7150-83-6

Usage

Uses

Used in Antiviral Applications:
1-(2-deoxy-5-thiopentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione is used as an antiviral agent for its ability to inhibit the replication of certain viruses, such as HIV and herpes simplex virus. It achieves this by interfering with the synthesis of viral DNA or RNA, thus preventing the spread of the virus within the host.
Used in Anticancer Applications:
In the field of oncology, 1-(2-deoxy-5-thiopentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione is used as a potential anticancer agent. It has demonstrated the ability to inhibit the growth of certain cancer cells, making it a subject of ongoing research for the development of new cancer treatments.
Used in Pharmaceutical Research:
1-(2-deoxy-5-thiopentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione is used as a research compound for exploring its therapeutic potential in the development of new antiviral and anticancer treatments. Its unique properties as a modified nucleoside analog make it a valuable candidate for further investigation into its mechanisms of action and potential applications in medicine.

Upstream product

• 6959-79-1 3'-O-acetyl-5'-acetylthio-5'-deoxythymidine 
• 174466-94-5 Thiobenzoic acid S-[(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 132628-15-0 9-(4-methoxyphenyl)-9H-xanthene-9-thiol 
• 144944-94-5 5'-S-acetyl-5'-deoxy-5'-thiothymidine 
• 25953-14-4 1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 59211-00-6 3'-O-Acetyl-5'-O-mesyl-thymidin 
• 21090-30-2 3'-O-acetylthymidine 
• 14046-57-2 3'-O-acetyl-5'-deoxy-5'-iodothymidine 
• 50-89-5 thymidine 
• 7253-19-2 5'-O-(p-toluenesulfonyl)thymidine 
• 84364-98-7 2-[(2S,3S,5R)-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-isothiourea; hydriodide 

Downstream Products

• 84364-97-6 5'-S-dimethylarsino-5'-thio-5'-deoxythymidine 
• 65-71-4 thymin 
• 167147-55-9 5'-[(3,4-dibenzyloxy)benzylthio]-5'-deoxythymidine 
• 144846-10-6 5'-(12-trityloxydodecylthio)-5'-deoxythymidine 
• 500775-64-4 5'-S-(4,4'-dimethoxytrityl)-5'-thiothymidine 3'-(2-cyanoethyl-diisopropylphosphoramidite) 
• 177738-46-4 5'-S-(4,4'-dimethoxytrityl)-5'-thiothymidine 

Relevant academic research and scientific papers

Efficient solid phase synthesis of cleavable oligodeoxynucleotides based on a novel strategy for the synthesis of 5′-S-(4,4′-dimethoxytrityl)- 2′-deoxy-5′-thionucleoside phosphoramidites

The incorporation of a specific cleavage site into an oligodeoxynucleotide can be achieved by utilizing the four 5′-S-(4,4′-dimethoxytrityl)- 2′-deoxy-5′-thionucleoside 3′-(2-cyanoethyl diisopropylphosphoramidites) 5 and 15a-c (Fig.1). Based on the silver

Kinetic and Theoretical Studies on the Mechanism of Alkaline Hydrolysis of DNA

The reaction mechanism of alkaline hydrolysis of DNA has been investigated by kinetic analysis and density-functional-theory calculation. The rates of hydrolysis of thymidine 3′-monophosphate esters (including thymidylyl(3′-5′)thymidine (Tp-OT)) monotonically decrease as the leaving groups get poorer. According to the theoretical calculation in which the solvent effects are incorporated, no intermediate is formed in the course of the reaction. In the alkaline hydrolysis of the activated Tp-OT analogues having good leaving groups, the 3′,5′-cyclic monophosphate of thymidine is concurrently formed through the intramolecular attack by the 5′-alkoxide ion. In the hydrolysis of the native dinucleotide, however, this side reaction does not occur, since the transition state leading to the departure of its poor leaving group cannot be formed due to conformational restraint. These arguments are supported by the theoretical analysis on the hydrolysis of both dimethyl phosphate and its O(bridging)→S substituted analogue.

Dinucleoside monophosphate analogues containing disulfide linkages

Two dinucleoside monophosphate analogues containing disulfide linkages (1 and 2) have been prepared for incorporation into oligonucleotides. The modified oligomers will be tested for their potential as antisense agents.

5'-S-NUCLEOSIDE TRIPHOSPHATES. SYNTHESIS AND SUBSTRATE PROPERTIES IN TESTS WITH DNA POLYMERASES

With the aim of studying the properties of DNA polymerases in the biosynthesis of DNA we have synthesized the 5'-S-triphosphates of 5'-mercapto-5'-deoxythymidine and of 5'-mercapto-3',5'-dideoxythymidine from 3'-O-acetylthymidine and 3'-deoxythymidine, respectively.A study in cell-free systems with DNA polymerases of the triphosphate compounds obtained showed that 5'-mercapto-5'-deoxythymidine 5'-S-triphosphate possessed weak substrate properties, being included only once in the 3'-end of a growing DNA chain when the process was catalyzed by DNA polymerase I and AMV reverse transcriptase.At the same time, neither DNA polymerase α from human placenta, nor DNA polymerase β from rat liver, nor HIV reverse transcriptase interacted with these compounds at all. 5'-Mercapto-3',5'-dideoxythymidine 5'-triphosphate did not extend a DNA chain on catalysts by any of the above-mentioned enzymes.Possible reason for the sharp fall in the substrate properties of the compounds synthesized as compared with the natural substrates of DNA polymerases are discussed.