53681-49-5

Usage

Uses

Used in Pharmaceutical Industry:
6-AMINO-1-BUTYL-1H-PYRIMIDINE-2,4-DIONE is used as a key intermediate compound for the synthesis of molecules with A2B adenosine receptor antagonistic activity. These molecules have potential therapeutic applications in treating various diseases and conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and other inflammatory disorders, by modulating the adenosine signaling pathway.

InChI:InChI=1/C8H13N3O2/c1-2-3-4-11-6(9)5-7(12)10-8(11)13/h5H,2-4,9H2,1H3,(H,10,12,13)

Upstream product

• 36981-01-8 N-butyl-N'-cyanoacetylurea 
• 592-31-4 1-butyl-urea 
• 105-56-6 ethyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 53681-50-8 6-amino-1-butyl-3-methyluracil 
• 133657-16-6 1-Butyl-7-methyl-5-(3-nitro-phenyl)-2,4-dioxo-1,2,3,4,5,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methyl ester 
• 628279-11-8 6-amino-1-butyl-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione 
• 161419-78-9 6-amino-3-benzyl-1-butyluracil 
• 131000-85-6 1-Butyl-6-ethoxycarbonyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4,5,8-hexahydro-pyrido(2,3-d)pyrimidine 
• 637335-60-5 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester 
• 637335-58-1 2-(4-acetylamino-phenyl)-N-(6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide 
• 637335-59-2 N-[4-(3-butyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-phenyl]-acetamide 
• 637335-61-6 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-(2-fluoro-5-nitro-benzyl)-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester 
• 637335-62-7 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-1-(5-amino-2-fluoro-benzyl)-3-butyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester 
• 637335-63-8 2,2-dimethyl-propionic acid 8-(4-acetylamino-benzyl)-3-butyl-1-(2-fluoro-5-methoxy-benzyl)-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester 
• 637335-65-0 N-{4-[3-butyl-1-(2-hydroxy-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl }-acetamide 
• 133689-51-7 methyl 1,3,8-tributyl-1,2,3,4,5,8-hexahydro-7-methyl-5-(3-nitrophenyl)-2,4-dioxopyrido<2,3-d>pyrimidine-6-carboxylate 
• 133689-49-3 methyl 1,3-dibutyl-1,2,3,4,5,8-hexahydro-7-methyl-5-(3-nitrophenyl)-2,4-dioxopyrido<2,3-d>pyrimidine-6-carboxylate 

Relevant academic research and scientific papers

XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS

This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.

Exploring Selective Inhibition of the First Bromodomain of the Human Bromodomain and Extra-terminal Domain (BET) Proteins

A midthroughput screening follow-up program targeting the first bromodomain of the human BRD4 protein, BRD4(BD1), identified an acetylated-mimic xanthine derivative inhibitor. This compound binds with an affinity in the low micromolar range yet exerts suitable unexpected selectivity in vitro against the other members of the bromodomain and extra-terminal domain (BET) family. A structure-based program pinpointed a role of the ZA loop, paving the way for the development of potent and selective BET-BRDi probes.

Carboxylic acid-catalyzed one-pot synthesis of cyanoacetylureas and their cyclization to 6-aminouracils in guanidine ionic liquid

A novel, one-pot, carboxylic acid-catalyzed synthesis of cyanoacetylureas via in situ generated ureas and their cyclization to 6-aminouracils in the presence of the guanidine-based ionic liquid 1,1,3,3-tetramethylguanidine lactate [TMG][Lac] is described. The ureas were synthesized from amines and potassium cyanate, which on reaction with cyanoacetic acid in the presence of acetic anhydride in the same pot afforded cyanoacetylureas, which undergo cyclization in [TMG][Lac] as solvent as well as catalyst to afford 6-aminouracils. One-pot synthesis of cyanoacetylureas, efficient and rapid cyclization, better yield, shorter reaction time, easy workup procedure, and recyclability of the ionic liquid are some advantages of this procedure.

Ionic liquid mediated one-pot synthesis of 6-aminouracils

A novel, one-pot synthesis of 6-aminouracils via in situ generated ureas and cyanoacetylureas in the presence of an ionic liquid catalyst, 1,1,3,3-tetramethylguanidine acetate, is described. The catalyst can be recycled for five consecutive runs without loss of activity. The mechanism for the ring closure of cyanoacetylurea to 6-aminouracil is also discussed.

Selective, high affinity A2B adenosine receptor antagonists: N-1 monosubstituted 8-(pyrazol-4-yl)xanthines

A series of N-1 monosubstituted 8-pyrazolyl xanthines have been synthesized and evaluated for their affinity for the adenosine receptors (AdoRs). We have discovered two compounds 18 (CVT-7124) and 28 (CVT-6694) that display good affinity for the A2B AdoR (Ki = 6 nM and 7 nM, respectively) and greater selectivity for the human A1, A2A, and A3 AdoRs (>1000-, >830-, and >1500-fold; >850-, >700-, and >1280-fold, respectively). CVT-6694 has been shown to block the release of interleukin-6 and monocyte chemotactic protein-1 from bronchial smooth muscle cells (BSMC), a process believed to be promoted by activation of A2B AdoR.

Amide substituted xanthine derivatives

The present invention is a 1,3,8 substituted xanthine derivative of formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2 and R3 are as defined in the specification. Compounds of formula I and pharmaceutically acceptable salts or prodrugs thereof show activity as modulators of gluconeogenesis.

XANTHINE DERIVATIVES AS A2B ADENOSINE RECEPTOR ANTAGONISTS

Disclosed are compounds that are A2B adenosine receptor antagonists, useful for treating various disease states, including asthma and diarrhea.

AMIDE SUBSTITUTED XANTHINE DERIVATIVES WITH GLUCONEOGENESIS MODULATING ACTIVITY

The present invention is a 1,3,8 substituted xanthine derivative of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1, R2 and R3 are as defined in the specification. Compounds of formula (I) and pharmaceutically acceptable salts or prodrugs thereof show activity as modulators of gluconeogenesis.

A2B adenosine receptor antagonists

Disclosed are novel compounds that are A2B adenosine receptor antagonists, useful for treating various disease states, including asthma and diarrhea.

Di- or trisubstituted xanthines with neuroleptic properties and composition

The invention relates to xanthines corresponding to the formula STR1 and physiologically acceptable salts thereof, in which R1 represents C2 -C4 -alkyl, C3 -C4 -isoalkyl, CH2 -(C2 -C3 -alkenyl) or CH2 -(C3 -isoalkenyl); R3 represents C3 -C5 -alkyl, C3 -C5 -isoalkyl, CH2 -(C2 -C4 -alkenyl) or CH2 -(C3 -C4 -isoalkenyl); R8 represents H, methyl or ethyl; with the proviso that (1) when R8 represents H, R1 is allyl and (2) R1 and R3 cannot both represent butyl or allyl at the same time. The compounds show non-specific or anxiolytic sedative activity.