4099-81-4

Usage

Uses

Used in Pharmaceutical Industry:
5'-IODO-5'-DEOXYADENOSINE is used as an antiviral agent for the treatment of viral infections, particularly ocular herpes simplex infections. It works by inhibiting viral DNA synthesis and is effective in reducing the severity and duration of the infection.
Used in Research and Development:
In the field of research, 5'-IODO-5'-DEOXYADENOSINE is used as an important precursor for the synthesis of nucleotides, sugar nucleosides, and other biologically active substances. Its unique structure allows scientists to explore its potential applications in the development of new antiviral drugs and therapies.
Used in Drug Synthesis:
5'-IODO-5'-DEOXYADENOSINE is also used as a key intermediate in the synthesis of various pharmaceutical compounds, including other antiviral medications and cancer treatments. Its role as a precursor enables the development of novel drugs with improved efficacy and reduced side effects.

Upstream product

• 58-61-7 adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 30685-66-6 5'-iodo-5'-deoxy-2',3'-O-isopropylideneadenosine 

Downstream Products

• 20535-04-0 9-(Desoxy-5 β-D-erythro-pent-4-enofuranosyl)adenine 
• 68200-73-7 6-N-benzoyl-9-(5-deoxy-β-D-erythro-pent-4-enofuranosyl)adenine 
• 4754-39-6 5'-deoxyadenosine 

Relevant academic research and scientific papers

Characterization and Mechanistic Study of the Radical SAM Enzyme ArsS Involved in Arsenosugar Biosynthesis

Arsenosugars are a group of arsenic-containing ribosides that are found predominantly in marine algae but also in terrestrial organisms. It has been proposed that arsenosugar biosynthesis involves a key intermediate 5′-deoxy-5′-dimethylarsinoyl-adenosine (DDMAA), but how DDMAA is produced remains elusive. Now, we report characterization of ArsS as a DDMAA synthase, which catalyzes a radical S-adenosylmethionine (SAM)-mediated alkylation (adenosylation) of dimethylarsenite (DMAsIII) to produce DDMAA. This radical-mediated reaction is redox neutral, and multiple turnover can be achieved without external reductant. Phylogenomic and biochemical analyses revealed that DDMAA synthases are widespread in distinct bacterial phyla with similar catalytic efficiencies; these enzymes likely originated from cyanobacteria. This study reveals a key step in arsenosugar biosynthesis and also a new paradigm in radical SAM chemistry, highlighting the catalytic diversity of this superfamily of enzymes.

Synthesis and hybridizing property of oligonucleotides including 2′-C,4′-Cethyleneoxy- bridged 2′-deoxyadenosine with an exocyclic methylene unit

2′,4′-Bridged nucleic acids (2′,4′-BNAs) are of interest because oligonucleotides that include them have excellent duplex-forming capability and high nuclease resistance compared to natural oligonucleotides. We have recently developed 2′-C,4′-C-ethyleneoxy-bridged thymidine with an exocyclic methylene unit (methylene-EoDNA-T) as a novel 2′,4′-BNA analog. Oligonucleotides that include methylene-EoDNA-T have marked hybridizing capability, nuclease resistance, and in vitro gene-silencing potency. In the present study, we designed and synthesized a 2′-deoxyadenosine analog of methylene-EoDNA (methylene-EoDNA-A), and incorporated it into oligonucleotides. The results of melting temperature (Tm) analysis of duplexes formed from methylene-EoDNA-A-modified oligonucleotides indicated that the hybridizing capability with regard to complementary DNA was almost the same or slightly higher than that of natural DNA. Moreover, methylene-EoDNA-A:methylene-EoDNA-T base pairs increased the thermal stability of DNA duplexes compared to that of DNA duplexes containing methylene-EoDNA-A- or methylene-EoDNA-T-modification in one strand.

Nicotinamide-Containing Di- and Trinucleotides as Chemical Tools for Studies of NAD-Capped RNAs

We report the chemical synthesis of a set of nicotinamide adenine dinucleotide (NAD) cap analogues containing chemical modifications that reduce their susceptibility to NAD-RNA-degrading enzymes. These analogues can be incorporated into transcripts in a similar way as NAD. Biochemical characterization of RNAs carrying these caps with DXO, NudC, and Nudt12 enzymes led to the identification of compounds that can be instrumental in unraveling so far unaddressed biological aspects of NAD-RNAs.

8-substituent-N-methyl-4'-azido-vidarabine analogue and preparation method thereof

The invention discloses a 8-substituent-N-methyl-4'-azido-vidarabine analogue and a preparation method thereof and belongs to the field of pharmaceutical chemistry. The compound has a structural general formula represented by a formula shown in the description, wherein R is Cl, Br or CH3. The 8-substituent-N-methyl-4'-azido-vidarabine analogue is prepared through subjecting adenosine, which serves as a starting raw material, to reactions such as iodination, double-bond forming, azidation, hydroxyl and amino protection, hydroxyl and amino deprotection, Dimorth rearrangement, 8-bit halogenation and methylation sequentially. The 8-substituent-N-methyl-4'-azido-vidarabine analogue is a good potential antitumor drug, the preparation method is simple in operation, the raw materials are cheap, and the cost is low, so that large-scale production is easy to achieve.

Large-scale, protection-free synthesis of Se-adenosyl-l-selenomethionine analogues and their application as cofactor surrogates of methyltransferases

S-Adenosyl-l-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-l-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-l-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to-selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.

First example of phosphoramidate approach applied to a 4′-substituted purine nucleoside (4′-Azidoadenosine): Conversion of an inactive nucleoside to a submicromolar compound versus hepatitis C virus

We report on the synthesis of the anti hepatitis C virus (HCV) agent 4′-azidoadenosine (1) and the application of the phosphoramidate ProTide technology to this nucleoside. The synthesis of 1 was achieved through an epoxide intermediate followed by regio- and stereoselective ring opening by azidotrimethylsilane in the presence of a Lewis acid. Compound 1 did not inhibit HCV replication in cell culture at concentrations up to 0.1 mM. However, a submicromolar active agent could be derived from 1 by the application of the ProTide technology. All the phosphoramidates prepared were L-alanine derivatives with variations in the aryl moiety and in the ester part of the amino acid. The benzyl ester and the 1-naphthyl phosphate (18) had the best activity in replicon assay. Phosphoramidates (18-21) achieved a significant improvement in antiviral potency over the parent nucleoside (1) with no increase in cytotoxicity.

Antiviral phosphoramidates

The invention provides novel nucleoside compounds of formula I wherein R1, R2a, R2b, R3, R4, R5, R6, R8a, R9 and R10 are as defined herein which are useful for the treatment of Hepatitis C Virus (HCV) mediated diseases. The invention further provides methods for treatment or prophylaxis of HCV mediated diseases with compounds of formula I and pharmaceutical compositions comprising these compounds,

Synthetic Approaches towards Nucleocidin and Selected Analogues; anti-HIV Activity in 4'-Fluorinated Nucleoside Derivatives

Nucleocidin 1 has been synthesised from the adenosine derivative 4 via the intermediacy of the dihalogeno compound 9.The latter compound showed slight but significant activity against HIV-infected cells while the isomer 10 and the monohalogeno compound 60 were inactive.Synthetic approaches towards other 4'-fluorinated nucleoside derivatives are also described.The epimeric 4'-fluorinated nucleosides 26 and 27 displayed similar activity against HIV-infected cells to that observed for the dihalogenated compound 9.