42965-55-9

Usage

InChI:InChI=1/C4H6N4O2.H2O4S/c5-1-2(6)7-4(10)8-3(1)9;1-5(2,3)4/h5H2,(H4,6,7,8,9,10);(H2,1,2,3,4)/p-2

Upstream product

• 5442-24-0 6-amino-5-nitrosouracil 

Downstream Products

• 5807-13-6 1,3,6,8-tetrahydro-2,4,5,7-pyrimido<5,4-g>pteridinetetrone 
• 1468-26-4 8-azaxanthine 
• 13401-38-2 7-methyl-1H-pteridine-2,4-dione 
• 69-89-6 xanthine 
• 13401-38-2 7-methyl-pteridine-2,4-diol 
• 5768-84-3 phenanthro[9,10-g]pteridine-11,13(10H,12H)-dione 
• 14892-98-9 6,7-diphenylpteridine-2,4(1H,3H)-dione 
• 109187-20-4 6-vanillyl-1H,8H-pteridine-2,4,7-trione 
• 50996-21-9 7-phenyl-2,4(1H,3H)-pteridinedione 
• 50996-22-0 6-phenyl-lumazine 
• 2577-35-7 5,6-Dihydro-6-oxolumazin 
• 487-21-8 pteridine-2,4-(1H,3H)-dione 
• 5774-32-3 2,4-Dihydroxy-6,7-dimethyl-pteridin 
• 1213789-30-0 3-(2-aminophenyl)-6,8-dihydroxypyrazino[5,6-b]pyrimidine 

Relevant academic research and scientific papers

Synthesis of purine antiviral agents, hypoxanthine and 6-mercaptopurine

Some potentially biologically active 6-substituted purine derivatives have been synthesized from simple organic reagents. The reaction of urea with ethyl cyanoacetate gave 6-aminopyrimidine-2,4-dione which was converted in two steps into purine derivative, xanthine. The latter was treated with formamide at 200°C to obtain hypoxanthine. The chlorination of hypoxanthine with POCl3 gave 6-chloropurine which was converted into 6-mercaptopurine via reaction with thiourea in acetonitrile, followed by treatment with boiling ethanol.

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.