953792-02-4

Upstream product

• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 260366-28-7 2',3'-dideoxy-3'-(2-(trimethylsilyl)ethyl)thiothymidine 

Relevant academic research and scientific papers

Anti-retroviral and cytostatic activity of 2′,3′-dideoxyribonucleoside 3′-disulfides

Herein, we report the synthesis, antiviral and cytostatic effects of nucleosides bearing a 3′-disulfide function as prodrugs of potentially active 3′-mercaptonucleotides. The lack of the anti-HIV effects in mutant CEM/TK-cells for most of the thymidine disulfides suggests that a phosphorylation step involving thymidine kinase is necessary for the eventual antiviral activity of the thymidine nucleosides. The comparable anti-HIV activities of most of the disulfides and their rapid reduction in CEM cell extracts imply an inhibitory effect of the 2′,3′-dideoxy-3′-mercaptothymidine 5′-triphosphate metabolite. The cytostatic effects of the disulfides in CEM/0 and Molt4/C8 cells appeared to be strongly dependent on the nature of the non-nucleosidic disulfide moiety and were decreased in preserving the anti-retroviral activity.

PROCESS FOR PREPARING DISULPHIDES AND THIOSULPHINATES AND COMPOUNDS PREPARED

Process for preparing a compound of the formula (I) R1-S(O)x—S(O)yR2 in which R1 represents a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen; R2, independently of R1, represents a carbon-containing group or a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen, and x and y are selected from 0 and 1 in such a way that the sum of x and y is not more than 1, characterized in that a compound of formula (II) R1-S(O)x—R3-Si(R4)(R5)(R6) in which R3 represents a hydrocarbon chain of two carbon atoms, which is optionally unsaturated and/or substituted, and R4, R5 and R6, which are identical or different, each represent, independently of one another, a hydrocarbon group, is reacted with a compound of formula (VII) R2-S(O)y—X in which X represents a halogen, intermediate compounds, and compounds prepared.