85102-47-2

Upstream product

• 100-39-0 benzyl bromide 
• 85102-51-8 1,3-dimethyl-5-nitro-6-phenethyluracil 
• 104-82-5 4-Methylbenzyl chloride 
• 59119-42-5 1,3-dimethyl-6-(4-methyl-styryl)-5-nitro-1H-pyrimidine-2,4-dione 
• 59119-42-5 1,3-dimethyl-6-(4-methyl-styryl)-5-nitro-1H-pyrimidine-2,4-dione 
• 85102-52-9 1,3-Dimethyl-5-nitro-6-(2-p-tolyl-ethyl)-1H-pyrimidine-2,4-dione 

Downstream Products

• 59119-46-9 1,3-dimethyl-6-p-tolyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione 

Relevant academic research and scientific papers

1,3-Dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines as potent A2B adenosine receptor antagonists: Design, synthesis, structure-affinity and structure-selectivity relationships

A number of 1,3-dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines were prepared and evaluated as ligands of recombinant human adenosine receptors (hARs). Several 1,3-dipropyl derivatives endowed with nanomolar binding affinity at hA2B receptors, but poor selectivity over hA2A, hA1 and hA3 AR subtypes were identified. A comparison with the corresponding 7-OH- and 7,9-unsubstituted-deazaxanthines revealed that 9-OH-9-deazaxanthines are more potent hA2B ligands with lower partition coefficients and higher water solubility compared to the other two congeneric classes of deazaxanthines. An optimization of the para-substituent of the 8-phenyl ring of 9-OH-9-deazaxanthines led to the discovery of compound 38, which exhibited outstanding hA2B affinity (Ki = 1.0 nM), good selectivity over hA2A, hA1 and hA3 (selectivity indices = 100, 79 and 1290, respectively) and excellent antagonist potency in a functional assay on rat A2B (pA2B = 9.33).

Fast and highly efficient one-pot synthesis of 9-deazaxanthines

SnCl2 enables a direct, high-yield conversion of 5-nitro-1,3-dialkyl-6-styryl(furyl-, thienyl-vinyl)-uracils to 8-substituted-9-deazaxanthines under very mild experimental conditions. The method has a general applicability and it is compatible with the reactivity of the most common organic functional groups. In slightly experimental different conditions, it allows a high-yield and fast (5 min) preparation of pure 7-N-hydroxy-9-deazaxanthines.

Pyrimidine Derivatives and Related Compounds. Part 47. A New Synthesis of Xanthines and Pyrrolopyrimidines by Intramolecular Cyclisation of 6-Substituted 5-Nitrouracil Derivatives

6-Arylalkylamino-1,3-dimethyl-5-nitrouracils (2a-f) were prepared by reaction of 6-chloro-1,3-dimethyl-5-nitrouracil (1) with arylalkylamines in the presence of triethylamine.Among them, the 6-arylalkylaminouracils (2a-d), possessing no substituent at the