30868-30-5

Usage

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-3-BETA-D-RIBOFURANOSYL-1H-PYRAZOLE-5-CARBOXAMIDE MONOHYDRATE is used as a pharmaceutical compound for its potential therapeutic properties. 4-HYDROXY-3-BETA-D-RIBOFURANOSYL-1H-PYRAZOLE-5-CARBOXAMIDE MONOHYDRATE's unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Anticancer Applications:
In the field of oncology, 4-HYDROXY-3-BETA-D-RIBOFURANOSYL-1H-PYRAZOLE-5-CARBOXAMIDE MONOHYDRATE is used as an anticancer agent. Its chemical structure enables it to modulate various oncological signaling pathways, potentially leading to the inhibition of tumor growth and progression. Furthermore, it may demonstrate synergistic effects when combined with conventional chemotherapeutic drugs, enhancing their efficacy and overcoming resistance in certain cases.
Used in Drug Delivery Systems:
To improve the bioavailability and therapeutic outcomes of 4-HYDROXY-3-BETA-D-RIBOFURANOSYL-1H-PYRAZOLE-5-CARBOXAMIDE MONOHYDRATE, it is used in the development of novel drug delivery systems. These systems, which may include organic and metallic nanoparticles, serve as carriers for the compound, enhancing its delivery to target cells and tissues, and potentially improving its overall efficacy in treating various conditions, including cancer.

Biochem/physiol Actions

Pyrazofurin serves as an effective drug against HIV (human immuno virus), vaccinia virus, West Nile viral infection.

Enzyme inhibitor

This pyrimidine nucleoside (FW = 261.23 g/mol), also known as pyrazomycin, exhibits antineoplastic activity and inhibits cell proliferation and DNA synthesis in cells by inhibiting orotidylate decarboxylase (uridine 5'-phosphate synthase). Pyrazofurin, also known as 3,b-D-ribofuranosyl-4- hydroxypyrazole-5-carboxamide, is the prodrug of the 5’-phosphate derivative. Target(s): adenosylhomocysteinase; 5-aminoimidazole-4- carboxamide-1-b-D-ribofuranosyl 5'-monophosphate formyltransferase; orotate phosphoribosyltransferase; orotidylate decarboxylase, or UMP synthase.

InChI:InChI=1/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5-,7-,8+/m1/s1

Upstream product

• 79264-07-6 2',3',5'-tri-O-acetylpyrazofurin 
• 59252-17-4 2′,3′-O-isopropylidenepyrazofurin 
• 83686-32-2 ethyl 4-hydroxy-3-(2′,3′-O-isopropylidene-5′-O-trityl-β-D-ribofuranosyl)pyrazole-5-carboxylate 
• 57274-20-1 2-[O²,O³-isopropylidene-O⁵-(4-nitro-benzoyl)-α-D-ribofuranosyl]-3-oxo-pentanedioic acid diethyl ester 
• 57274-23-4 5-[O²,O³-isopropylidene-O⁵-(4-nitro-benzoyl)-α-D-ribofuranosyl]-4-oxo-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid diethyl ester 
• 57274-24-5 4-hydroxy-5-(O²,O³-isopropylidene-α-D-ribofuranosyl)-1(2)H-pyrazole-3-carboxylic acid ethyl ester 
• 102803-76-9 methyl 2-diazo-4-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-3-oxobutanoate 
• 102803-75-8 methyl 2-diazo-4-(2,3-O-isopropylidene-5-O-trityl-α-D-ribofuranosyl)-3-oxobutanoate 
• 102803-71-4 4-((3aS,6R,6aR)-2,2-Dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-oxo-butyric acid methyl ester 
• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 59252-17-4 4-hydroxy-5-(O²,O³-isopropylidene-α-D-ribofuranosyl)-1(2)H-pyrazole-3-carboxylic acid amide 
• 83686-33-3 4-hydroxy-3-(2′,3′-O-isopropylidene-5′-O-trityl-β-D-ribofuranosyl)pyrazole-5-carboxamide 
• 83686-35-5 4-hydroxy-3-(2',3'-O-isopropylidene-5'-O-trityl-α-D-ribofuranosyl)pyrazole-5-carboxamide 
• 37116-66-8 2-benzyl-4-hydroxy-5-β-D-ribofuranosyl-2H-pyrazole-3-carboxylic acid methyl ester 

Downstream Products

• 99298-13-2 4-(benzyloxy)-3β-ribofuranosylpyrazole-5-carboxamide 
• 133470-83-4 2,4-O-dibenzylpyrazofurin 
• 133470-82-3 1,4-O-dibenzylpyrazofurin 
• 133470-87-8 1,4-O-dibenzyl-2',3',5'-tri-O-acetylpyrazofurin 
• 133470-84-5 1-benzyl-4,2',3',5'-tetra-O-acetylpyrazofurin 
• 133470-89-0 1-benzyl-5-(methylthio)-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo<3,4-e><1,3>oxazin-7-one 
• 133470-88-9 1-benzyl-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo<3,4-e><1,3>oxazine-5,7-dione 
• 133470-85-6 1,benzyl-2',3',5'-tri-O-acetylpyrazofurin 
• 133471-02-0 Acetic acid (2R,3S,4R,5S)-5-(5-amino-1-benzyl-7-oxo-1,7-dihydro-pyrazolo[3,4-e][1,3]oxazin-3-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 
• 133470-90-3 5-amino-1-benzyl-3-β-D-ribofuranosylpyrazolo<3,4-e><1,3>oxazin-7-one 
• 90524-84-8 3-β-D-ribofuranosylpyrazolo<3,4-e><1,3>oxazine-5,7-dione 
• 37085-15-7 1-benzylpyrazofurin 
• 99298-33-6 4-(benzyloxy)-5-carbamoyl-3-β-ribofuranosylpyrazolyl(5->5')adenosine pyrophosphate 
• 99298-24-5 Acetic acid (2S,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-benzyloxy-5-thiocarbamoyl-1H-pyrazol-3-yl)-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

A New Synthsis of Pyrazofurin

Pyrazofurin (4) has been synthesised by a novel route, involving, as the key step, photochemical substitution of a diazopyrazole.

The first chemical synthesis of pyrazofurin 5′-triphosphate

As an archetype C-nucleoside, pyrazofurin possesses broad-spectrum antiviral and antitumor activities. However, the presence of the acidic enol in the nucleobase of pyrazofurin poses a huge challenge to the conventional NTP synthetic methods. On the basis

SYNTHESIS OF PYRAZOFURINS: FURTHER CORRELATIONS BETWEEN CONFIGURATION-CONFORMATION AND (1)H-N.M.R. DATA FOR C-(2,3-O-ISOPROPYLIDENEGLYCOFURANOSYL) DERIVATIVES

Methyl 4-(2,3-O-isopropylidene-5-O-trityl-α- and -β-D-ribofuranosyl)-3-oxobutanoate (5α and 5β) were prepared in good yield by reacting 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose with 3-methoxycarbonylacetonylidenetriphenylphosphorane catalysed by ben

Synthesis of Pyrazofurin and its Analogues

Pyrazofurin and its analogues have been synthesized fron ribosyl β-keto acid derivatives, which can be readily prepared by Wittig reaction of the protected D-ribose with phosphoranes.Reaction of 2,3-O-isopropylidene-5-O-trityl-α- and β-D-ribose (6) with 3

A Simple Synthesis of the Pyrazofurins

Pyrazofurin (1) and pyrazofurin B (2) have been synthesised from the β-keto ester (5), which can be readily prepared by Wittig reaction of the protected D-ribose (3) with the phosphorane (4).

C-Nucleoside Studies. Part 14. A New Synthesis of Pyrazofurin

Treatment of 3-cyano-4-nitro-5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazole (4) with benzyl bromide and triethylamine gave as major product the 1-benzyl-5-cyano-isomer (5), whilst similar treatment of 5-cyano-3-methyl-4-nitropyrazole (7) gave exclusively 1-benzyl-3-cyano-5-methyl-4-nitropyrazole (8).This was converted into 4-amino-1-benzyl-3-carboxamido-5-methylpyrazole (10); attempts to convert (10) into a 4-hydroxypyrazole via the diazonium salt were unsuccessful, but photolysis of the diazonium salt (11) in aqueous trifluoroacetic acid-dioxan gave 1-benzyl-3-carboxamido-5-methylpyrazole (13) in 67percent yield.Treatment of 4-amino-3-cyano-5-methylpyrazole (14) with nitrous acid and subsequent neutralisation gave a diazopyrazole which on photolysis in aqueous acetone yielded 3-cyano-4-hydroxy-5-methylpyrazole (16) in 79percent overall yield.Application of the same sequence to 4-amino-3-cyano-5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-pyrazole (2) gave the 4-hydroxy-compound (17) (87percent overall), which was converted in two steps into pyrazofurin (1).