6972-82-3

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Diamino-1-methyluracil is used as a key intermediate in the synthesis of tyrosine kinase erythropoietin inhibitors, which are crucial for the development of targeted therapies against hepatocellular carcinoma receptor B4 (EphB4). These inhibitors can help regulate the activity of tyrosine kinases, which play a significant role in cell growth, differentiation, and apoptosis, and are often dysregulated in cancer cells.
In the development of novel therapeutic agents, 5,6-Diamino-1-methyluracil can be utilized to create molecules with enhanced selectivity, potency, and reduced side effects. Its unique structural features allow for the design of compounds that can specifically target EphB4 receptors, which are implicated in various cancer-related processes, including tumor growth, angiogenesis, and metastasis.
Furthermore, 5,6-Diamino-1-methyluracil can also be employed in the synthesis of other bioactive molecules with potential applications in various therapeutic areas, such as antiviral, antibacterial, and anti-inflammatory agents. Its versatility in chemical modifications and conjugations makes it a valuable building block for the development of innovative drug candidates.

InChI:InChI=1/C5H8N4O2/c1-9-3(7)2(6)4(10)8-5(9)11/h6-7H2,1H3,(H,8,10,11)

Upstream product

• 54058-36-5 6-amino-1-methyl-5-phenylazo-1H-pyrimidine-2,4-dione 
• 6972-78-7 6-amino-1-methyl-5-nitrosouracil 
• 2434-53-9 6-amino-1-methyluracil 
• 50996-12-8 6-amino-1-methyl-5-nitro-1H-pyrimidine-2,4-dione 
• 6972-77-6 N-cyanoacetyl-N'-methyl-urea 

Downstream Products

• 1076-22-8 3-methylxanthine 
• 14785-95-6 3-methyl-4-amino-5-formylamino-2,6-dioxypyrimidine 
• 605-99-2 3-methyluric acid 
• 55441-55-9 (6-amino-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-carbamic acid ethyl ester 
• 50256-18-3 1-methyl-2,4-dioxo-(1H,3H)pteridine 
• 19845-24-0 1-methyl-6,7-diphenyllumazine 
• 50256-21-8 1,6,7-trimethyl-2,4-dioxo-(1H,3H)pteridine 
• 62700-61-2 4-methyl-4H-[1,2,5]thiadiazolo[3,4-d]pyrimidine-5,7-dione 
• 25716-27-2 4-amino-3-methyl-6,7-diphenyl-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-2-one 
• 172751-05-2 6,7-diethyl-1-methylpteridine-2,4-dione 
• 343362-39-0 6-amino-1-methyl-5-[3-phenyl-(E,2E)-2-propenylidenamino]-1,2,3,4-tetrahydro-2,4-pyrimidindione 
• 543700-00-1 6-amino-1-methyl-5-[(2,3,5-tichlorobenzylidene)amino]-1H-pyrimidin-2,4-dione 
• 61885-33-4 6-Amino-5-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-1-methyl-1H-pyrimidine-2,4-dione 
• 61885-32-3 6-Amino-1-methyl-5-{[1-phenyl-meth-(E)-ylidene]-amino}-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and bio-evaluation of a novel selective butyrylcholinesterase inhibitor discovered through structure-based virtual screening

In recent years, butyrylcholinesterase (BChE) has gradually gained worldwide interests as a novel target for treating Alzheimer's disease (AD). Here, two pharmacophore models were generated using Schr?dinger suite and used to virtually screen ChemDiv database, from which three hits were obtained. Among them, 2513–4169 displayed the highest inhibitory activity and selectivity against BChE (eeAChE IC50 > 10 μM, eqBChE IC50 = 3.73 ± 1.90 μM). Molecular dynamic (MD) simulation validated the binding pattern of 2513–4169 in BChE, and it could form a various of receptor-ligand interactions with adjacent residues. In vitro cytotoxicity assay proved the safety of 2513–4169 on diverse neural cell lines. Moreover, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay performed on SH-SY5Y cells proved the neuroprotective effect of 2513–4169 against toxic Aβ1–42. In vivo behavioral study further confirmed the great efficacy of 2513–4169 on reversing Aβ1–42-induced cognitive impairment of mice and clearing the toxic Aβ1–42 in brains. Moreover, 2513–4169 was proved to be able to cross blood-brain barrier (BBB) through a parallel artificial membrane permeation assay of BBB (PAMPA-BBB). Taken together, 2513–4169 is a promising lead compound for future optimization to discover anti-AD treating agents.

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.

Novel, Dual Target-Directed Annelated Xanthine Derivatives Acting on Adenosine Receptors and Monoamine Oxidase B

Annelated purinedione derivatives have been shown to act as possible multiple-target ligands, addressing adenosine receptors and monoaminooxidases. In this study, based on our previous results, novel annelated pyrimido- and diazepino[2,1-f]purinedione derivatives were designed as dual-target-directed ligands combining A2A adenosine receptor (AR) antagonistic activity with blocking monoamine oxidase B. A library of 19 novel compounds was synthesized and biologically evaluated in radioligand binding studies at AR subtypes and for their ability to inhibit MAO-B. This allowed 9-(2-chloro-6-fluorobenzyl)-3-ethyl-1-methyl-6,7,8,9-tetrahydropyrimido[2,1-f]purine-2,4(1H,3H)-dione (13 e; Ki human A2AAR: 264 nM and IC50 human MAO-B: 243 nM) to be identified as the most potent dual-acting ligand from this series. ADMET parameters were estimated in vitro, and analysis of the structure-activity relationships was complemented by molecular-docking studies based on previously published X-ray structures of the protein targets. Such dual-acting ligands, by selectively blocking A2A AR, accompanied by the inhibition of dopamine metabolizing enzyme MAO-B, might provide symptomatic and neuroprotective effects in, among others, the treatment of Parkinson disease.

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.

For the treatment of diabetes type II a pharmaceutical intermediates preparation method (by machine translation)

The invention belongs to the technical field of chemical industry, and in particular relates to a medicament for the treatment of diabetes type II intermediate preparation method. The invention to PdCl2 . 2 H2 O and ammonium metatungstate as precursor, the silicon nitride film as the catalyst carrier, depositing a - precipitation method to prepare a new kind of ammonium metatungstate modified palladium metal catalyst; said catalyst can be used for catalytic 6 - amino - 5 - nitroso - 1 - methyl uracil reduction preparation of 5, 6 - diamino - 1 - methyl uracil, high selectivity and conversion, green is pollution-free; at the same time the materials can be added one time, avoiding the traditional sodium dithionite reduction system batch add to the shortcoming of the operating requirement is high. (by machine translation)

Substituted xanthine compound and its preparation and use (by machine translation)

The invention discloses substituted xanthine compounds, a preparation method and applications thereof, and specifically relates to compounds represented by the formula (I), stereo isomers and pharmaceutically acceptable salts thereof, wherein the R1 and R2 are defined in the description. The invention also relates to a pharmaceutical composition containing the compounds, an application of the pharmaceutical composition in preparation of drugs for treating diseases or symptoms caused by high activity of DPP-IV or overexpression of DPP-IV, and a method using the pharmaceutical composition to treat related diseases. The provided compounds can effectively inhibit the activity of DPP-IV.

7,8-substituted-3-methylxanthine compounds as well as preparation method and application thereof

The invention discloses 7,8-substituted-3-methylxanthine compounds as well as a preparation method and an application thereof. The compounds have the structural formula (I) shown in the description, wherein R is aliphatic hydrocarbon, an aromatic ring, an acyl-containing group, a hydroxyl-containing group or a sulfhydryl-containing group; R1 is C1-4 alkyl, halogen substituted C1-4 alkyl, C1-4 alkoxy, halogen, a cyano group, nitryl, acetyl, benzyl, benzyloxy, substituted or unsubstituted C1-4 alkylbenzene, a substituted or unsubstituted amino group, substituted guanidyl, a substituted or unsubstituted phosphate group, a substituted or unsubstituted sulfonic group, a substituted or unsubstituted long-chain fatty alkane or substituted or unsubstituted long-chain fatty amine. The compounds have good inhibition effects on PDE8 (phosphodiesterase type 8), PDE8 is also a potential target of the alzheimer's disease, vascular dementia and diabetes, the compounds take PDE8 as the target, and a drug prepared from the compounds has a better curative effect on alzheimer's disease, vascular dementia and diabetes as well.

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.