59119-44-7

Upstream product

• 85102-46-1 5-Hydroxy-1,3-dimethyl-6-phenyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione 
• 59119-41-4 1,3-dimethyl-5-nitro-6-styryluracil 
• 61541-41-1 6-azido-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 59119-41-4 1,3-dimethyl-5-nitro-6-styryl-1H-pyrimidine-2,4-dione 
• 19674-60-3 3,6-dimethyluracil 
• 13509-52-9 1,3,6-trimethyluracil 
• 55326-07-3 1,3,6-trimethyl-5-nitrouracil 
• 100-44-7 benzyl chloride 
• 85102-51-8 1,3-dimethyl-5-nitro-6-phenethyluracil 
• 100-39-0 benzyl bromide 
• 79186-63-3 6-ethyl-1,3-dimethyl-5-nitrouracil 
• 100-52-7 benzaldehyde 

Downstream Products

• 75997-52-3 4-(4-Methoxy-phenylamino)-1,3-dimethyl-6-phenyl-1,3-dihydro-pyrrolo[3,2-d]pyrimidin-2-one 
• 83848-77-5 7-formyl-1,3-dimethyl-6-phenylpyrrolo<3,2-d>pyrimidine-2,4(1H,3H)-dione 
• 75997-50-1 1,3-Dimethyl-6-phenyl-4-phenylamino-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 
• 75997-54-5 6-chloro-6-deoxy-8-phenyl-9-deazatheophylline 
• 612095-43-9 4-(1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl)-benzenesulphonyl chloride 

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.

8-Substituted-9-deazaxanthines as adenosine receptor ligands: Design, synthesis and structure-affinity relationships at A2B

A number of 8-substituted-9-deazaxanthine derivatives (1,3-dialkyl-6- substituted-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-diones) were prepared and tested for their antagonistic activity at the recombinant human adenosine receptors, in particular at the A

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

A facile synthesis of pyrrolo-[3,2-d]pyrimidines from 6-azidouracils and ylide phosphoranes

A series of the title compounds, 9-deazaxanthines, was regioselectively prepared in reasonable yields as major products from the reactions of 6-azidouracils 1a,b with stabilized ester-2a,b or keto-2c ylide phosphoranes and a moderated phosphorus ylide 3, instead of the expected triazoles. Side products were also observed wherein pyrimido[5,4-g]pteridine-2,4,5,7-tetrone (15) and other fused ring systems or acyclic-substituted uracil derivatives were isolated. A comparative study on the reactivity of 1a in analogy to 1b toward phosphoranes is also described.

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.

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

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