ChemInform Abstract: Synthesis of 5-(1-Substituted Ethyl)uracil Derivatives and Some of Their Chemical and Biological Properties.
Abstract
Reaction of the deoxyuridine (I) with thiophenol (II) under radical conditions gives the 2-phenylthioethyl deoxyuridine (IIIa), which can be oxidized to the sulfone (IIIb) (MCPBA, 42% yield) or the sulfoxide (IIIc) (NaIO4, 91%).
ChemInform Abstract
Reaction of the deoxyuridine (I) with thiophenol (II) under radical conditions gives the 2-phenylthioethyl deoxyuridine (IIIa), which can be oxidized to the sulfone (IIIb) (MCPBA, 42% yield) or the sulfoxide (IIIc) (NaIO4, 91%). In the presence of the radical inhibitor BHS, (I) reacts with the thiols (IV) to give the 1-arylthioethyl deoxyuridines (V), part of which undergo oxidation to the sulfones (VIa) or the sulfoxides (VIb). The compounds (V) and (VI) are investigated as possible precursors of (I) by studying their reactions under basic conditions. Compounds (III), (V) and (VI) are evaluated for antiviral and antitumor-cell activities.
