2465-59-0

Basic information

• Product Name: 4,6-DIHYDROXYPYRAZOLO[3,4-D]PYRIMIDINE
• Synonyms: 4,6-Dihydroxy-1H-pyrazolo[3,4-d]pyrimidine, 98+%;4,6-Dihydropyrazolo Pyrimidine;4,6-Dihydroxypyrazolo[3,4-d]pyrimidine,99%;4,6-Dihydroxypyrazolo[3,4-d]pyrimidine ,96%;4,6-Dihydroxy-1H-pyrazolo[3,4-d]pyrimidine;4,6-Dioxopyrazolo[3,4-d]pyrimidine;Oxyprim;4,6-Dihydroxypyrazolo[3,4-d]pyriMidine, 99% 5GR
• CAS NO: 2465-59-0
• Molecular Formula: C₅H₄N₄O₂
• Molecular Weight: 152.11
• EINECS: 219-570-9
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Heterocycles, Metabolites & Impurities, Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals;Pyridines, Pyrimidines, Purines and Pteredines;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 2465-59-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 274.55°C (rough estimate)
• Flash Point: 354.7 °C
• Appearance: Light yellow/Powder
• Density: 1.637
• Vapor Pressure: 3.5E-18mmHg at 25°C
• Refractive Index: 1.8500 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in DMSO.
• PKA: pKa 7.7 (Uncertain)
• Stability: Hygroscoipic
• BRN: 139956
• CAS DataBase Reference: 4,6-DIHYDROXYPYRAZOLO[3,4-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIHYDROXYPYRAZOLO[3,4-D]PYRIMIDINE(2465-59-0)
• EPA Substance Registry System: 4,6-DIHYDROXYPYRAZOLO[3,4-D]PYRIMIDINE(2465-59-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2465-59-0(Hazardous Substances Data)

Usage

Chemical Properties

Off White Solid

Uses

Different sources of media describe the Uses of 2465-59-0 differently. You can refer to the following data:
1. A metabolite of Allopurinol.
2. 4,6-Dihydroxy-1H-pyrazolo[3,4-d]pyrimidine is an inhibitor to study the specificity and kinetics of xanthine oxidase. It is also used as an anti-inflammatory agent via inhibition of xanthine oxidase.
3. Oxypurinol, an allopurinol metabolite, is used as an inhibitor to study the specificity and kinetics of of xanthine oxidase(s). Oxypurinol is also used as an anti-inflammatory agent via inhibition of xanthine oxidase.

Definition

ChEBI: A pyrazolopyrimidine that is 4,5,6,7-tetrahydro-H-pyrazolo[3,4-d]pyrimidine substituted by oxo groups at positions 4 and 6.

Biological Activity

oxipurinol is a xanthine oxidoreductase inhibitor.xanthine oxidoreductase (xo), a complex molybdoflavoenzyme present in milk and many other tissues, has been studied for many years. xo is generally recognized as a critical enzyme in purine catabolism.

Biochem/physiol Actions

An allopurinol metabolite.

in vitro

allopurinol could be rapidly oxidized by xo to its active metabolite oxypurinol (both isosteres of hypoxanthine and xanthine, respectively), which also could inhibit xo. oxypurinol was identified as a noncompetitive inhibitor of xo; the formation of this compound was reported to be responsible for much of the pharmacological activity of allopurinol. moreover, both allopurinol and oxypurinol showed free radical scavenging effects in isolated hearts, and exerted cardioprotective effects despite no detectable xo activities [1].

in vivo

animal study found that in the vasculature of hypercholesterolemic rabbits, oxypurinol treatment led to a decrease in vascular free radical production [1].

references

[1] p. pacher, a. nivorozhkin and c. szabó. therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. pharmacological reviews 58(1), 87-114 (2006).[2] day ro, graham gg, hicks m, mclachlan aj, stocker sl, williams km. clinical pharmacokinetics and pharmacodynamics of allopurinol and oxypurinol. clin pharmacokinet. 2007;46(8):623-44.

InChI:InChI=1/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)

Upstream product

• 27511-79-1 3-amino-4-pyrazolocarboxamide hemisulfate 
• 57-13-6 urea 
• 98277-30-6 4,6-dimethoxy-1H-pyrazolo[3,4-d]pyrimidine 
• 315-30-0 4-hydroxypyrazolo(3,4-d)pyrimidine 
• 1336-21-6 ammonium hydroxide 
• 35344-99-1 3,4-pyrazole dicarboxylic acid 
• 21272-56-0 1⁽²⁾H-pyrazole-3,4-dicarboxylic acid diamide 
• 75-65-0 tert-butyl alcohol 
• 5334-31-6 5-amino-1H-pyrazole-4-carboxylic acid amide 
• 24521-76-4 6-thioxo-1,5,6,7-tetrahydropyrazolo<3,4-d>pyrimidin-4-one 
• 50270-27-4 2,4,6-trichloropyrimidine-5-carbaldehyde 
• 134221-52-6 4-chloro-2,6-dimethoxypyrimidine-5-carboxaldehyde 
• 246855-09-4 N-benzylidene-N'-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-hydrazine 
• 246855-07-2 6-Chloro-4-hydrazino-1H-pyrazolo[3,4-d]pyrimidine 

Downstream Products

• 139004-10-7 2-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<3,4-d>pyrimidine-4,6(5H,7H)-dione 
• 139004-08-3 7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrazolo<3,4-d>pyrimidine-4,6(1H,5H)-dione 
• 5334-33-8 4,5-Dihydro-4-thioxo-1H-pyrazolo[3,4-d]pyrimidin-6(7H)-one 
• 5334-32-7 1⁽²⁾,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dithione 
• 1037479-62-1 4,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1Hpyrazolo [3 ,4-d]pyrimidine 
• 1254783-78-2 N-(3-((6-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)phenyl)acrylamide 
• 1313036-50-8 6-chloro-4-(3-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1313036-52-0 N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-4-(3-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1313036-53-1 4-(3-aminophenoxy)-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1313036-54-2 N-(3-((6-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)phenyl)acrylamide 
• 42754-96-1 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine 
• 23771-52-0 4-amino-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-6-thione 
• 5472-41-3 4-amino-1,7-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 139004-04-9 7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-6-oxopyrazolo<3,4-d>pyrimidine-4(1H,5H)-thione 

Relevant articles and documents

Control of xanthine oxidase activity by light

Turning the light on and off can control the activity of xanthine oxidase (XOD) when allopurinol (1) is the substrate. Alloxanthin (2) is formed in the reaction but also acts as an inhibitor of the enzyme. Irradiation can free the active site and let the enzyme get on with its job. The alloxanthin - XOD system might have important future applications as a photoswitch/integrator in molecular-scale optobioelectronic devices.

FYX-051: A novel and potent hybrid-type inhibitor of xanthine oxidoreductase

4-[5-(Pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile (FYX-051) is a potent inhibitor of bovine milk xanthine oxidoreductase (XOR). Steady-state kinetics study showed that it initially behaved as a competitive-type inhibitor with a Ki value of 5.7 × 10 -9 M, then after a few minutes it formed a tight complex with XOR via a Mo-oxygen-carbon atom covalent linkage, as reported previously (Proc Natl Acad Sci USA 101:7931-7936, 2004). Thus, FYX-051 is a hybrid-type inhibitor exhibiting both structure- and mechanism-based inhibition. The FYX-051-XOR complex decomposed with a half-life of 20.4 h, but the enzyme activity did not fully recover. This was found to be caused by XOR-mediated conversion of FYX-051 to 4-[5-(2-hydroxypyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile (2-hydroxy-FYX-051), as well as formation of 6-hydroxy-4-[5-(2-hydroxypyridin-4- yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile (dihydroxy-FYX-051) and 4-[5-(2,6-dihydroxypyridin-4-yl)-1H-1,2,4-triazol-3-yl]-6-hydroxypyridine-2- carbonitrile (trihydroxy-FYX-051) during prolonged incubation for up to 72 h. A distinct charge-transfer band was observed concomitantly with the formation of the trihydroxy-FYX-051-XOR complex. Crystallographic analysis of the charge-transfer complex indicated that a Mo-nitrogen-carbon bond was formed between molybdenum of XOR and the nitrile group of trihydroxy-FYX-051. FYX-051 showed a potent and long-lasting hypouricemic effect in a rat model of potassium oxonate-induced hyperuricemia, and it seems to be a promising candidate for the clinical treatment of hyperuricemia. Copyright

Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine

A novel route for the synthesis of 4,5-difunctionalized uracils using a chemo- and regioselective bromine/magnesium exchange reaction on 5-bromo-4-halogeno-2,6-dimethoxypyrimidines has been developed. Applications to the synthesis of pharmaceuticals such as oxypurinol and emivirine are reported.

Novel xanthine oxidase inhibitor studies. Part 3. Convenient and general syntheses of 3-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-5(6H)-ones as a new class of potential xanthine oxidase inhibitors

Convenient and general syntheses of 3-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-5(6H)-ones (12), a new class of potent xanthine oxidase inhibitors, involving the oxidative cyclisation of 6-substituted 4-alkylidenehydrazino- or 4-arylmethylidenehydrazino-1H-pyrazolo[3,4-d]pyrimidines (3 and 11) with 70% nitric acid as the key step, are reported. The hydrazones 3 and 11 were obtained by a versatile synthetic route via the key intermediates, 6-chloro-4-hydrazino-1H-pyrazolo[3,4-d]pyrimidine 2 or oxypurinol 4, starting from 2,4,6-trichloropyrimidine-5-carbaldehyde 1. Their inhibitory activities against bovine milk xanthine oxidase in vitro are also described; i.e. the pyrazolotriazolopyrimidines 12 were several hundred times more potent than allopurinol.