131-06-6

Usage

Uses

Used in Oncology:
1-beta-D-arabinofuranosyl-5-fluoro-(1H,3H)-pyrimidine-2,4-dione is used as an antineoplastic agent for the treatment of chronic lymphocytic leukemia (CLL) and non-Hodgkin's lymphoma. It is effective in inhibiting the growth and proliferation of cancer cells by disrupting DNA and RNA synthesis, leading to cell death.
Used in Hematologic Malignancies:
In the field of hematology, 1-beta-D-arabinofuranosyl-5-fluoro-(1H,3H)-pyrimidine-2,4-dione is used as a therapeutic agent for various hematologic malignancies. Its ability to target rapidly dividing cells makes it a valuable tool in the management of these conditions.
Used in Immunosuppression:
Due to its immunosuppressive properties, 1-beta-D-arabinofuranosyl-5-fluoro-(1H,3H)-pyrimidine-2,4-dione is used in situations where the immune system needs to be suppressed, such as in the treatment of autoimmune diseases or in organ transplantation to prevent rejection.

InChI:InChI=1/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6+,8-/m1/s1

Upstream product

• 3083-77-0 araU 
• 78948-09-1 acetyl hypofluorite 
• 316-46-1 5-fluorouridine 
• 119003-30-4 Acetic acid (4R,5S)-3-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoro-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 119003-30-4 Acetic acid (4S,5R)-3-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-fluoro-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 17242-86-3 5-fluoro-1-(tri-O-benzoyl-β-D-arabinofuranosyl)-1H-pyrimidine-2,4-dione 
• 6160-61-8 5-fluoro-2',3',5'-tri-O-acetyl arabinosyl uridine 
• 4348-69-0 1-(tri-O-benzoyl-β-D-arabinofuranosyl)-1H-pyrimidine-2,4-dione 
• 17242-86-3 1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-5-fluorouracil 
• 4348-69-0 C₃₀H₂₄N₂O₉ 
• 77180-90-6 1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-fluorouracil 
• 446251-78-1 1-(3'-O-benzyl-β-L-ribofuranosyl)-5-fluorouracil 
• 849342-81-0 C₂₅H₂₁FN₂O₉ 
• 171721-12-3 1,2-di-O-isopropylidene-3,5-di-O-benzoyl-α-L-ribofuranose 

Relevant academic research and scientific papers

Syntheses of 5-fluoro and (E)-5-(2-fluorovinyl) arabinosyl uridine analogues as potential probes for the HSV-1 thymidine kinase gene

The syntheses of 5-fluoro (FaraU) and (E)-5-(2-fluorovinyl) arabinosyl uridine (FVAU) via 5-trimethylstannyl and (E)-5-(2-tributylstannylvinyl) arabinosyl uridine analogues with select-fluor is described. Boc protection of the uridine moiety improved the yield of synthesis and differences between N-Boc and O-Boc isomers were established by 1H- and 13C NMR. The Boc-protected stannyl intermediates may be fluorinated with 18F to produce [18F]FaraU and [18F]FVAU. Georg Thieme Verlag Stuttgart.

Synthesis of O2,2′-cyclo-β-D-arabinofuranosyl- and β-D-arabinofuranosyl-5-fluorocytosine

Methods for the synthesis of 5-fluorocytosine by direct fluorination of cytidine tetraacetate with elementary fluorine in acetic acid and by amination of 5-fluorouridine triacetate by the action of sodium hydride and p-toluenesulfonyl chloride and subsequent ammonolysis were studied. 5-Fluorocytidine was converted to O2, 2′-cyclo-β-D-arabinofuranosyl-5-fluorocytosine by the successive action of acetylsalicylyl chloride and acetyl chloride in methanol to remove the protective groups. Removal of the protective groups by means of a methanol solution of ammonia gave β-D-arabinofuranosyl-5-fluorocytosine. The latter was also obtained by amination of β-D-arabinofuranosyl-5-fluorouracil tribenzoate.

THERMOSTABLE BIOCATALYST COMBINATION FOR NUCLEOSIDE SYNTHESIS

The present invention relates to a transglycosylation method for the preparation of natural and synthetic nucleosides using a uridine phosphorylase (PyNPase, E.C. 2.4.2.3), a purine nucleoside phosphorylase (PNPase, E.C. 2.4.2.1), or a combination thereof. These biocatalysts may be used as such, or by means of host cells transformed with vectors comprising recombinant DNA gene derived from hyperthermophilic archaea and encoding for the PyNPase and PNPase enzymes.

Synthesis and anti-viral activity of a series of D- and l-2′-deoxy-2′-fluororibonucleosides in the subgenomic HCV replicon system

Based on the discovery of (2′R)-D-2′-deoxy-2′- fluorocytidine as a potent anti-hepatitis C virus (HCV) agent, a series of D- and L-2′-deoxy-2′-fluororibonucleosides with modifications at 5- and/or 4-positions were synthesized and evaluated for their in vitro activity against HCV and bovine viral diarrhea virus (BVDV). The key step in the synthesis, the introduction of 2′-fluoro group, was achieved by either fluorination of 2,2′-anhydronucleosides with hydrogen fluoride-pyridine or potassium fluoride, or a fluorination of arabinonucleosides with DAST. Among the 27 analogues synthesized, only the 5-fluoro compound, namely (2′R)-D-2′-deoxy-2′,5-difluorocytidine (13), demonstrated potent anti-HCV activity and toxicity to ribosomal RNA. The replacement of the 4-amino group with a thiol group resulted in the loss of activity, while the 4-methylthio substituted analogue (25) exhibited inhibition of ribosomal RNA. As N4-hydroxycytidine (NHC) had previously shown potent anti-HCV activity, we combined the two functionalities of the N4-hydroxyl and the 2′-fluoro into one molecule, resulting (2′R)-D-2′-deoxy- 2′-fluoro-N4-hydroxycytidine (23). However, this nucleoside showed neither anti-HCV activity nor toxicity. All the L-forms of the analogues were devoid of anti-HCV activity. None of the compounds showed anti-BVDV activity, suggesting that the BVDV system cannot always predict anti-HCV activity.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides

Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramolecular SN2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbrüggen's conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.

Stereospecific synthesis and biological evaluations of β-L-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine

In the search for new chemotherapeutic agents, we have focused our work on the synthesis and the study of several unnatural β-L-nucleoside analogues. In this paper, we report on the synthesis of β-L-pentofuranonucleosides (and their 2′-deoxy derivatives) of 5-fluorouracil and their inhibitory effects on the proliferation of several murine and human tumor cells. The corresponding 5-fluorocytosine derivatives were also synthesized and their anti-HIV and anti-HBV activities have been evaluated.

A stereospecific synthesis of L-ribose and L-ribosides from D-galactose

An inexpensive D-galactose was converted into L-ribose and its derivatives via mild reaction conditions. The L-ribosyl donor was submitted to a glycosidation according to Vorbrüggen's conditions to give L-ribosides in high yields.

L-ribofuranosyl nucleosides

This invention relates to α and β L-ribofuranosyl nucleosides, processes for their preparation, pharmaceutical compositions containing them, and methods of using them to treat various diseases in mammals.

Reaction of Acetyl Hypofluorite with Pyrimidines. Part 3. Synthesis, Stereochemistry, and Properties of 5-Fluoro-5,6-dihydropyrimidine Nucleosides

The reaction of acetyl hypofluorite (AcOF) with unprotected uracil and cytosine nucleosides in acetic acid or water has been studied using (18)F as a tracer.For the nucleosides in general two cis-diastereoisomers of both the 6-acetoxy-5-fluoro and 5-fluoro-6-hydroxy adducts were obtained, (1)H n.m.r. analysis of which showed that they all possessed the anti-conformation.The 6-acetoxy-5-fluoroadducts in the uracil nucleosides showed a remarkable stability and appeared to be interesting versatile compounds.They could be converted into their hitherto unknown corresponding 5-fluoro-6-hydroxy-O6,5'-anhydrocyclouracil nucleosides.For the cytosine nucleosides the 6-acetoxy-5-fluoro adducts were not observed, while the other cytosine adducts were found to rapidly deaminate at C-4 in water yielding the corresponding uracil analogues.Interestingly, even within a pair of diastereoisomers different deamination rates were observed.