6741-73-7

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-thio-beta-D-ribofuranosyl)uracil is used as an anti-viral and anti-cancer agent for its potential therapeutic effects against viral infections and cancer cells.
Used in Research and Development:
1-(4-thio-beta-D-ribofuranosyl)uracil is used as a research tool for investigating the effects of thiol modifications on RNA stability and function, contributing to a better understanding of RNA biology and its role in diseases.
Used in Genetic Research:
1-(4-thio-beta-D-ribofuranosyl)uracil is used as a mutagen in experimental studies to induce genetic mutations and analyze their consequences on cellular processes and phenotypes.

Upstream product

• 66-22-8 uracil 
• 875753-50-7 tert-butyl-(2,2-dimethyl-5-oxo-tetrahydro-5λ⁴-thieno[3,4-d][1,3]dioxol-4-ylmethoxy)-dimethyl-silane 
• 875753-49-4 tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)dimethylsilane 
• 596103-06-9 ((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol 
• 875753-48-3 (3aR,6S,7R,7aR)-6-Methoxy-2,2-dimethyl-tetrahydro-thiopyrano[3,4-d][1,3]dioxol-7-ol 
• 218906-61-7 methyl 5-thio-β-L-arabinopyranoside 
• 291758-14-0 1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-d-ribofuranosyl] uracil 
• 291758-14-0 1-[2-O-(2,4-dimethoxybenzoyl)-2,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]uracil 
• 291758-26-4 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose 
• 869347-03-5 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol 
• 457653-07-5 benzyl 2-deoxy-3,5-O-(di-tert-butylsilylene)-1,4-dithio-D-erythro-pentofuranoside 
• 209048-67-9 1-[(2R)-3,5-O-(di-tert-butylsilylene)-2-deoxy-2-iodo-4-thio-β-D-ribofuranosyl]uracil 
• 209048-57-7 benzyl 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 
• 209048-59-9 1,4-anhydro-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-D-erythro-pent-1-enitol 

Downstream Products

• 166249-10-1 1-(5-O-trityl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)-3-(2-methoxyethoxymethyl)uracil 
• 166249-11-2 1-((2R,4S,5R)-4-Fluoro-5-trityloxymethyl-tetrahydro-thiophen-2-yl)-3-(2-methoxy-ethoxymethyl)-1H-pyrimidine-2,4-dione 
• 149359-04-6 1-[5-(4,4-dimethoxytrityl)-4-thio-β-D-ribofuranosyl]uracil 

Relevant academic research and scientific papers

Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues

Analogues of the canonical nucleosides required for nucleic acid synthesis have a longstanding presence and proven capability within antiviral and anticancer research. 4′-Thionucleosides, that incorporate bioisosteric replacement of furanose oxygen with sulfur, represent an important chemotype within this field. Established herein is synthetic capability towards a common 4-thioribose building block that enables access to thio-ribo and thio-arabino pyrimidine nucleosides, alongside their 4′-sulfinyl derivatives. In addition, this building block methodology is templated to deliver 4′-thio and 4′-sulfinyl analogues of the established anticancer drug gemcitabine. Cytotoxic capability of these new analogues is evaluated against human pancreatic cancer and human primary glioblastoma cell lines, with observed activities ranging from low μM to >200 μM; explanation for this reduced activity, compared to established nucleoside analogues, is yet unclear. Access to these chemotypes, with thiohemiaminal linkages, will enable a wider exploration of purine and triphosphate analogues and the application of such materials for potential resistance towards relevant hydrolytic enzymes within nucleic acid biochemistries.

Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics

Albomycins are peptidyl thionucleoside natural products that display antimicrobial activity against clinically important pathogens. Their structures are characterized by a thioheptose with atypical stereochemistry including a d-xylofuranose ring modified with a d-amino acid moiety. Herein it is demonstrated that AbmH is a pyridoxal 5′-phosphate (PLP)-dependent transaldolase that catalyzes a threo-selective aldol-type reaction to generate the thioheptose core with a d-ribofuranose ring and an l-amino acid moiety. The conversion of l-to d-amino acid configuration is catalyzed by the PLP-dependent epimerase AbmD. The d-ribo to d-xylo conversion of the thiofuranose ring appears according to gene deletion experiments to be mediated by AbmJ, which is annotated as a radical S-adenosyl-l-methionine (SAM) enzyme. These studies establish several key steps in the assembly of the thioheptose core during the biosynthesis of albomycins.

4’-THIONUCLEOSIDES AND OLIGOMERIC COMPOUNDS

The present invention provides modified oligomeric compounds and compositions of oligomeric compounds for use in the RNA interference pathway of gene modulation. The modified oligomeric compounds include siRNA and asRNA having at least one affinity modification.

A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds.

The coupling reactions of cyclic sulfides with a silylated pyrimidine nucleobase using a hypervalent iodine reagent were investigated. The reaction of silylated uracil with cyclic sulfide 12 using PhI=O gave the desired beta-anomer 14 in moderate yield. 4

Stereoselective synthesis of the β-anomer of 4′-thionucleosides based on electrophilic glycosidation to 4-thiofuranoid glycals

Three types of 4-thiofuranoid glycal with different 3,5-O-silyl protecting groups were prepared and their electrophilic glycosidation was investigated. The 3,5-bis-O-(tert-butyldimethylsilyl)-4-thiofuranoid glycal (5) was obtained through mesylation of 2-deoxy-4-thio-D-erythro-pentofuranose (4) and subsequent base-promoted elimination, while thermal elimination of sulfoxide derivatives was suitable for the preparation of 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) (9) and 3,5-O-(di-tert-butylsilylene) (11) 4-thioglycals. The glycosidation reactions of these 4-thioglycals were carried out, in the presence of either PhSeCl or NIS, by using silylated derivatives of uracil, thymine, cytosine, and N6-benzoyladenine. Among the three 4-thioglycals, 11 was found to be an excellent glycosyl donor, forming the desired β-anomer exclusively irrespective of the nucleobase employed.

The stereoselective synthesis of 4'-β-thioribonucleosides via the pummerer reaction

An efficient stereoselective synthesis of 4'-β-thioribonucleosides 14, 15, 27, and 30 using the Pummerer reaction as the key step is described. The Pummerer reaction of 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopro pyldisiloxane-1,3-di

4'-Thio-RNA: Synthesis, base pairing properties and interaction with dimerization initiation site of HIV-1

In the present paper, we describe the synthesis of a modified 9-mer oligonucleotide, 4'-S-r(UGUGCACCU) containing for the first time 4'-thio- guanosine units. This modified 9-mer was found to inhibit in vitro genomic RNA dimerization as well as the wild type RNA.

4'-Thio-β-D-oligoribonucleotides: Nuclease resistance and hydrogen bonding properties

The syntheses and the study of nuclease resistance and hydrogen bonding of modified oligoribonucleotides, i.e. 4'-thio-β-D-oligoribonucleotides (4'-S-RNA), are reported.

Synthesis and biological activity of 5 fluoro 4' thiouridine and some related nucleosides

The synthesis of a series of 4' thio 5 halogenopyrimidine nucleosides, including the 5 fluoro, chloro, bromo and iodo derivatives, has been carried out by condensation of the 2,4 bis O trimethylsilyl derivatives of the corresponding pyrimidine bases with the protected 4 thio D ribofuranosyl chloride. Among these, the α and β anomers of 4' thio 5 fluorouridine inhibited the growth of leukemia L1210 cells at concentrations of 4 x 10-7 and 2 x 10-7 M, respectively, and that of S. faecium at 4 x 10-9 and 6 x 10-10 M, respectively. These compounds retained marked activity against strains of S. faecium resistant to 10-3 M 5 fluorouracil or 5 fluorouridine. As determined in S. faecium cultures, 4' thio 5 fluorouridine decreased the total protein content of the cells more markedly than it did their RNA or DNA content. X Ray crystallography showed that substitution of sulfur for the oxygen in the carbohydrate ring markedly changes the conformation of that moiety.