14094-37-2

Usage

Chemical Properties

White Solid

InChI:InChI=1/C5H6BrN3O2.H2O/c1-9-3(7)2(6)4(10)8-5(9)11;/h7H2,1H3,(H,8,10,11);1H2

Upstream product

• 2434-53-9 6-amino-1-methyluracil 

Downstream Products

• 125092-42-4 6-amino-1-methyl-5-(propylamino)pyrimidine-2,4(1H,3H)-dione 
• 131598-62-4 6-Amino-5-ethylamino-1-methyl-1H-pyrimidine-2,4-dione 
• 131598-63-5 6-amino-5-(butylamino)-1-methylpyrimidine-2,4(1H,3H)-dione 
• 55441-70-8 6-amino-1-methyl-5-(methylamino)pyrimidine-2,4-dione 
• 70404-28-3 6-amino-5-(benzylamino)-1-methylpyrimidine-2,4(1H,3H)-dione 
• 876373-32-9 6-amino-5-(4-fluorophenethylamino)-1-methylpyrimidine-2,4(1H,3H)-dione 
• 6703-92-0 8-Mercaptotheobromin 
• 83-67-0 theobromine / 
• 15371-15-0 8-bromo-3,7-dimethylxanthine 
• 149981-18-0 3,7-dimethyl-8-phenylxanthine 
• 155588-82-2 3,7-Dimethyl-6-methylsulfanyl-8-phenyl-3,7-dihydro-purin-2-one 
• 149981-38-4 6-amino-1-methyl-5-methyl(phenyl)carboxamido-2,3-dioxo-1,2,3,4-tetrahydropyrimidine 
• 199680-97-2 3,7-dimethyl-8-styrylxanthine 
• 199680-96-1 1N-(6-amino-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-1N-methyl-3-phenyl-(E)-2-propenamide 

Relevant academic research and scientific papers

Preparation method of linagliptin for treating type II diabetes mellitus

The invention provides a preparation method of linagliptin for treating type II diabetes mellitus, which comprises the following steps: by using methylurea and ethyl cyanoacetate as raw materials, carrying out cyclization reaction to form a compound II, carrying out bromination reaction on the compound II to generate a compound III, carrying out condensation reaction on the compound III and 1-amino-2-butyne to generate a compound IV, making the compound IV, formic acid and an iodine source react in an organic solution to generate a compound V, reacting the compound V and a compound VI under the conditions of DMF and anhydrous potassium carbonate, reacting with (R)-3-Boc-aminopiperidine (VIII), and recrystallizing to obtain a pure target compound I, namely linagliptin. The invention provides a novel preparation method of linagliptin, which has the advantages of simple method, high reaction yield, avoidance of side reaction, cheap raw materials, reduction of the reaction cost, increase of the yield of the target compound, and suitableness for industrial large-scale production.

Discovery of MK-4688: An Efficient Inhibitor of the HDM2-p53 Protein-Protein Interaction

Identification of low-dose, low-molecular-weight, drug-like inhibitors of protein-protein interactions (PPIs) is a challenging area of research. Despite the challenges, the therapeutic potential of PPI inhibition has driven significant efforts toward this goal. Adding to recent success in this area, we describe herein our efforts to optimize a novel purine carboxylic acid-derived inhibitor of the HDM2-p53 PPI into a series of low-projected dose inhibitors with overall favorable pharmacokinetic and physical properties. Ultimately, a strategy focused on leveraging known binding hot spots coupled with biostructural information to guide the design of conformationally constrained analogs and a focus on efficiency metrics led to the discovery of MK-4688 (compound 56), a highly potent, selective, and low-molecular-weight inhibitor suitable for clinical investigation.

Discovery of the theobromine derivative MQS-14 that induces death of MGC-803 cells mainly through ROS-mediated mechanisms

Reactive oxygen species (ROS) play crucial roles in maintaining redox balance and regulating physiological processes, ROS levels in cancer cells are relatively higher than those in normal cells. Therefore, elevating cellular ROS levels may be a viable strategy for selective killing of cancer cells. In this work, we synthesized a series of new theobromine derivatives and evaluated their cytotoxicity against gastric cancer cells MGC-803, SGC-7901 and HGC-27. Particularly, MQS-14 potently inhibited cell growth of MGC-803, SGC-7901 and HGC-27 cells at low micromolar levels. Mechanistic studies showed that compound MQS-14 decreased cell viability of MGC-803 cells and inhibited cell division revealed by the CFDA and EdU staining assays. MQS-14 increased cellular ROS levels and activated the MAPK pathway accompanied by the decreased p-ERK and increased p-JNK expression. MQS-14 also induced DNA damage and apoptosis in MGC-803 cells. To conclude, MQS-14 induced cell death of MGC-803 cells partly through elevating cellular ROS levels.

Ligand-based design, synthesis and biological evaluation of xanthine derivatives as LSD1/KDM1A inhibitors

Histone lysine specific demethylase 1 (LSD1) has been recognized as an important epigenetic target for disease treatment. To date, a large number of LSD1 inhibitors have been developed, some of which are currently being evaluated in clinical trials for th

HYDROXYL PURINE COMPOUNDS AND USE THEREOF

Disclosed are a series of hydroxyl purine compounds and the use thereof as PDE2 or TNFα inhibitors, in particular, the compounds as shown in formula (I), or tautomers thereof or pharmaceutically acceptable salts thereof.

Xanthine LSD1 inhibitor and preparation method and application thereof

The invention belongs to the field of medicinal chemistry, and discloses a xanthine structure containing LSD1 inhibitor, a synthesizing method and related application. The xanthine LSD1 inhibitor is characterized in that the structure formula is shown in the description, wherein R1 is benzyl; R2 is 1-3 alkyl and carboxylic acid derivates; R3 is heteroatom substituted hexatomic ring. The LSD1 enzymatic activity detection result shows that the xanthine compound of such series is good in effect on inhibiting LSD1 and can be used as a lead compound, and on that basis, a novel LSD inhibitor is further designed (refer to Specification).

Hydroxypurine compound and use thereof

The invention discloses a hydroxypurine compound and a use of the hydroxypurine compound as a PDE2 or TNFa inhibitor and concretely discloses a compound shown in the formula (I) and its tautomer or pharmaceutically acceptable salt.

Fragment Discovery for the Design of Nitrogen Heterocycles as Mycobacterium tuberculosis Dihydrofolate Reductase Inhibitors

Fragment-based drug design was used to identify Mycobacterium tuberculosis (Mtb) dihydrofolate reductase (DHFR) inhibitors. Screening of ligands against the Mtb DHFR enzyme resulted in the identification of multiple fragment hits with IC50 values in the range of 38–90 μM versus Mtb DHFR and minimum inhibitory concentration (MIC) values in the range of 31.5–125 μg/mL. These fragment scaffolds would be useful for anti-tubercular drug design.

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

Activation of nuclear factor-kappa B (NF-κB) and related upstream signal transduction pathways have long been associated with the pathogenesis of a variety of inflammatory diseases and has recently been implicated in the onset of cancer. This report provi

Easy preparative scale syntheses of labelled xanthines: Caffeine, theophylline and theobromine

Several easy preparative scale (0.5-1.5 g) syntheses of deuterium labelled caffeine, theophylline and theobromine are described. Some new selective syntheses of theophylline and theobromine have been developed. Labelled xanthines are of great interest in qualitative or quantitative isotope dilution-mass spectrometry, coupled with gas or liquid chromatography, currently performed in anti-doping and forensic laboratories. Copyright