52253-30-2

Upstream product

• 88-10-8 N,N-diethylcarbamyl chloride 
• 7803-49-8 hydroxylamine 
• 141-78-6 ethyl acetate 
• 872727-95-2 C₁₂H₁₈N₂O₂ 

Downstream Products

• 52253-36-8 1,1-Diethyl-5-phenyl-3-hydroxybiuret 
• 52253-49-3 1.1-Diaethyl-3-(4-chlorbenzoyloxy)-harnstoff 
• 52253-51-7 1.1-Diaethyl-3-(4-nitrobenzoyloxy)-harnstoff 
• 52253-37-9 C₁₂H₂₃N₃O₃ 
• 52253-47-1 C₁₂H₁₆N₂O₃ 

Relevant academic research and scientific papers

Hydroxyurea analogues as kinetic and mechanistic probes of the nitric oxide producing reactions of hydroxyurea and oxyhemoglobin

Derivatives of N-hydroxyurea that contain an N-hydroxy group react with oxyhemoglobin to form methemoglobin and variable amounts of nitrite/nitrate. Compounds with an unsubstituted -NHOH group produce the most nitrite/nitrate, which provides evidence for nitric oxide formation. The rate of reaction of these N-hydroxyurea derivatives with oxyhemoglobin correlates well with that compound's oxidation potential. Aromatic N-hydroxyureas react 25-80-fold faster with oxyhemoglobin than with N-hydroxyurea, suggesting other N-hydroxyurea analogues may be superior nitric oxide donors. Electron paramagnetic resonance spectroscopy shows that the formation of a low-spin methemoglobin - hydroxyurea complex is critical for iron nitrosyl hemoglobin formation. These results show that iron nitrosyl hemoglobin formation from the reaction of hydroxyureas and hemoglobin requires an unsubstituted -NHOH group and that the nitrogen atom of the non-N-hydroxy group must contain at least a single hydrogen atom. These results should guide the development of new hydroxyurea-based nitric oxide donors and sickle cell disease therapies.

A convenient method for the synthesis of N-hydroxyureas

Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In add