5442-24-0

Basic information

• Product Name: 4-AMINO-2,6-DIHYDROXY-5-NITROSOPYRIMIDINE
• Synonyms: 4-AMINO-2,6-DIHYDROXY-5-NITROSOPYRIMIDINE;4-AMINO-5-NITRO-2,6-PYRIMIDINEDIOL;6-AMINO-2,4-DIHYDROXY-5-NITROSOPYRIMIDINE;6-AMINO-5-NITROSOURACIL;5-Nitroso-6-aminopyrimidine-2,4-diol;6-Amino-5-nitroso-2,4(1H,3H)-pyrimidinedione;2,4(1H,3H)-PyriMidinedione, 6-aMino-5-nitroso-;4-Amino-5-nitro-2,6-pyrimidinediol 6-Amino-5-nitrosouracil
• CAS NO: 5442-24-0
• Molecular Formula: C₄H₄N₄O₃
• Molecular Weight: 156.1
• EINECS: 226-633-4
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;API intermediates
• Mol File: 5442-24-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 119.2°C750mm Hg(lit.)
• Flash Point: 57°F
• Appearance: /
• Density: 0.806g/mLat 25°C(lit.)
• PKA: 0.56±0.10(Predicted)
• CAS DataBase Reference: 4-AMINO-2,6-DIHYDROXY-5-NITROSOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-2,6-DIHYDROXY-5-NITROSOPYRIMIDINE(5442-24-0)
• EPA Substance Registry System: 4-AMINO-2,6-DIHYDROXY-5-NITROSOPYRIMIDINE(5442-24-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1325
• WGK Germany: 3
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 5442-24-0(Hazardous Substances Data)

Usage

Uses

6-Amino-5-nitrosouracil is used in the preparation of palladium(II) complexes with 5-nitrosopyrimidines which display antiproliferative effects. Useful heterocyclic reagent in the synthesis of substituted purine derivatives displaying anti-thyroid activity.

InChI:InChI=1/C4H4N4O3/c5-2-1(8-11)3(9)7-4(10)6-2/h(H4,5,6,7,9,10)

Upstream product

• 873-83-6 4-Amino-2,6-dihydroxypyrimidine 
• 894-63-3 7-hydroxy-1,3-dimethyl-8-phenylxanthine 
• 105-56-6 ethyl 2-cyanoacetate 
• 57-13-6 urea 
• 61033-06-5 8-Propyl-7-hydroxyxanthine 
• 82161-01-1 7-Hydroxy-8-(4-nitro-phenyl)-3,7-dihydro-purine-2,6-dione 
• 82160-95-0 8-(p-Methoxyphenyl)-7-hydroxyxanthine 
• 82160-96-1 8-(p-Chlorophenyl)-7-hydroxyxanthine 
• 82160-94-9 8-Phenyl-7-hydroxyxanthine 

Downstream Products

• 82160-96-1 8-(p-Chlorophenyl)-7-hydroxyxanthine 
• 82160-94-9 8-Phenyl-7-hydroxyxanthine 
• 82160-95-0 8-(p-Methoxyphenyl)-7-hydroxyxanthine 
• 42965-55-9 5,6-diaminouracil sulfate 
• 33744-31-9 2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pteridine-6-carboxylic acid 
• 3240-72-0 5,6-diaminouracil 
• 69-89-6 xanthin 
• 5807-13-6 1,3,6,8-tetrahydro-2,4,5,7-pyrimido<5,4-g>pteridinetetrone 

Relevant articles and documents

Spectrophotometric investigation of 5-nitroso-6-aminouracil and its methyl derivative in methanol by selective complexation with bivalent metal ions

6-Amino-5-nitrosouracils are synthesized by the condensation reaction of urea or N,N′-dimethyl urea, cyanoacetic acid and acetic anhydride followed by nitrosation reaction with sodium nitrite. The synthesized compounds are characterized by various spectroscopic techniques like FTIR, NMR, single crystal XRD, and UV–vis absorption spectroscopy. From a single-crystal X-ray crystallography study of DANU, it is found that the compound is crystalline with one water molecule. The binding properties of both compounds with various metal ions are studied using UV–vis spectroscopy, where ANU shows a colour change from colourless to yellow colour-forming complex with cobalt metal ion. While DANU shows a colour change from colourless to dark yellow forming complex with copper and nickel cation, respectively. These compounds showed the job's plots with Cu2+, Ni2+, and Co2+ in various stoichiometric ratios to form the respective metal complex. The association/binding constant (Ka) values are calculated by plotting Benesi–Hilderbrand plots of ANU with Co2+ ion and is found to be 9.524 × 102. Whereas, DANU with Cu2+, Ni2+ are found to be 3.956 × 103, 2.041 × 103, respectively. These cations may be used in metal ions complexation for the respective ligand. The LOD values for ANU-Co2+, DANU-Cu2+ & DANU-Ni2+ are obtained as 33.9428 μM, 93.8082 μM and 48.396 μM, respectively, whereas the LOQ values are found as 102.857 μM, 284.2675 μM and 146.653 μM, respectively.

Synthesis and evaluation of antitumour activities of novel fused tri-And tetracyclic uracil derivatives

Simple one-pot syntheses of indenopyrrolopyrimidines and indolopyrrolopyrimidines were achieved via the cyclocondensation of 6-Aminouracils and, respectively, ninhydrin and isatin in the presence of catalytic amounts of glacial acetic acid. Similarly, 5,6-diaminouracil derivatives were used as starting materials for the synthesis of indenopteridines and indolopteridines via their reaction with ninhydrin and isatin, respectively. The synthesised compounds were evaluated for antitumour activity against a human hepatocellular carcinoma cell line (HepG2), some showing antitumour activity comparable with 5-fluorouracil and imatinib.

Synthesis of Paraxanthine Analogs (1,7-Disubstituted Xanthines) and Other Xanthines Unsubstituted at the 3-Position: Structure-Activity Relationships at Adenosine Receptors

Synthetic procedures for the preparation of various 3-unsubstituted xanthines, including paraxanthine analogs (1,7-disubstituted xanthines) and 1,8-disubstituted xanthines, were developed.Sylylation of 1-substituted xanthines followed by alkylation at the 7-position provides a facile route to paraxanthine analogs.Regioselective alkylation of tris(trimethylsilyl)-6-aminouracil provides 3-substituted 6-aminouracils, which are converted to 1,8-disubstituted xanthines by standard procedures.The ring closure of 3-substituted 5-cyclopentanecarboxamido- and 5-(benzoylamino)-6-aminouracils requires drastic reaction conditions.Affinity for brain A1 and A2 adenosine receptors was determined in binding assays for these and other xanthines with substituents in 1-, 3-, 7-, 8-, and 9-positions.Substitution at the 1-position was necessary for high affinity at adenosine receptors. 1,3-Disubstituted xanthines generally had higher affinity than 1,7-disubstituted xanthines. 1,8-Disubstituted xanthines had high affinity for adenosine receptors; some were highly selective for A1 receptors.