2434-53-9

Usage

Uses

Used in Pharmaceutical Applications:
6-Amino-1-methyluracil is used as an inhibitor for DNA repair glycosylase, playing a role in the development of pharmaceuticals that target DNA repair mechanisms.
Used in Chemical Synthesis:
6-Amino-1-methyluracil is used as a chemical intermediate in the preparation of complex organic compounds, such as 1,1'-di methyl-1H-spiro[pyrimido[4,5-b]quinoline-5,5'-pyrrolo[2,3-d]pyrimidine]-2,2',4,4',6'(1'H,3'H,3'H,7'H,1'H)-pentaone, via a reaction with isatin in the presence of catalytic p-toluene sulfonic acid.
Used in Flame Retardancy:
6-Amino-1-methyluracil is also utilized as a component in the flame retardant industry, where it contributes to the development of materials with enhanced fire-resistant properties.

InChI:InChI=1/C5H7N3O2/c1-8-3(6)2-4(9)7-5(8)10/h2H,6H2,1H3,(H,7,9,10)

Upstream product

• 873-83-6 4-Amino-2,6-dihydroxypyrimidine 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 6972-77-6 N-cyanoacetyl-N'-methyl-urea 
• 372-09-8 cyanoacetic acid 
• 598-50-5 N-Methylurea 
• 623-59-6 N-acetyl-N'-methylurea 
• 105-56-6 ethyl 2-cyanoacetate 
• 105-34-0 methyl 2-cyanoacetate 
• 96-31-1 N,N'-Dimethylurea 

Downstream Products

• 54058-36-5 6-amino-1-methyl-5-phenylazo-1H-pyrimidine-2,4-dione 
• 63981-33-9 6-amino-1-methyl-3-propyl-1,3-dihydropyrimidine-2,4-dione 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 14094-37-2 6-amino-5-bromo-1-methylpyrimidine-2,4(1H,3H)-dione 
• 96996-34-8 ethyl 1,2,3,4,5,8-hexahydro-1,7-dimethyl-5-(3-nitrophenyl)-2,4-dioxopyrido<2,3-d>pyrimidine-6-carboxylate 
• 6972-78-7 6-amino-1-methyl-5-nitrosouracil 
• 142168-86-3 1-methyl-6-nitropyrido<2,3-d>pyrimidine-2,4-dione 
• 2565-47-1 1-methyl-2,4,6-pyrimidinetrione 
• 439112-84-2 6-amino-1-methyl-3-(3-phenylpropyl)-1H-pyrimidine-2,4-dione 
• 439112-82-0 6-amino-1-methyl-3-benzyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

A uracil nitroso amine based colorimetric sensor for the detection of Cu2+ ions from aqueous environment and its practical applications

A simple uracil nitroso amine based colorimetric chemosensor (UNA-1) has been synthesized and screened for its cation recognition ability. Sensor UNA-1 exhibited a high sensitivity and selectivity towards Cu2+ ions in aqueous medium in the presence of a wide range of other competing cations (Ag+, Al3+, Ba2+, Ca2+, Cd2+, Co2+, Cr3+, Cs+, Fe2+, Fe3+, Li+, Mg2+, Mn2+, Na+, Ni2+, Pb2+, Zn2+, Hg2+ and Sr2+). With Cu2+, the sensor UNA-1 gave a distinct color change from colorless to dark yellow by forming a complex of 1:1 stoichiometry. Furthermore, sensor UNA-1 was successfully utilized in the preparation of test strips and supported silica for the detection of Cu2+ ions from aqueous environment.

An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium

Condensation of malonic acid 1 and ureas 2a-f proceeds smoothly in the presence of acetic anhydride 3 under microwave irradiation in solvent-free conditions to give 6-hydroxy-uracils 4 in excellent yields. Under identical conditions, the condensation of cyanoacetic acid 5 and ureas 2a,b,g and h in the presence of acetic anhydride 3, followed by cyclization in the presence of sodium hydroxide affords 6-amino-uracils 6 in high yields. The work-up procedures are simple and products need no purification.

Molecular and crystal structure of 5,6-diamino-1-methyluracil and 5,6-diamino-1,3-dimethyluracil monohydrate. Semiempirical calculations (AM1 and PM3) on 5,6-diaminouracil derivatives

The crystal and molecular structures of 5,6-diamino-1-methyluracil and 5,6-diamino-1,3-dimethyluracil monohydrate have been determined from X-ray diffraction. Both compounds are planar and the two amino groups have two different conformations. The substituent at the 5 position seems to be a true primary amino group with a strongly sp3 nitrogen, whereas the one at the 6 position is nearly coplanar with the uracil ring, displaying a predominant sp2 character. Semiempirical calculations were made on 5,6-diaminouracil, 5,6-diamino-2-thiouracil and their endocyclic N-methylated derivatives using the AM1 and PM3 hamiltonians. These indicate that the stability decreases on increasing methylation, the 2-thio compounds always being less stable than the 2-oxo ones.

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.

Linagliptin intermediate compound IV

The invention belongs to the field of pharmaceutical chemicals, and discloses a linagliptin intermediate IV and a novel route for synthesizing an important linagliptin intermediate from the linagliptin intermediate IV. The linagliptin intermediate IV synthesized in the invention has the advantages of high yield, simple operation, substantial reduction of production cost, suitableness for industrial production; and the synthesis route solves the problems of self-coupling of linagliptin intermediates and generation of large impurities in the prior art.

Synthesis, radiolabelling and initial biological characterisation of 18F-labelled xanthine derivatives for PET imaging of Eph receptors

Eph receptor tyrosine kinases, particularly EphA2 and EphB4, represent promising candidates for molecular imaging due to their essential role in cancer progression and therapy resistance. Xanthine derivatives were identified to be potent Eph receptor inhibitors with IC50 values in the low nanomolar range (1-40 nm). These compounds occupy the hydrophobic pocket of the ATP-binding site in the kinase domain. Based on lead compound 1, we designed two fluorine-18-labelled receptor tyrosine kinase inhibitors ([18F]2/3) as potential tracers for positron emission tomography (PET). Docking into the ATP-binding site allowed us to find the best position for radiolabelling. The replacement of the methyl group at the uracil residue ([18F]3) rather than the methyl group of the phenoxy moiety ([18F]2) by a fluoropropyl group was predicted to preserve the affinity of the lead compound 1. Herein, we point out a synthesis route to [18F]2 and [18F]3 and the respective tosylate precursors as well as a labelling procedure to insert fluorine-18. After radiolabelling, both radiotracers were obtained in approximately 5% radiochemical yield with high radiochemical purity (>98%) and a molar activity of >10 GBq μmol-1. In line with the docking studies, first cell experiments revealed specific, time-dependent binding and uptake of [18F]3 to EphA2 and EphB4-overexpressing A375 human melanoma cells, whereas [18F]2 did not accumulate at these cells. Since both tracers [18F]3 and [18F]2 are stable in rat blood, the novel radiotracers might be suitable for in vivo molecular imaging of Eph receptors with PET.

Linagliptin intermediate compound V

The invention belongs to the field of pharmaceutical chemicals, and provides a linagliptin intermediate compound V and an important intermediate for synthesizing linagliptin by using the intermediateV. The method solves the problems of self-coupling of linagliptin intermediates and generation of large impurities in the prior art, and the synthesized novel intermediate compound V has the advantages of high yield, simple operation, significantly reduced production cost, and suitableness for industrial production.

Xanthine compound and pharmaceutical composition and application thereof

The invention discloses a xanthine derivative as shown in the formula (I) and a pharmaceutical composition and application thereof. The xanthine derivative is prepared from a compound as shown in theformula (I) or a stereoisomer, a geometrical isomer, a hydrate or a solvate thereof, or a pharmaceutically acceptable salt or prodrug as shown in the description. The invention also relates to application of the compound as shown in the formula (I) and the pharmaceutical composition thereof as a DPP-4 inhibitor, and especially application in preparation of medicines for treating and/or preventingmetabolic disorder diseases such as diabetes.

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.

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 or pharmaceutically acceptable salts thereof.