142665-13-2

Basic information

• Product Name: 5,6-DiaMino-3-propylpyriMidine-2,4(1H,3H)-dione
• Synonyms: 5,6-DiaMino-3-propylpyriMidine-2,4(1H,3H)-dione;3-Propyl-5,6-diaminouracil
• CAS NO: 142665-13-2
• Molecular Formula: C₇H₁₂N₄O₂
• Molecular Weight: 184.19578
• Mol File: 142665-13-2.mol

Chemical Properties

• Appearance: /
• Density: 1.269±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 11.59±0.40(Predicted)
• CAS DataBase Reference: 5,6-DiaMino-3-propylpyriMidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DiaMino-3-propylpyriMidine-2,4(1H,3H)-dione(142665-13-2)
• EPA Substance Registry System: 5,6-DiaMino-3-propylpyriMidine-2,4(1H,3H)-dione(142665-13-2)

Safety Data

• Hazardous Substances Data: 142665-13-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione is used as a key intermediate in the synthesis of various drugs, particularly those with antiviral and antineoplastic properties. Its ability to inhibit the growth of cancer cells and its antiviral activity against certain viruses make it a valuable asset in the development of new pharmaceutical drugs.
Used in Research and Development:
In the realm of biochemical and medical studies, 5,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione serves as a research reagent. It is utilized to explore its potential therapeutic applications and to understand the mechanisms of action that underpin its biological effects. This research is crucial for advancing the knowledge of its role in treating various diseases and for identifying new avenues for its application in medicine.

Upstream product

• 110472-90-7 6-amino-3-propyluracil 
• 146830-67-3 6-amino-5-nitroso-3-propyluracil 

Downstream Products

• 1188541-69-6 8-{1-[3-(3-fluorophenyl)prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-3,7-dihydropurine-2,6-dione 
• 1188541-68-5 8-{1-[3-(4-fluorophenyl)prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-3,7-dihydropurine-2,6-dione 
• 1188541-66-3 1-propyl-8-{1-[3-(3-trifluoromethylphenyl)prop-2-ynyl]-1H-pyrazol-4-yl}-3,7-dihydropurine-2, 6-dione 
• 1188541-70-9 1-propyl-8-{1-[3-(4-trifluoromethylphenyl)prop-2-ynyl]-1H-pyrazol-4-yl}-3,7-dihydropurine-2,6-dione 
• 1188541-67-4 1-propyl-8-{1-[3-(3-trifluoromethoxyphenyl)prop-2-ynyl]-1H-pyrazol-4-yl}-3,7-dihydropurine-2,6-dione 
• 1188541-72-1 1-propyl-8-{1-[3-(4-trifluoromethoxyphenyl)prop-2-ynyl]-1H-pyrazol-4-yl}-3,7-dihydropurine-2,6-dione 
• 1188541-73-2 3-{3-[4-(2,6-dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)pyrazol-1-yl]prop-1-ynyl}benzoic acid 
• 174519-00-7 6-amino-5-(3-chlorocinnamoylamino)-3-propyluracil 
• 104285-82-7 1-Propylxanthine 
• 152529-72-1 6-amino-3-propyl-5-(4-sulfophenyl)carboxamidouracil 
• 152529-70-9 Cyclopentane carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetra hydro-pyrimidin-5-yl)-amide 
• 1188543-38-5 1-[5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid {6-amino-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl}-amide 
• 1188543-39-6 3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-8-{1-[5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-1-propyl-3,7-dihydro-purine-2,6-dione 
• 1188543-33-0 3-(2-amino-ethyl)-8-{1-[5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-1-propyl-3,7-dihydro-purine-2,6-dione 

Relevant articles and documents

Fluorescent-Labeled Selective Adenosine A2B Receptor Antagonist Enables Competition Binding Assay by Flow Cytometry

Fluorescent ligands represent powerful tools for biological studies and are considered attractive alternatives to radioligands. In this study, we developed fluorescent antagonists for A2B adenosine receptors (A2BARs), which are targeted by antiasthmatic xanthines and were proposed as novel targets in immuno-oncology. Our approach was to merge a small borondipyrromethene (BODIPY) derivative with the pharmacophore of 8-substituted xanthine derivatives. On the basis of the design, synthesis, and evaluation of model compounds, several fluorescent ligands were synthesized. Compound 29 (PSB-12105), which displayed high affinity for human, rat, and mouse A2BARs (Ki = 0.2-2 nM) and high selectivity for this AR subtype, was selected for further studies. A homology model of the human A2BAR was generated, and docking studies were performed. Moreover, 29 allowed us to establish a homogeneous receptor-ligand binding assay using flow cytometry. These compounds constitute the first potent, selective fluorescent A2BAR ligands and are anticipated to be useful for a variety of applications.

Synthesis and pharmacological evaluation of novel 1,3,8- and 1,3,7,8-substituted xanthines as adenosine receptor antagonists

A number of novel xanthines bearing a variety of substituents at positions 1, 3, 7 and 8 were prepared and evaluated for their binding affinity to the human adenosine receptor A1, A2A, A2B and A3 subtypes. Several of the 1,3,8- and 1,3,7,8-substituted xanthines showed moderate-to-high affinity at human A2B and A1 receptors, with the most active compound (14q) having a pKi of 7.57 nM for hA2B receptors and a selectivity over hA2A receptors of 8.1-fold and hA1 receptors of 3.7-fold.

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.

METHOD OF PREVENTING AND TREATING HEPATIC DISEASE USING A2B ADENOSINE RECEPTOR ANTAGONISTS

The invention is related to methods of preventing and treating hepatic fibrosis using A2B adenosine receptor antagonists and utility in the treatment and prevention of liver damage caused by alcohol abuse, surgical intervention, viral hepatitis, the ingestion of hepatotoxic drugs, or other hepatic diseases. The invention also relates to pharmaceutical compositions for use in the method.

Method of wound healing using A2B adenosine receptor antagonists

The present invention relates to methods of wound healing using A2B adenosine receptor antagonists. The invention also relates to methods for the preparation of such compounds, and to pharmaceutical compositions containing them.

METHOD OF PREVENTING AND TREATING AIRWAY REMODELING AND PULMONARY INFLAMMATION USING A2B ADENOSINE RECEPTOR ANTAGONISTS

The present invention relates to methods of preventing airway remodeling using A2B adenosine receptor antagonists. This invention finds utility in the treatment and prevention of asthma, COPD, pulmonary fibrosis, emphysema, and other pulmonary diseases. The invention also relates to pharmaceutical compositions for use in the method.

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.

A2B adenosine receptor antagonists

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

A2B adenosine receptor antagonists

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

A new versatile synthesis of xanthines with variable substituents in the 1-, 3-, 7- and 8-positions

A new convenient procedure for the synthesis of a wide range of xanthines has been developed starting from 3-substituted 6-aminouracils. Nitrosation and reduction yields the corresponding 5,6-diaminouracils, which are condensed with carboxylic acids. The resulting amides can be selectively alkylated at the uracil ring nitrogen N-1 (corresponding to xanthine N-3) under mild conditions. Ring closure and, if desired, alkylation at the 7-position, yields di-, tri-, or tetrasubstituted xanthines in high yields. Sensitive substituents, such as prop-2-ynyl, can be introduced in the 1-position. Variation of the 3-substituent is considerably facilitated in comparison with the standard procedure for the preparation of xanthines.