157119-69-2

Basic information

• Product Name: 6-Phenyl-1,3-dipropyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione
• Synonyms: 6-Phenyl-1,3-dipropyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione
• CAS NO: 157119-69-2
• Molecular Weight: 311.384
• Mol File: 157119-69-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 6-Phenyl-1,3-dipropyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Phenyl-1,3-dipropyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione(157119-69-2)
• EPA Substance Registry System: 6-Phenyl-1,3-dipropyl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione(157119-69-2)

Safety Data

• Hazardous Substances Data: 157119-69-2(Hazardous Substances Data)

Upstream product

• 62899-00-7 6-methyl-1,3-dipropyluracil 
• 157119-79-4 6-methyl-5-nitro-1,3-dipropyl-1H-pyrimidine-2,4-dione 
• 7454-99-1 6-methyl-3-propyluracil 
• 157119-86-3 5-nitro-1,3-dipropyl-6-styryl-1H-pyrimidine-2,4-dione 
• 548942-89-8 5-nitro-1,3-dipropyl-6-styryluracil 

Relevant articles and documents

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).

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

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.