3458-14-8

Usage

Uses

Used in Pharmaceutical Industry:
5'-Deoxythymidine is used as an antiviral agent for the treatment of various viral infections, particularly those caused by retroviruses. It competitively inhibits the influx of thymidine, thereby disrupting the viral replication process and helping to control the infection.
Used in Anticancer Applications:
In the field of oncology, 5'-Deoxythymidine is employed as a chemotherapeutic agent. It interferes with the synthesis of DNA in cancer cells, thereby inhibiting their proliferation and growth. This property makes it a valuable tool in the fight against various types of cancer.
Used in Antibacterial Applications:
5'-Deoxythymidine demonstrates antibacterial activity against certain bacteria, such as B. subtilis and S. aureus. It can be used as an antibacterial agent in the development of new antibiotics to combat bacterial infections.
Used in Research and Development:
Due to its unique properties and interactions with cellular nucleoside importers, 5'-Deoxythymidine is used as a research tool in various biological and medical studies. It helps researchers understand the mechanisms of DNA synthesis, viral replication, and other cellular processes.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of 5'-Deoxythymidine, novel drug delivery systems are being developed. These systems aim to improve the delivery of the compound to target cells, increasing its therapeutic potential and reducing potential side effects. Various organic and metallic nanoparticles have been explored as carriers for 5'-Deoxythymidine delivery in different applications.

Biological Activity

5'-deoxy thymidine has been used as a research tool for antiviral and anticancer studies. 5'-deoxy thymidine can be used to study the entry mechanism into human erythrocytes in comparison with other deoxythymidines. deoxythymidine, also named as thymidine, is the dna nucleoside t. deoxythymidine can pair with deoxyadenosine (a) in double-stranded dna. 5'-deoxy thymidine is a form of thymidine which had the hydroxyl group at the 5' position replaced with hydrogen [1]. 5'-deoxy thymidine (50 μg/ml) was effective against bacillus subtilis and staphylococcus aureus [1]. the mbc of 5'-deoxy thymidine was 50 μg/ml. 5'-deoxy thymidine has been used as an antibacterial agent in medical situations [1].thymidine has been phosphorylated at the hydroxyl group on carbon 5 of the ribose moiety before polymerization into dna. 5'-deoxy thymidine cannot be phosphorylated and used by dna polymerase in the synthesis of dna. in human erythrocytes, 5'-deoxy thymidine was readily and nonconcentratively uptaked by metabolism, and could be partially inhibited by nucleosides or inhibitors of nucleoside transport at micromolar concentrations [2].

references

[1] hatano a, nishimura m, souta i. impact of unnatural nucleosides on the control of microbial growth[j]. biocontrol science, 2009, 14(2): 55-60. [2] domin b a, mahony w b, koszalka g w, et al. membrane permeation characteristics of 5'-modified thymidine analogs[j]. molecular pharmacology, 1992, 41(5): 950-956.

Upstream product

• 63914-07-8 3'-O-toluoyl-β-thymidine 
• 21090-30-2 3'-O-acetylthymidine 
• 50-89-5 thymidine 
• 25905-51-5 5’-bromo-5’-deoxythymidine 
• 25905-50-4 5’-chloro-5’-deoxythymidine 
• 123884-10-6 5'-O-(phenoxythiocarbonyl)thymidine 
• 25953-14-4 1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 61168-97-6 2',5'-dideoxy-5-fluorouridine 
• 65-71-4 thymin 
• 626-48-2 6-Methyluracil 

Relevant academic research and scientific papers

Tetraaryldisilanes as a novel strategic radical reagent

Reactivity of 1,1,2,2-tetraaryldisilanes as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefins and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilanes showed moderate to good reactivities for these three types of radical reactions. Among some disilanes prepared, 1,1,2,2-tetraphenyldisilane is the most useful in view of its reactivity and ease of preparation.

1,1,2,2-tetraphenyldisilane as a diversified radical reagent

Reactivity of 1,1,2,2-tetraphenyldisilane as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefin and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilane showed moderate to good reactivities for these three types of radical reactions.

Novel Water-Soluble Organosilane Compounds as a Radical Reducing Agent in Aqueous Media

The development of novel water-soluble organosilane compounds and their application to radical reactions in water medium have been studied. A series of novel organosilane compounds having hydrophilic groups, such as an ether group and a hydroxy group in the side chain to bear hydrophilicity, were synthesized by the reaction of trichlorosilane or tetrachlorosilane and Grignard reagents. The reactivities of these organosilane compounds were studied in the radical reduction of 2-bromoethyl phenyl ether in ethanol in the presence of triethylborane under aerobic conditions. The results showed that diarylsilane was the most effective among them. The radical reduction of alkyl and aryl halides with diarylsilane was applied to a reaction in aqueous media, which gave the corresponding reduction product in good yields. Thus, the present organosilanes are very useful for the reduction of water-soluble substrates, such as halo sugars in water.

Synthesis of novel 3'-C-(hydroxymethyl)thymidines and oligodeoxynucleotide analogues containing compressed 3'-C-hydroxymethyl-linked phosphodiester backbones

Lombardo methylenation of the novel 2'-deoxy-3'-ketonucleosides 4 afforded 2',3'-dideoxy-3'-C-methylene nucleosides 5, which were subjected to catalytic dihydroxylation reactions. In the case of 5'-deoxynucleoside 5a, a 1:1 mixture of 3'-C-hydroxymethyl diastereoisomers 6a and 7a was obtained, whereas the 5'-O-silylated nucleoside 5b afforded 3'-C- (hydroxymethyl)thymidine derivative 6b as the only product. Sharpless asymmetric dihydroxylation of 5a proceeded in low yield to give 6a and 7a as a 10:3 mixture. 5'-O-Silylated nucleoside 6b was converted into the phosphoramidite synthon 9, which was applied in automated syntheses of oligodeoxynucleotides containing novel compressed 3'-C-hydroxymethyl linked phosphodiester backbones.

Facile Synthesis of 3'-O-Methylthymidine and 3'-Deoxythymidine and Related Deoxygenated Thymidine Derivative: A New Method for Selective Deoxygenation of Secondary Hydroxy Groups

This paper deals with convenient synthesis of 3'-O-methylthymidine (2) and 3'-deoxythymidine (3), which involve Ag2O-promoted methylation and Barton-Robins reductive deoxygenation, respectively.New methods for the regioselective 3'- and 5'-deoxygenation of thymidine have also been developed.Namely, compound 3 was synthesized by the 3',5'-O-diacylation of thymidine with phenyl chlorothionoformate (PTCF) followed by the selective 3'-reduction with tributyltin hydride and successive alkaline hydrolysis. 5'-Deoxythymidine (18) was obtained by the 5'-selective acylation of thymidine with PTCF followed by reduction with tributyltin hydride.