59119-41-4

Upstream product

• 55326-07-3 1,3,6-trimethyl-5-nitrouracil 
• 100-52-7 benzaldehyde 
• 19674-60-3 3,6-dimethyluracil 
• 13509-52-9 1,3,6-trimethyluracil 

Downstream Products

• 79186-66-6 6-cyano-1,3-dimethyl-5-nitro-6-styryl-5,6-dihydrouracil 
• 59119-44-7 1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione 
• 59119-48-1 9-hydroxy-8-phenyl-9-deazatheophylline 
• 85102-46-1 5-Hydroxy-1,3-dimethyl-6-phenyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione 
• 75997-52-3 4-(4-Methoxy-phenylamino)-1,3-dimethyl-6-phenyl-1,3-dihydro-pyrrolo[3,2-d]pyrimidin-2-one 
• 75997-51-2 4-(4-Bromo-phenylamino)-1,3-dimethyl-6-phenyl-1,3-dihydro-pyrrolo[3,2-d]pyrimidin-2-one 
• 75997-50-1 1,3-Dimethyl-6-phenyl-4-phenylamino-1,3-dihydro-pyrrolo[3,2-d]pyrimidin-2-one 
• 75997-53-4 5-benzylideneamino-1,3-dimethyl-6-phenethyluracil 
• 75997-54-5 6-chloro-6-deoxy-8-phenyl-9-deazatheophylline 
• 84637-39-8 4-Chloro-benzoic acid 1,3-dimethyl-2,4-dioxo-6-phenyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl ester 
• 84637-38-7 Benzoic acid 1,3-dimethyl-2,4-dioxo-6-phenyl-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl ester 
• 84637-42-3 9-acetoxy-8-phenyl-9-deazatheophylline 

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).

New pyrrolopyrimidin-6-yl benzenesulfonamides: Potent A2B adenosine receptor antagonists

A new series of 4-(1,3-dialkyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6 -yl)benzenesulfonamides has been identified as potent A2B adenosine receptor antagonists. The products have been evaluated for their binding affinities for the human A2B, A1 and A3 adenosine receptors. 6-(4-{[4-(4-Bromobenzyl)piperazin-1-yl]sulfonyl}phenyl)-1,3-dimethyl-1H- pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (16) showed a high affinity for the A2B adenosine receptor (IC50 = 1 nM) and selectivity (A1: 183x; A3: 12660x). Synthesis and SAR of this novel class of compounds showing improved absorption properties is presented herein.

NEW-4-(PYRROLOPYRIMIDIN-6-YL)BENZENESULPHONAMIDE DERIVATIVES

This invention is directed to new potent and selective antagonists of A2A and/or A2B adenosine receptors having the general formula (I) to process for their preparation; to pharmaceutical compositions comprising them; and to their us

Synthesis and structure-activity relationships of deazaxanthines: Analogs of potent A1- and A2-adenosine receptor antagonists

A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d]pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9- Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 1-3- fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2- naphthyl)-9-deazaxanthine (19e) showed high affinity (K(i) = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9- deazaxanthines was unfavorable for A1 and A2a receptor binding. 7- Deazaxanthines were considerably less potent compared to xanthines and to 9- deazaxanthines at both receptor subtypes.

NEW SYNTHESIS OF 1,3-DIMETHYL-7-HYDROXYPYRROLOPYRIMIDINE-2,4(1H,3H)-DIONES (9-HYDROXY-9-DEAZATHEOPHYLLINES)

Treatment of 5-nitro-1,3,6-trinitrouracil with aryl aldehydes in the presence of piperidine causes the condensation to the 5-nitro-6-styryl-uracil derivatives, followed by the intramolecular cyclization including piperidine-catalyzed oxidation-reduction t

Syntheses of 9-Deazatheophyllines and 6-Deoxy-9-deazatheophyllines

The reaction of 1,3-dimethyl-5-nitro-6-styryluracils (IIa-e) with sodium dithionite in formic acid afforded the corresponding 8-aryl-9-deazatheophyllines (IVa-e).The reaction of IVa with phosphorus oxychloride gave 6-chloro-6-deoxy-8-phenyl-9-deazatheophy