry letters 20181108 1

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 ...[more]

PMID: 30446314

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