53681-47-3

Usage

Uses

Used in Pharmaceutical Industry:
6-amino-1-propyluracil is used as a reactant for the preparation of pentoxifylline metabolite analogs, which are known for their anti-inflammatory properties. These analogs can be utilized in the development of new drugs to treat various inflammation-related conditions, such as arthritis, asthma, and other autoimmune diseases.
Used in Chemical Synthesis:
6-amino-1-propyluracil can also be used as a building block or intermediate in the synthesis of more complex organic molecules, particularly those with potential applications in the pharmaceutical, agrochemical, and material science industries. Its unique structure allows for further functionalization and modification, enabling the creation of novel compounds with specific properties and functions.

InChI:InChI=1/C7H11N3O2/c1-2-3-10-5(8)4-6(11)9-7(10)12/h4H,2-3,8H2,1H3,(H,9,11,12)

Upstream product

• 627-06-5 n-propylurea 
• 372-09-8 cyanoacetic acid 
• 105-56-6 ethyl 2-cyanoacetate 
• 41078-07-3 N-cyanoacetyl-N'-propyl-urea 

Downstream Products

• 63981-32-8 6-amino-3-ethyl-1-propylpyrimidine-2,4(1H,3H)-dione 
• 41078-02-8 3-propylxanthine 
• 183373-22-0 6-phenyl-1-propyl-7H-pyrrolo[2,3-d]pyrimidin-2,4(1H,3H)-dione 
• 1073238-78-4 8-azetidin-1-yl-1-(4-chlorobenzyl)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073238-92-2 1-(4-chlorobenzyl)-8-(1-hydroxyethyl)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-43-6 1-(4-chlorobenzyl)-8-(1-hydroxyethyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073238-77-3 1-(4-chlorobenzyl)-8-(dimethylamino)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073238-90-0 8-bromo-1-(4-chlorobenzyl)-7-methyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-50-5 C₁₅H₁₄BrClN₄O₂ 
• 1073238-93-3 1-(4-chlorobenzyl)-7,8-dimethyl-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-45-8 6-amino-3-(4-chlorobenzyl)-5-nitroso-1-propylpyrimidine-2,4(1H,3H)-dione 
• 1073239-44-7 5,6-diamino-3-(4-chlorobenzyl)-1-propylpyrimidine-2,4(1H,3H)-dione 
• 896420-11-4 1-(4-chlorobenzyl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione 
• 1073239-46-9 6-amino-3-(4-chlorobenzyl)-1-propylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Construction of Dihydropyrido[2,3- d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes

N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs.

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.

METHODS FOR THE SYNTHESIS OF 1,3-SUBSTITUTED AMINOURACILS AND OTHER XANTHINE-RELATED COMPOUNDS

Methods for the synthesis of disubstituted aminouracils and xanthine and/or xanthine-related compounds are provided.

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.

Approach to the library of fused pyridine-4-carboxylic acids by combes-type reaction of acyl pyruvates and electron-rich amino heterocycles

A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.

Diazinane Compounds

The present invention relates to novel compounds of the general formula (I) wherein R1, R2, R3 and R4 are as defined, having a positive allosteric GABAB receptor (GBR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABAB agonist, for the inhibition of transient lower esophageal sphincter relaxations, for the treatment of gastroesophageal reflux disease, as well as for the treatment of functional gastrointestinal disorders and irritable bowel syndrome (IBS).

XANTHINE COMPOUNDS HAVING A POSITIVE ALLOSTERIC GABAB RECEPTOR MODULATOR EFFECT

The present invention relates to novel xanthine compounds of the general formula (I) wherein R1, R2, R3 and R4 are as defined, having a positive allosteric GABA Breceptor (GBR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABA Bagonist, for the inhibition of transient lower esophageal sphincter relaxations, for the treatment of gastroesophageal reflux disease, as well as for the treatment of functional gastrointestinal disorders and irritable bowel syndrome (IBS).

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.

Immunosuppressive effects of 8-substituted xanthine derivatives

The invention relates to a novel use of 8-substituted xanthine derivatives for the manufacture of a medicament for the treatment of auto-immuno disorders.

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.