444058-30-4

Basic information

• Product Name: 5-benzoyl-1,3,6-triMethylpyriMidine-2,4(1H,3H)-dione
• Synonyms: 5-benzoyl-1,3,6-triMethylpyriMidine-2,4(1H,3H)-dione
• CAS NO: 444058-30-4
• Molecular Formula: C14H14N2O3
• Molecular Weight: 258.277
• EINECS: -0
• Mol File: 444058-30-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5-benzoyl-1,3,6-triMethylpyriMidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzoyl-1,3,6-triMethylpyriMidine-2,4(1H,3H)-dione(444058-30-4)
• EPA Substance Registry System: 5-benzoyl-1,3,6-triMethylpyriMidine-2,4(1H,3H)-dione(444058-30-4)

Safety Data

• Hazardous Substances Data: 444058-30-4(Hazardous Substances Data)

Upstream product

• 13509-52-9 1,3,6-trimethyluracil 
• 98-88-4 benzoyl chloride 
• 626-48-2 6-Methyluracil 

Downstream Products

• 931706-15-9 PPQ-102 
• 433971-83-6 6-(2-aminophenyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione 
• 1314872-72-4 7,9-dimethyl-6-(5-methylfuran-2-yl)-5-(methylsulfonyl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-73-5 5-(2-chloroacetyl)-7,9-dimethyl-6-(5-methylfuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-74-6 5-acetyl-7,9-dimethyl-6-(5-methylfuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-75-7 7,9-dimethyl-6-(5-methylfuran-2-yl)-5-nitroso-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-71-3 6-(N-methyl-2-aminophenyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione 
• 1314872-76-8 5,7,9-trimethyl-6-(5-methylfuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-77-9 7,9-dimethyl-6-(5-ethylfuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-78-0 7,9-dimethyl-6-(5-methylthiophene-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-79-1 7,9-dimethyl-6-(4,5-dimethylfuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-80-4 6-(5-chlorofuran-2-yl)-7,9-dimethyl-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-81-5 6-(5-bromofuran-2-yl)-7,9-dimethyl-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 
• 1314872-82-6 7,9-dimethyl-6-(5-iodofuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione 

Relevant articles and documents

Skeletally Diverse Synthesis of Innovative [2,1-c]-1,4-Oxazepine and [1,4]-Quinoxaline Systems

An efficient, innovative synthesis of [2,1-c]-1, 4-oxazepine and [1,4]-quinoxaline heterocycles along with the embodied pyrimido-pyrrolo motifs was established. Initially, the pyrrole ring was installed using microwave irradiation through an intramolecular base-catalyzed cyclization between acetyl bromomethyl pyrimidine dione and o-amino phenyl methanol or o-phenylenediamine methyl benzoates. Furthermore, oxazepine, and quinoxaline scaffolds were constructed by an acid-catalyzed condensation with a variety of aldehydes by an unconventional Pictet-Spengler reaction strategy. An important aspect of this work is to build novel heterocyclic ring systems with potential medicinal interest.

TRICYCLIC COMPOUNDS

The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof; and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

Nanomolar potency pyrimido-pyrrolo-quinoxalinedione CFTR inhibitor reduces cyst size in a polycystic kidney disease model

Inhibitors of the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel are predicted to slow cyst enlargement in polycystic kidney disease and reduce intestinal fluid loss in secretory diarrheas. Screening of ～110000 small synthetic and natural compounds for inhibition of halide influx in CFTR-expressing epithelial cells yielded a new class of pyrimido-pyrrolo-quinoxalinedione (PPQ) CFTR inhibitors. Testing of 347 analogues established structure-activity relationships. The most potent compound, 7,9-dimethyl-11-phenyl-6-(5-methylfuran-2-yl)-5,6-dihydro-pyrimido- [4′,5′-3,4]pyrrolo[1,2-a]quinoxaline-8,10-(7H,9H)-dione, PPQ-102, completely inhibited CFTR chloride current with IC50 ～90 nM. The PPQs, unlike prior CFTR inhibitors, are uncharged at physiological pH, and therefore not subject to membrane potential-dependent cellular partitioning or block efficiency. Patch-clamp analysis confirmed voltage-independent CFTR inhibition by PPQ-102 and showed stabilization of the channel closed state. PPQ-102 prevented cyst expansion and reduced the size of preformed cysts in a neonatal kidney organ culture model of polycystic kidney disease. PPQ-102 is the most potent CFTR inhibitor identified to date. 2009 American Chemical Society.