5169-95-9

Usage

Uses

Used in Food and Beverage Industry:
1,3-Diethyl-7H-purine-2,6(1H,3H)-dione is used as a stimulant and flavoring agent in various food and beverage products, such as coffee, tea, and energy drinks. It enhances alertness and concentration, making it a popular ingredient for consumers seeking a boost in cognitive performance and physical activity.
Used in Pharmaceutical Industry:
Caffeine is utilized as an active ingredient in some medications, particularly for treating headaches and migraines. It is also used in combination with pain relievers to enhance their effectiveness. Additionally, caffeine is present in some over-the-counter drugs to combat drowsiness and improve alertness.
Used in Cosmetics Industry:
1,3-Diethyl-7H-purine-2,6(1H,3H)-dione is employed in certain cosmetic products, such as eye creams and lotions, due to its vasoconstrictive properties. It helps to reduce the appearance of puffiness and dark circles under the eyes by tightening the skin and constricting blood vessels.
Used in Research and Scientific Applications:
Caffeine is also used in research settings as a model compound to study various biological processes and mechanisms. It serves as a tool to investigate the effects of adenosine receptor antagonism and its implications in different physiological and pathological conditions.

InChI:InChI=1/C9H12N4O2/c1-3-12-7-6(10-5-11-7)8(14)13(4-2)9(12)15/h5H,3-4H2,1-2H3,(H,10,11)

Upstream product

• 52998-22-8 5,6-diamino-1,3-diethyluracil 
• 74-96-4 ethyl bromide 
• 69-89-6 xanthin 
• 41740-15-2 6-amino-1,3-diethyluracil 
• 100144-09-0 N-(1,3-diethyl-6-amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-formamide 
• 623-76-7 N,N'-diethylurea 
• 89073-60-9 6-amino-1,3-diethyl-5-nitroso-1H,3H-pyrimidine-2,4-dione 
• 64-18-6 formic acid 
• 454710-33-9 7-benzyl-1,3-diethyl-1,3,7-trihydropurine-2,6-dione 

Downstream Products

• 31542-51-5 1,3-diethyl-7-(2-hydroxy-ethyl)-3,7-dihydro-purine-2,6-dione 
• 86257-64-9 1,3-diethyl-7-(6,7-isopropylidenedioxyheptyl)xanthine 

Relevant academic research and scientific papers

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 method of 1,3-diethyl-3,7-dihydropurine-2,6-diketone

The invention relates to a synthesis method of 1,3-diethyl-3,7-dihydropurine-2,6-diketone. The method provided by the invention can solve the technical problems that by the existing synthesis method, sodium hydrosulfite powder is used for reducing to cause unstable yield and high environmental pollution as well as an expensive metal catalyst is used to cause that the raw material cost is high and noble metal recovery is difficult to control. The synthesis method provided by the invention comprises the following steps: performing cyclization reaction under the participation of 1,3-diethyl urea and cyanoacetic acid to obtain 6-amido-1,3-diethyl-1H-pyrimidine-2,4-diketone; performing electrophilic addition reaction on the 6-amido-1,3-diethyl-1H-pyrimidine-2,4-diketone and sodium nitrite under the condition of organic acid to obtain 6-amido-1,3-diethyl-5-nitroso-1H-pyrimidine-2,4-diketone; performing reduction and acylation reaction under the action of zinc powder and formic acid to obtain N-(6-amido-1,2,4-diethyl-1,2,3,4-tetrahydropyrimidine-5-yl)-formamide; performing ring closing under the condition of strong alkali, and performing acidification to obtain the 1,3-diethyl-3,7-pyrimidine-2,6-diketone. The compound is an important medicine compound early-stage raw material and intermediate in the field of research on various new medicines.

Palladium(II)-catalyzed oxidative C-H/C-H cross-coupling of heteroarenes

(Chemical Presented) An efficient methodology for the synthesis of unsymmetrical biheteroaryl molecules has been developed via Pd(II)-catalyzed oxidative C-H/C-H cross-coupling of heteroarenes. An inversion in reactivity and selectivity has been achieved

Design and synthesis of xanthine analogues as potent and selective PDE5 inhibitors

We have discovered potent and selective xanthine PDE5 inhibitors. Compound 25 (PDE5 IC50=0.6 nM, PDE6/PDE5=101) demonstrated similar functional efficacy and PK profile to Sildenafil (PDE5 IC50=3.5 nM, PDE6/PDE5=7).

Xanthines, optionally incorporated in liposomes, for promoting skin or hair pigmentation

A method of treating skin or hair for promoting pigmentation wherein a xanthine component, in an amount effective to promote pigmentation, is incorporated in liposomes or hydrated lipidic lamellar phases.