19316-85-9

Basic information

• Product Name: 5'-AZIDO-5'-DEOXYTHYMIDINE
• Synonyms: 5'-AZIDO-5'-DEOXYTHYMIDINE;5'-AZIDO-5'-DEOXY-D-THYMIDINE;1-((2R,4S,5R)-5-(azidoMethyl)-4-hydroxytetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione;5'-AZT;NSC 254064
• CAS NO: 19316-85-9
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24
• Mol File: 19316-85-9.mol
• Article Data: 44

Chemical Properties

• Melting Point: 164-166℃
• Appearance: /
• CAS DataBase Reference: 5'-AZIDO-5'-DEOXYTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-AZIDO-5'-DEOXYTHYMIDINE(19316-85-9)
• EPA Substance Registry System: 5'-AZIDO-5'-DEOXYTHYMIDINE(19316-85-9)

Safety Data

• Hazardous Substances Data: 19316-85-9(Hazardous Substances Data)

Usage

Uses

5’Azido-(5’deoxy)thymidine is a potential thymidine-based inhibitor of mycobacterium tuberculosis monophosphate kinase (TMPKmt), an essential enzyme to DNA replication of tuberculosis mycobacterium.

Upstream product

• 7766-50-9 1-undecen-11-ylbromide 
• 25953-14-4 1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 132101-17-8 5′-azide-3′-O-tert-butyldimethylsilyl deoxythymidine 
• 171563-32-9 5′-O-mesyl-3′-O-tert-butyldimethylsilyl deoxythymidine 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 288-32-4 1H-imidazole 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 558-13-4 carbon tetrabromide 
• 50-89-5 thymidine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 149284-20-8 methyl 5-azido-2,5-dideoxy-β-D-erythro-pentofuranoside 
• 158603-53-3 methyl 3-O-acetyl-5-azido-2,5-dideoxy-β-D-erythro-pentofuranoside 
• 65-71-4 thymin 

Downstream Products

• 108895-41-6 9-<2-Deoxy-3-O-methanesulphonyl-5-O-(4-monomethoxytrityl)-β-D-threo-pentofuranosyl>adenine 
• 141690-79-1 6-N,N-Dibenzoyl-9-<2-deoxy-3-O-methanesulphonyl-5-O-(4-monomethoxytrityl)-β-D-threo-pentofuranosyl>adenine 
• 108895-39-2 9-<5-O-(monomethoxytrityl)-2-deoxy-β-D-threo-pentofuranosyl>adenine 
• 13276-53-4 9-(2'-deoxy-β-D-threo-ribofuranosyl)-adenine 
• 357399-10-1 N⁶-benzoyl-3',5'-diamino-2',3',5'-trideoxyadenosine 
• 125943-99-9 N⁶-benzoyl-3',5'-diazido-2',3',5'-trideoxyadenosine 
• 556826-38-1 Methanesulfonic acid (2R,3R,5R)-5-(6-dibenzoylamino-purin-9-yl)-2-methanesulfonyloxymethyl-tetrahydro-furan-3-yl ester 
• 556826-40-5 N-(9-{4-amino-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide 
• 556826-41-6 C₅₃H₄₅N₇O₆S 
• 357399-11-2 C₅₃H₄₆N₈O₅S 
• 1046354-53-3 5'-deoxy-5'-[4-(4-fluorophenyl)-(1,2,3)triazol-1-yl]thymidine 
• 1046354-49-7 5'-deoxy-5'-[4-phenyl-(1,2,3)triazol-1-yl]thymidine 
• 1046354-57-7 5'-deoxy-5'-[4-(4-methoxyphenyl)-(1,2,3)triazol-1-yl]thymidine 

Relevant articles and documents

Lipid-conjugated oligonucleotides via click chemistry efficiently inhibit hepatitis C virus translation

Conjugation of a lipid moiety via click chemistry potentiates the cellular uptake of oligonucleotides and allows their intracellular delivery. These nontoxic lipid conjugates efficiently inhibit hepatitis C virus internal ribosome entry site (IRES)-mediated translation in human hepatic Huh7 cells. The biological activity of the lipid-conjugated oligonucleotides is not affected by the presence of serum.

Microwave-assisted synthesis of a triazole-linked 3′-5′ dithymidine using click chemistry

Synthesis of a triazole-linked 3′-5′ thymidine dimer making use of 1,3-dipolar cycloaddition is described. The azido-precursor was obtained by regioselective chlorination of thymidine, followed by azidation. The second precursor, a propargyl derivative, was obtained by selective 3′-O-alkylation of thymidine. Two 'click systems' were compared to obtain the desired dimer. These reactions were performed by microwave irradiation.

Synthesis and characterization of ferrocene-labeled oligodeoxynucleotides

Using a facile on-column derivatization procedure, oligodeoxynucleotides (ODNs) are labeled with a ferrocene derivative at specific sites. A Sonagashira cross-coupling reaction, using Pd(PPh3)4 and CuI, links ferrocene propargylamide

Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues

The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.

Design, Synthesis and Biological Evaluation of Novel Anthraniloyl-AMP Mimics as PQS Biosynthesis Inhibitors against Pseudomonas aeruginosa Resistance

The Pseudomonas quinolone system (PQS) is one of the three major interconnected quorum sensing signaling systems in Pseudomonas aeruginosa. The virulence factors PQS and HHQ activate the transcription regulator PqsR (MvfR), which controls several activiti

Synthesis and in vitro anticancer activity of new gemcitabine-nucleoside analogue dimers containing methyltriazole or ester-methyltriazole linker

Two series of novel gemcitabine-nucleoside analogue dimers were synthesized using the ‘click’ chemistry approach. In the first series of dimers (21–30), the nucleoside units were connected with a stable methyltriazole 4N-3′(or 5′)C linker whereas in the second series (31–40) with a cleavable ester-methyltriazole 4N-3′(or 5′)C linker. Dimers 21–40 were evaluated for their cytotoxic activity in five human cancer cell lines such as cervical (HeLa), nasopharyngeal (KB), lung (A549), brain (U87), liver (HepG2) and normal dermal fibroblast cell line (HDF) using the sulforhodamine B (SRB) assay. Compound 29 comprising two gemcitabine (dFdC) units exhibited the highest activity among dimers 21–30. The activity of compound 29 was higher than that of dFdC in all the studied cancer cell lines. A similar order of activity was observed for compounds 25, 28, and 30. The best activity among all the dimers synthesized was displayed by compound 39, comprising two gemcitabine units with a cleavable linker. The activity of compound 39 was 5 to 9 times higher than that of dFdC, depending on the cell line. In addition, marked cytotoxic activity was shown by compounds 31, 36, 38, and 40.