Department of Chemistry "U. Schiff", University of Florence , Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy.
Department of Chemistry "Ciamician", University of Bologna , Via San Giacomo 11, 40126 Bologna, Italy.
Org Lett. 2016 Nov 4;18(21):5464-5467. doi: 10.1021/acs.orglett.6b02557. Epub 2016 Oct 18.
Noncovalent sulfur···oxygen interactions can increase the stability of chalcogen ortho-substituted phenoxyl radicals. This effect contributes to transforming the 7-hydroxybenzo[b]thiophene moiety in a privileged structural motif to enhance the activity of phenolic antioxidants. A cascade of five consecutive electrophilic reactions occurring in one pot afforded potent and biocompatible α-tocopherol-like antioxidants.
非共价硫···氧相互作用可以提高硫代苯氧自由基邻位取代基的稳定性。这种效应有助于将 7-羟基苯并[b]噻吩部分转化为优势结构基序，以增强酚类抗氧化剂的活性。一锅法中连续发生的五个亲电反应可得到有效且生物相容的 α-生育酚类似物抗氧化剂。
