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Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol.
Brotzman, Nicholas; Xu, Yiming; Graybill, Allison; Cocolas, Alexander; Ressler, Andrew; Seeram, Navindra P; Ma, Hang; Henry, Geneive E.
Afiliación
  • Brotzman N; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
  • Xu Y; Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA.
  • Graybill A; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
  • Cocolas A; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
  • Ressler A; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
  • Seeram NP; Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA.
  • Ma H; Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA.
  • Henry GE; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA. Electronic address: henry@susqu.edu.
Bioorg Med Chem Lett ; 29(1): 56-58, 2019 01 01.
Article en En | MEDLINE | ID: mdl-30446314
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).
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Timol / Monofenol Monooxigenasa / Monoterpenos / Inhibidores Enzimáticos Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2019 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Timol / Monofenol Monooxigenasa / Monoterpenos / Inhibidores Enzimáticos Idioma: En Revista: Bioorg Med Chem Lett Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2019 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido