Synthesis and Evaluation of Antiviral Activity of 2'-Deoxyuridines with 5-Methylene-2-thiohydantoin Substituents in the 5-Position

Article abstract of DOI:10.1007/BF00811853

1-(2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)-5-formyluracil (4) was synthesized from 5-formyluracil and an appropriate methyl glycoside and condensed with 2-thiohydantoin (5a) and its corresponding 3-phenyl derivative 5b to give 5-<1-(2-deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl)uracil-5-ylmethylene>-2-thiohydantoins 7a and 7b, respectively, in 65-70percent yield.They were deprotected with sodium methoxide in methanol to give both anomers of the free nucleosides.In a different route 5-formyluracil (1) was condensed with 5b and subsequently with an appropriate methyl glycoside to give 7b. - Keywords: 2'-Deoxyuridines; 2-Thiohydantoins; Nucleoside synthesis; Antiviral activity.