128496-10-6

Usage

Uses

Used in Pharmaceutical Industry:
3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine is utilized as a key intermediate in the synthesis of nucleoside analogs for the development of antiviral and anticancer drugs. Its unique structure allows for the creation of compounds with enhanced therapeutic properties and selectivity, making it a valuable asset in medicinal chemistry research.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine serves as a versatile building block for the design and synthesis of novel nucleoside-based drugs. Its incorporation into drug candidates can potentially improve their efficacy, safety, and pharmacokinetic profiles.
Used in Biochemical Research:
3',5'-Bis-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine is employed in biochemical studies to investigate the interactions between nucleic acids and various proteins and enzymes. This research can provide insights into the mechanisms of action of nucleoside analogs and contribute to the understanding of their biological effects.

Upstream product

• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 491594-58-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranose 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 66-22-8 uracil 

Downstream Products

• 1145869-36-8 1-(4'-azido-3'-O-benzoyl-2'-deoxy-2'-fluoro-5'-iodo-β-D-arabinofuranosyl)uracil 
• 1333126-30-9 1-(4-azido-2-deoxy-2-fluoro-3-O-benzoyl-5-O-(3-chlorobenzoyl)-β-D-arabinofuranosyl)uracil 
• 122757-53-3 1-(2,3-dideoxy-2-fluoro-β-D-glycero-pent-2-enofuranosyl)cytosine 
• 128496-11-7 1-<2-deoxy-2-fluor-3-O-(methylsulfonyl)-5-O-trityl-β-D-arabinofuranosyl>)uracil 
• 128496-13-9 2',3'-dideoxy-2',3'-didehydro-3'-fluoro-5'-O-trityluridine 
• 128496-16-2 1-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)uracil 
• 128496-17-3 1-(2,3-dideoxy-2,3-difluoro-5-O-trityl-β-D-arabinofuranosyl)uracil 
• 128496-12-8 (1R,9S,10R,12S)-12-Fluoro-10-trityloxymethyl-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one 
• 128496-20-8 1-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)cytosine 
• 122757-52-2 2',3'-dideoxy-2',3'-didehydro-3'-fluorouridine 
• 69123-94-0 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)uracil 

Relevant academic research and scientific papers

3-methyl uridine and 4-methyl cytidine nucleoside compound, synthetic method and its pharmaceutical use

The invention discloses a 3-methyluridine and 4-methylcytidine nucleosides compound and a synthesis method and pharmaceutical application thereof, belonging to the field of medicinal chemistry. The compound has a structural formula as shown in the specification. The compound has the effects of simultaneously modifying sugar rings and basic groups, increasing the activity of the compound and reducing the toxicity, provides a good application prospect for development of like medicines and can be applied to preparation of anti-HBV (Hepatitis B virus) medicines. The synthesis method is simple and feasible and provides conditions for mass synthesis of the compound.

Synthesis of new 2′-deoxy-2′-fluoro-4′-azido nucleoside analogues as potent anti-HIV agents

We prepared 1-(4′-azido-2′-deoxy-2′-fluoro-β-d- arabinofuranosyl)cytosine (10) and its hydrochloride salt (11) as potential antiviral agents based on the favorable antiviral profiles of 4′-substituted nucleosides. Compounds 10 and 11 were synthesized from 1,3,5-O-tribenzoyl-2-deoxy-2-fluoro-d-arabinofuranoside in multiple steps, and their structures were unequivocally established by IR, 1H NMR, 13C NMR, and 19F NMR spectroscopy, HRMS, and X-ray crystallography. Compounds 10 and 11 exhibited potent anti-HIV-1 activity (EC50: 0.3 and 0.13 nM, respectively) without significant cytotoxicity in concentrations up to 100 μM. Compound 11 exhibited extremely potent anti-HIV activity against NL4-3 (wild-type), NL4-3 (K101E), and RTMDR viral strains, with EC50 values of 0.086, 0.15, and 0.11 nM, respectively. Due to the high potency of 11, it was also screened against an NIH Reagent Program NRTI-resistant virus panel containing eleven mutated viral strains and for cytotoxicity against six different human cell lines. The results of this screening indicated that 11 is a novel NRTI that could be developed as an anti-AIDS clinical trial candidate to overcome drug-resistance issues.

Synthesis and anti-HIV activity of 2′-deoxy-2′-fluoro-4′-C-ethynyl nucleoside analogs

Based on the favorable antiviral profiles of 4′-substituted nucleosides, novel 1-(2′-deoxy-2′-fluoro-4′-C-ethynyl-β-d-arabinofuranosyl)-uracil (1a), -thymine (1b), and -cytosine (2) analogs were synthesized. Compounds 1b and 2 exhibited potent anti-HIV-1 activity with IC50 values of 86 and 1.34 nM, respectively, without significant cytotoxicity. Compound 2 was 35-fold more potent than AZT against wild-type virus, and also retained nanomolar antiviral activity against resistant strains, NL4-3 (K101E) and RTMDR. Thus, 2 merits further development as a novel NRTI drug.

Synthesis of some 2′-fluoro-2′-deoxy-3′-C-ethynyl and 3′-C-vinyl-β-D-lyxofuranosyl nucleosides

1-(2-Fluoro-2-deoxy-β-D-arabinofuranosyl)uracil (5) and 1-(2-fluoro-2-deoxy-β-D-arabinofuranosyl)cytosine (6) were synthesized as reported earlier. Both of these compounds were converted into 2′-fluoro-2′-deoxy-3′-C-ethynyl and 3′-C-vinyl-β-D- lyxofuranosyl nucleosides (16-19) by a multistep sequence. All these new nucleosides were evaluated against seven human tumor cell lines in vitro. Copyright Taylor & Francis, Inc.

Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1)

A range of 2'-fluoro and 2',3'-difluoro analogues of pyrimidine deoxyribonucleosides have been synthesized and evaluaed against human immunodeficiency virus (HIV-1) in a human lymphoblastoid cell line. Among these compounds, 1-(2,3-dideoxy-2-fluoro-β-D-threopentofuranosyl)cytosine (12), 2',3'-didehydro-2',3'-dideoxy-2'-fluorocytidine (35), 1-(2,3-dideoxy-2,3-difluoro-β-D-arabinofuranosyl)cytosine (41), and 3'-deoxy-2',3'-didehydro-2'-fluorothymidine (45) were found to have significant antiviral activity, with IC50 values of 0.65, 10, 10, and 100 μM, respectively. The structure-activity relationships are discussed.

Antiviral Nucleosides. A Stereospecific, Total Synthesis of 2'-Fluoro-2'-deoxy-β-D-arabinofuranosyl Nucleosides

A general, total synthesis of (2'-fluoro-2'-deoxy-β-D-arabinofuranosyl)uracils 1a-d is described.A study of the coupling reaction beetwen 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide (7) and silylated pyrimidines 11a-d has resulted in a high overall yield for the five-step stereospecific synthesis of β-nucleosides.