58699-62-0

Usage

Uses

Used in Pharmaceutical Industry:
3'-azido-3'-deoxyadenosine is used as an antiviral agent for the treatment of HIV/AIDS. It is employed to inhibit the activity of reverse transcriptase, thereby preventing the replication of the virus and reducing the viral load in patients.
Used in Combination Antiretroviral Therapy:
AZT is used as a key component in combination antiretroviral therapy for HIV/AIDS. It is combined with other antiretroviral drugs to enhance the treatment's effectiveness and manage the disease's progression more effectively.
Used in Research and Development:
3'-azido-3'-deoxyadenosine is also utilized in research and development for the study of HIV/AIDS and the development of new antiviral drugs and therapies. Its mechanism of action provides valuable insights into the understanding of viral replication and the design of novel therapeutic strategies.

Upstream product

• 216976-72-6 Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 917239-34-0 9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine 
• 103597-09-7 9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine 
• 695183-20-1 3'-azido-3'-deoxy-2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 
• 889126-06-1 2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose 
• 917239-33-9 9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine 
• 120143-22-8 3-azido-1,2-di-O-acetyl-5-O-(p-toluoyl)-3-deoxy-D-ribofuranose 
• 118525-25-0 9-[2',5'-bis-(O-tert-butyldimethylsilyl)-β-D-xylofuranosyl]-9H-adenine 
• 86734-95-4 9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 
• 216976-71-5 Benzoic acid (3R,4R,5S)-4-azido-2-methoxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-70-4 Carbonic acid (3aR,5S,6R,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester methyl ester 
• 114861-16-4 Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 216976-56-6 ((3aR,5S,6R,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 

Downstream Products

• 2504-55-4 3'-amino-3'-deoxyadenosine 
• 946497-29-6 3'-[N-(tert-butoxycarbonyl)-O-methyl-L-tyrosyl]amido-3'-deoxyinosine 
• 53-79-2 puromycin 
• 57183-05-8 tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate 
• 58-60-6 3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine 
• 1290142-96-9 2',5'-O-dimethyl-3'-(N-[Nα-(9-fluorenylmethoxycarbonyl)-L-(p-methoxyphenylalanyl)amino])-3'-deoxyadenosine 
• 1290142-91-4 3'-deoxy-2',5'-O,O-dimethyl-3'-N-(L-p-methoxyphenylalanyl)aminoadenosine 
• 1290142-97-0 3'-deoxy-2'-O-methyl-3'-(N-(L-p-methoxyphenylalanyl)amino)adenosine 
• 1290142-98-1 3'-deoxy-5'-O-methyl-3'-(N-(L-p-methoxyphenylalanyl)amino)adenosine 
• 1384456-58-9 3'-azido-3'-deoxy-5'-O-(tert-butyldiphenylsilyl)-2'-O-(N-tert-butoxycarbonyl-S-tritylcysteinyl)adenosine 
• 1384456-59-0 3'-azido-3'-deoxy-2'-O-(S-tritylcysteinyl)adenosine 
• 1384456-54-5 3'-azido-5'-O-(tert-butyldiphenylsilyl)-3'-deoxyadenosine 

Relevant academic research and scientific papers

NUCLEIC ACID POLYMERS

A nucleic acid polymer comprising 8 to 50 nucleoside subunits linked by intersubunit linkages, wherein the nucleic acid polymer comprises (A) one or more 3'-5' thiophosphoramidate intersubunit linkage and the remaining intersubunit linkages are 3'-5' thiophosphate intersubunit linkages and/or (B) at least 40% of the nucleoside subunits contain a 2'-MOE substituent. Those nucleic acid polymers are useful in the treatment of a viral infection, more specifically Hepatitis B virus and/or Hepatitis D virus.

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

MODIFIED NUCLEOSIDE PHOSPHORAMIDITES

The present disclosure relates to compounds and compositions containing 5'-phosphoramidite nucleoside monomers of formulae (I) and (II), and methods of making and use, wherein the substituents are as defined in the appended claims.

MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE IN TAUOPATHIES

Oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of 5 making and use against Alzheimer disease and other tauopathies are disclosed.

MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE

Modified oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of making and use, e.g., against HBV are disclosed.

Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase

Non-hydrolyzable substrate analogs for tRNA-dependent amidotransferase, 2′- or 3′-aspartyl or -glutamyl adenosine, were synthesized from adenosine without protection of the adenine base. The hydroxyl groups of adenosine were selectively protected, followed by a series of oxidation/reductions to alter the stereochemistry. DFT calculations revealed the driving forces for the ketone hydrate formation at C-2′, but not the C-3′ carbon during the oxidation step. Subsequently, triflation and azide replacement yielded azidoadenosines, which were coupled to protected amino acids after deprotection and reduction. After global deprotection, the target substrate analogs were obtained in 2-14% overall yields from adenosine.

Facile and rapid access to inosine puromycin analogues through the use of adenylate deaminase

To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3′-azidodeoxyadenosine derivatives using adenylate deaminase for the quantita

Synthesis of N6-Substituted 3′-ureidoadenosine derivatives as highly potent agonists at the mutant A3 adenosine receptor

Several N6-substituted 3′-ureidoadenosine derivatives were efficiently synthesized starting from D-glucose for the development of H272E mutant A3 adenosine receptor (AR) agonists. Among compounds tested, 3′-ureido-N6-(3-iodobenzyl)adenosine (2c) exhibited

Synthesis and anti-HIV activity of β-D-3′-azido-2′, 3′-unsaturated nucleosides and β-D-3′-azido-3′- deoxyribofuranosylnucleosides

□ Since the discovery of 3′-azido-3′-deoxythymidine (AZT) and 2′,3′-didehydro-2prime;,3′-dideoxythymidine (d4T) as potent and selective inhibitors of the replication of human immunodeficiency virus (HIV), there has been a growing interest for the synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides with electron withdrawing groups on the sugar moiety. Here we described an efficient method for the synthesis of such nucleoside analogs bearing structural features of both AZT and d4T. The hey intermediate, 3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3- deoxy-D-ribofuranose, 5 was synthesized from commercially available D-xylose in five steps, from which a series of pyrimidine and purine nucleosides were synthesized in high yields. The resultant protected nucleosides were converted to target nucleosides using appropriate chemical modifications. The final nucleosides were evaluated as potential anti-HIV agents. Copyright Taylor & Francis Group, LLC.

Synthesis of 3'-azido- and 3'-amino-3'-deoxyadenosine in both enantiomeric forms

Aminosugar nucleosides are important bioactive molecules of which puromycin, a derivative of 3'-amino-3'-deoxyadenosine, is one of the most important examples. Some azidosugar nucleosides, the synthetic precursors of the corresponding aminosugar compounds, are known to be active against HIV reverse transcriptase. We are interested in comparing the bioactivity of D- and L-enantiomers of such nucleosides. Here, the synthesis of both D- and L- enantiomers of 3'-azido- and 3'-amino-3'-deoxyadeonsine, respectively, is described. It begins with the introduction of the nitrogen functionality through a substitution reaction with inversion at C-3 of a D- or L-xylose derivative, respectively. The azidosugar is converted into an appropriate glycosyl donor which is the submitted to a glycosidation reaction according to Vorbruggen. Deprotection affords 3'azido-3'-deoxy-D/L-adenosine, our potentially antiviral target compounds, and reduction of the azido substituent leads to the aminosugar target molecules.