CAS 5442-24-0

6-Amino-5-nitroso-2,4(1H,3H)-pyrimidinedione

Description:

6-Amino-5-nitroso-2,4(1H,3H)-pyrimidinedione, with the CAS number 5442-24-0, is a heterocyclic organic compound characterized by its pyrimidine ring structure, which contains both amino and nitroso functional groups. This compound typically exhibits a pale yellow to orange color and is soluble in polar solvents, reflecting its polar nature due to the presence of amino and nitroso groups. It is known for its potential applications in medicinal chemistry, particularly as an intermediate in the synthesis of various pharmaceuticals. The presence of the nitroso group can impart unique reactivity, making it useful in organic synthesis. Additionally, the compound may exhibit biological activity, although specific biological properties would depend on the context of its use and the presence of other substituents. As with many nitrogen-containing heterocycles, it may also participate in hydrogen bonding, influencing its interactions in biological systems. Proper handling and safety measures should be observed due to the potential reactivity of nitroso compounds.

Formula: C₄H₄N₄O₃

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

InChI key: InChIKey=DKPCSXFEWFSECE-UHFFFAOYSA-N

SMILES: N(=O)C1=C(N)NC(=O)NC1=O

Synonyms:

• 2,4(1H,3H)-Pyrimidinedione, 6-amino-5-nitroso-
• 4-Amino-5-nitroso-2,6-pyrimidinediol
• 5-Nitroso-6-aminouracil
• 6-Amino-5-nitroso-2,4(1H,3H)-pyrimidinedione
• 6-Amino-5-nitroso-2,4-pyrimidinediol
• 6-Amino-5-nitroso-22,4(1H,3H)-pyrimidinedione
• 6-Amino-5-nitrosouracil
• NSC 11446
• NSC 14287
• NSC 3101
• NSC 677501
• NSC 94946

4-Amino-2,6-Dihydroxy-5-Nitrosopyrimidine

CAS: 5442-24-0

Formula: C₄H₄N₄O₃

Purity: >93.0%(HPLC)

Color and Shape: Solid

Molecular weight: 156.0996

Ref: IN-DA003KOE

6-Amino-5-nitroso-1,2,3,4-tetrahydropyrimidine-2,4-dione

CAS: 5442-24-0

6-Amino-5-nitroso-1,2,3,4-tetrahydropyrimidine-2,4-dione

Purity: ≥95%

Ref: 54-OR26563

6-Amino-5-nitrosouracil-13C2

Controlled Product

CAS: 5442-24-0

Applications Isotope labelled 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.
References Illan-Cabeza, N. et al.: J. Inorg. Biochem., 126, 118 (2013); Fatima, I. et al.: J. Mexi. Chem. Soc., 54, 227 (2010);

Formula: C₂C₂H₄N₄O₃

Color and Shape: Neat

Molecular weight: 158.085

Ref: TR-A618512

4-Amino-2,6-dihydroxy-5-nitrosopyrimidine

CAS: 5442-24-0

4-Amino-2,6-dihydroxy-5-nitrosopyrimidine is a molecule that has been shown to be an effective inhibitor of the enzyme tyrosinase in the oxidation of tyrosine to DOPA, which is a precursor of melanin. It is believed that vibrational and structural changes during these reactions are responsible for the inhibitory effects. 4-Amino-2,6-dihydroxy-5-nitrosopyrimidine has also been shown to have anti cancer effects on glioma cells. This molecule binds to copper ions, forming a chelate ring that can stabilize reactive intermediates and terminate free radicals. The chlorine atom on this molecule may be responsible for its cytotoxic effects by reacting with nucleophilic sites on proteins. The functional groups on this molecule react with acid catalysts, such as protonation or dehydration reactions.

Formula: C₄H₄N₄O₃

Purity: Min. 98 Area-%

Color and Shape: Powder

Molecular weight: 156.1 g/mol

Ref: 3D-NA70257

4-AMINO-2,6-DIHYDROXY-5-NITROSOPYRIMIDINE

CAS: 5442-24-0

Formula: C₄H₄N₄O₃

Purity: 95.0%

Molecular weight: 156.101

Ref: 10-F513577

6-Amino-5-nitrosouracil-13C,15N2

Controlled Product

CAS: 5442-24-0

Applications 6-Amino-5-nitrosouracil-13C,15N2 is an intermediate in the synthesis of Xanthine-13C15N2 (X499952), which is an isotope labelled analog of Xanthine (X499950), a substance that can be found in animal organs, yeast, potatoes, coffee beans, tea. Xanthine can be used to relax and widen certain breathing passages of the lungs. It is also found that a large number of derivatives that exhibits adenoside receptor antagonist properties.
References Mueller, C. et. al: Handbook Exp. Pharmacol. 200,151(2011)

Formula: CC₃H₄₁₅N₂N₂O₃

Color and Shape: Neat

Molecular weight: 159.079

Ref: TR-A618511

4-Amino-2,6-dihydroxy-5-nitrosopyrimidine

CAS: 5442-24-0

Formula: C₄H₄N₄O₃

Purity: >93.0%(HPLC)

Color and Shape: Red to Purple powder to crystal

Molecular weight: 156.10

Ref: 3B-A1202