97614-47-6

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-;1-(3,5-Di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-Methyl-2,4(1H,3H)-pyriMidinedione;3',5'-Di-O-benzoyl-2'-deoxy-2'-fluoro-5-Methyl-beta-D-arabinouridine;1-(3,5-Di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
• CAS NO: 97614-47-6
• Molecular Formula: C₂₄H₂₁FN₂O₇
• Molecular Weight: 468.4311432
• Mol File: 97614-47-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-(97614-47-6)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-(97614-47-6)

Safety Data

• Hazardous Substances Data: 97614-47-6(Hazardous Substances Data)

Usage

General Description

2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl- is a chemical compound that is derived from the nucleoside analog fludarabine, which is used in the treatment of certain types of cancer, such as chronic lymphocytic leukemia. It is a potent inhibitor of DNA synthesis and repair, and it works by interfering with the growth and spread of cancer cells in the body. The compound is a modified form of fludarabine, with added benzoyl and fluoro groups, which make it more potent and effective in targeting cancer cells. It is commonly administered intravenously and has shown promising results in the treatment of various malignancies.

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 
• 65-71-4 thymin 
• 97614-42-1 2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 

Downstream Products

• 163252-36-6 1-(2'-fluoro-2'-deoxy-α/β-D-arabinofuranosyl)thymine 
• 144822-48-0 5′-O-(dimethoxytrityl)-2′-β-fluorothymidine 
• 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 
• 69256-17-3 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine 

Relevant articles and documents

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.

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.

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.