Photochemistry of Di(deoxyribonucleoside) Methylphosphonates Containing N3-Methyl-4-thiothymine

Synthesis and Antiviral Activity of 1,3-Disubstituted Uracils against HIV-1 and HCMV

“…Methods for thiation of uracil or uridine have been universally reported. Recently, 3-alkyluracils was converted to the 4-thio congener by Lawesson's reagent (Clivio et al, 1992;Clivio et al, 1994). We adopted this method for the synthesis of compounds 8a-c ( Figure 2).…”

Synthesis of the TT pyrimidine (6–4) pyrimidone photoproduct–thio analogue phosphoramidite building block

“…14 We also reasoned that the P-methoxy group was structurally close to the P-methyl group that was previously found not to interfere with the photochemical pathway leading to (6-4) PPs. 15 The synthetic route envisaged to obtain 2, compared to the corresponding method in the natural series, had to solve a major difficulty inherent to the presence of the sulfur atom. Thus, with regards to phosphoramidite chemistry, 4-thiothymine had to be incorporated either under a protected form (Spivaloyloxymethyl or S-cyanoethyl) 16 for the formation of the internucleotide phosphotriester linkage or generated by thiol displacement of a pyrimidine activated at the 4-position 12,17 after the formation of the internucleotide phosphotriester linkage.…”

Synthesis and properties of (6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)acetic acid methyl ester

“…IR spectrum, ν, cm -1 : 1678, 1698 (C=O); 3078, 3203 (NH). 1 H NMR spectrum, δ, ppm: 1.89 (3H, s, (11). Ethyl-or phenylhydrazine (8 mmol) was added to a solution of compound 2 (0.43 g, 2 mmol) in absolute methanol (2 ml).…”

“…The reaction mixture was boiled in an argon atmosphere for 13 h, and cooled to room temperature. The precipitated solid was filtered off, washed with methanol, and recrystallized from a DMF-water mixture (for compound 10) or 2-propanol (11). …”