Palomino, Eduardo; Meltsner, Bernard R.; Kessel, David; Horwitz, Jerome P. published an article on January 31 ,1990. The article was titled 《Synthesis and in vitro evaluation of some modified 4-thiopyrimidine nucleosides for prevention or reversal of AIDS – associated neurological disorders》, and you may find the article in Journal of Medicinal Chemistry.Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate The information in the text is summarized as follows:
Oxygen-sulfur exchange at the C-4 carbonyl of several modified pyrimidine nucleosides, including 3′-azido-3′-deoxythymidine (AZT), is described in an effort to enhance the lipophilicity and, thereby, the delivery to the central nervous system of the sulfur analogs without compromising the anti-HIV activities of the parental structures. Preparation of 3′-azido-3′-deoxy-4-thiothymidine (I) proceeded from 4-thiothymidine and utilized the same methodol. developed for the initial synthesis of AZT. Thiation of 2′,3′-didehydro-3′-deoxythymidine and 2′,3′-didehydro-2′,3′-dideoxyuridine was carried out with Lawesson’s reagent on the corresponding 5′-O-benzoate esters. The products on alk. hydrolysis gave 2′,3′-didehydro-3′-deoxy-4-thiothymidine and 2′,3′-didehydro-2′,3′-dideoxy-4-uridine (III). The same series of reactions were applied to the 5′-O-benzoate esters of 2′,3′-dideoxyuridine and 3′-deoxythymidine to give 2′,3′-dideoxy-4-thiouridine (IV) and 3′-deoxy-4-thiothymidine (V). Characterization of the saturated and unsaturated thionucleosides included mass spectrometric studies. Under electron impact conditions, the thiated analogs gave more intense parent ions than the corresponding oxygen precursors. The lipophilicity of thymidine and the 3′-deoxythymidine derivatives are enhanced significantly, as indicated, by increases in corresponding P values (1-octanol-0.1M sodium phosphate) upon replacement of the 4-carbonyl oxygens by sulfur. II, III, IV, and V were evaluated for their effects on HIV-induced cytopathogenicity of MT-2 and CEM cells. Only II and V were moderately active in protecting both cell lines against the cytolytic effect of HIV. The inhibitory effects of II-V on thymidine phosphorylation by rabbit thymus thymidine kinase were evaluated. Only I showed moderate affinity (Ki = 54 μM) for the enzyme. The generally weak anti-HIV activities of the remaining thio analogs are consistent with correspondingly low susceptibilities to thymidine kinase phosphorylation as estimated from the resp. Ki values of the synthetic nucleosides. However, the phosphorylation of the 5′-monophosphate derivatives to their resp. 5′-triphosphates must also be considered in connection with the weak in vitro anti-HIV effects of these thiated compounds The experimental process involved the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate)
((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Application In Synthesis of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia