215176-58-2

Usage

Uses

Used in Pharmaceutical Industry:
3'-Azido-3'-deoxy-5-Methyuridine is used as an antiviral agent for the treatment of HIV/AIDS. It acts as a potent and selective inhibitor of HIV-1 replication by blocking the activity of reverse transcriptase, an enzyme essential for the virus's replication process. This helps in reducing the viral load and slowing down the progression of the disease.
Additionally, AZT is also used as a component in combination therapies, such as highly active antiretroviral therapy (HAART), which has significantly improved the prognosis and life expectancy of HIV/AIDS patients. The use of AZT in combination with other antiretroviral drugs helps in preventing the development of drug resistance and enhances the overall effectiveness of the treatment.

Upstream product

• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 6022-96-4 5-O-benzoyl-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 215176-57-1 3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine 
• 532-20-7 D-xylofuranose 
• 103597-08-6 1,2-di-O-acetyl-3-azido-3-deoxy-5-O-benzoyl-β-D-ribofuranose 
• 91363-90-5 ((3aR,5S,6R,6aR)-6-azido-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 94795-72-9 1,2-O-isopropylidene-5-O-benzoyl-3-O-trifluoromethanesulfonyl-α-D-xylofuranose 
• 65-71-4 thymin 
• 75096-64-9 3-Azido-3-deoxy-1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-β-D-ribofuranose 
• 120042-40-2 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 

Downstream Products

• 607351-45-1 1-(3-azido-3-deoxy-5-O-trityl-β-D-ribofuranosyl)thymine 
• 1519007-46-5 3'-deoxy-3'-(4-phenyl-1,2,3-triazol-1-yl)-5-methyluridine 
• 607351-46-2 O-2,2'-anhydro-1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 99614-77-4 3'-azido-3'-deoxythymidine 
• 132776-25-1 1-(3-azido-2,3-dideoxy-2-fluoro-5-O-trityl-β-D-ribofuranosyl)thymine 
• 128269-50-1 1-(3-azido-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 127840-94-2 1-(3-azido-2-fluoro-2,3-dideoxy-β-D-ribofuranosyl)thymine 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5- methyluridine

An efficient protocol has been developed for the synthesis of a small library of 3'-deoxy-3'- (4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3- dipolar cycloaddition reaction of 3'-azido-3'-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3'-azido-3'-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K2CO3 in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, 1H-, 13C NMR spectra, and high-resolution mass spectra) data analysis.

Mycobacterium tuberculosis thymidine monophosphate kinase inhibitors: Biological evaluation and conformational analysis of 2′- and 3′-modified thymidine analogues

Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) has recently been introduced as a potential target for the structure-based design of anti-tuberculosis drugs. Based on the TMPKmt X-ray structure and previous S.A.R. studies, we synthesised the nucleoside analogues 3a-b, 6a-b, 7a-b, and 8a-b, modified in 2′- and 3′-position of the ribofuranose ring moiety. To our surprise, these analogues showed only moderate binding affinity (i.e. Ki between 118 and 1260 μM). This prompted us to investigate the conformational features of these nucleosides. We concluded that compounds of this series, especially 8a-b, are strongly biased towards the "Northern" furanose ring conformation, whereas X-ray crystallography reveals a preference of TMPKmt for the opposite "Southern" conformers. This paper covers the synthesis, biological evaluation and conformational features (i.e. preferred ring puckering) of the 2′- and 3′-modified dT analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase

A number of 2′- and 3′-modified thymidine 5′-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2′-halogeno substituent and a 3′-azido function are the most favorable leads for further development of potent inhibitors of this enzyme.