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

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:29

Article

Cocolas, Alexander H.¹  Parks, Eden L.¹  Ressler, Andrew J.¹  Havasi, Mia H.¹  Seeram, Navindra P.²  Henry, Geneive E.¹ 

[1] Susquehanna Univ, Dept Chem, 514 Univ Ave, Selinsgrove, PA 17870 USA

[2] Univ Rhode Isl, Coll Pharm, Dept Biomed & Pharmaceut Sci, Bioact Bot Res Lab, Kingston, RI 02881 USA

关键词: Carvacrol;    Heterocyclic beta-keto sulfides;    Antioxidant;    Copper (II) ion reduction;   

DOI  :  10.1016/j.bmcl.2019.126636

来源: Elsevier

【 摘 要 】

Sixteen beta-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.

【 授权许可】

Free