97614-47-6

Usage

Uses

Used in Oncology:
2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylis used as an anticancer agent for the treatment of various malignancies, particularly chronic lymphocytic leukemia. Its benzoyl and fluoro modifications make it more potent in inhibiting DNA synthesis and repair, thereby disrupting the growth and spread of cancer cells.
Used in Pharmaceutical Development:
2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylis utilized in the development of new cancer therapies, as its unique structure and properties offer potential for improved efficacy and selectivity in targeting cancer cells. Its intravenous administration allows for direct delivery to the site of the tumor, enhancing its therapeutic effects.
Used in Research:
2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methylserves as a valuable research tool in studying the mechanisms of action of nucleoside analogs in cancer treatment. Its modified structure provides insights into the role of benzoyl and fluoro groups in enhancing the compound's potency and effectiveness.
Used in Drug Resistance Studies:
2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-'s ability to target cancer cells effectively makes it a candidate for studying drug resistance in cancer treatment. Its use in combination with other chemotherapeutic agents can help explore synergistic effects and potential strategies to overcome drug resistance in cancer cells.

Upstream product

• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 97614-42-1 2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 65-71-4 thymin 

Downstream Products

• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 
• 1383974-91-1 (5S,6R)-1-[(2R,3S,4R,5R)]-3',5'-di-O-trityl-5,6-dihydroxy-2'-arabinofluorothymidine 
• 1383974-97-7 (5R,6S)-1-[(2R,3S,4R,5R)]-3',5'-di-O-trityl-5,6-dihydroxy-2'-arabinofluorothymidine 
• 97672-34-9 1-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)thymine 
• 163252-36-6 1-(2'-fluoro-2'-deoxy-α/β-D-arabinofuranosyl)thymine 
• 144822-48-0 5′-O-(dimethoxytrityl)-2′-β-fluorothymidine 

Relevant academic research and scientific papers

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.

Probing Synergistic Effects of DNA Methylation and 2′-β-Fluorination on i-Motif Stability

The possible role of DNA i-motif structures in telomere biology and in the transcriptional regulation of oncogene promoter regions is supported by several recent studies. Herein we investigate the effect of four cytidine nucleosides (and combinations thereof) on i-motif structure and stability, namely 2′-deoxycytidine (dC), 2′-deoxy-5-methyl-cytidine (5-Me-dC), 2′-deoxy-2′-fluoro-arabinocytidine (2′F-araC), and 2′-deoxy-2′-fluoro-5-methyl-arabinocytidine (5-Me-2′F-araC). The base pair 5-Me-2′F-araC:2′F-araC produced i-motifs with a pH1/2 (“pKa”) value that closely matches physiological pH (7.34±0.3). NMR analysis of the most stable telomeric sequence (HJ-2) at pH 7.0 indicated that the structure is stabilized by hybrid 5-Me-dC:2′F-araC hemiprotonated base pairs and therefore highlights the significance of the interplay between base and sugar modifications on the stability of i-motif structures.

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 2′-deoxy-2′-fluoro-1-β-D-arabinofuranosyl uracil derivatives: A method suitable for preparation of [18F]-labeled nucleosides

N-glycosylation of 2,4-bis-O-(trimethylsilyl)-pyrimidine bases with 2-deoxy-2-fluoro-3,5-di-O-benzoyl-l-(Br, OBz)-α-D-arabinose derivatives are reported. 1-Bromo-arabinose provides high yield and a favorable anomeric ratio (β/α) of pyrimidine nucleoside i

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.