Heterocyclic ß-keto sulfide derivatives of carvacrol: Synthesis and copper (II) ion reducing capacity.

Cocolas, Alexander H; Parks, Eden L; Ressler, Andrew J; Havasi, Mia H; Seeram, Navindra P; Henry, Geneive E

Cocolas, Alexander H; Parks, Eden L; Ressler, Andrew J; Havasi, Mia H; Seeram, Navindra P; Henry, Geneive E.

Afiliación

Cocolas AH; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
Parks EL; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
Ressler AJ; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA.
Havasi MH; 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.
Henry GE; Department of Chemistry, Susquehanna University, 514 University Avenue, Selinsgrove, PA 17870, USA. Electronic address: henry@susqu.edu.

Bioorg Med Chem Lett ; 29(19): 126636, 2019 10 01.

Article en En | MEDLINE | ID: mdl-31474483

RESUMEN

Sixteen ß-keto sulfide derivatives of carvacrol (4-19) incorporating phenyl or N, O and S heterocyclic moieties were synthesized in three steps. The relationships between heterocyclic structure and cupric, Cu(II), ion reducing antioxidant capacity (CUPRAC) were examined. Nine of the compounds (8-9 and 13-19) showed better CUPRAC activity than trolox at neutral pH, with trolox equivalent antioxidant capacity (TEAC) coefficients ranging between 1.20 and 1.75. Two derivatives (11-12) showed comparable reducing capacity to trolox, with TEAC values of 0.95 for 11 and 1.02 for 12. Compounds 8-9 and 11-19 were more effective at reducing the Cu(II) ion than ascorbic acid and the parent compound, carvacrol. The most effective antioxidants were those containing an oxadiazole, thiadiazole or triazole moiety. In particular, the methyl thiadiazole derivative (15) had the highest Cu(II) ion reducing capacity, with a TEAC coefficient of 1.73.

Asunto(s)

Antioxidantes/síntesis química; Antioxidantes/farmacología; Cobre/química; Cimenos/química; Compuestos Heterocíclicos/química; Sulfuros/química; Cromanos/farmacología; Estructura Molecular

Palabras clave

Antioxidant; Carvacrol; Copper (II) ion reduction; Heterocyclic ß-keto sulfides

Texto completo

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sulfuros / Cobre / Cimenos / Compuestos Heterocíclicos / Antioxidantes 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

Texto completo

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Buscar en Google