5169-95-9

Basic information

• Product Name: 1,3-Diethyl-7H-purine-2,6(1H,3H)-dione
• Synonyms: 1,3-Diethyl-3,7-dihydro-1H-purine-2,6-dione;1,3-Diethyl-7H-purine-2,6(1H,3H)-dione;1,3-Diethylxantine
• CAS NO: 5169-95-9
• Molecular Formula: C₉H₁₂N₄O₂
• Molecular Weight: 208.2172
• Mol File: 5169-95-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 451.2°Cat760mmHg
• Flash Point: 226.7°C
• Appearance: /
• Density: 1.317g/cm³
• Vapor Pressure: 2.49E-08mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 1,3-Diethyl-7H-purine-2,6(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Diethyl-7H-purine-2,6(1H,3H)-dione(5169-95-9)
• EPA Substance Registry System: 1,3-Diethyl-7H-purine-2,6(1H,3H)-dione(5169-95-9)

Safety Data

• Hazardous Substances Data: 5169-95-9(Hazardous Substances Data)

Usage

General Description

1,3-Diethyl-7H-purine-2,6(1H,3H)-dione, also known as caffeine, is a natural stimulant found in coffee, tea, and chocolate. It belongs to the class of compounds known as xanthines, and its chemical structure consists of a purine ring with two ethyl groups attached at the 1 and 3 positions, and two carbonyl groups at the 2 and 6 positions. Caffeine works by blocking the action of adenosine, a neurotransmitter that promotes relaxation and sleepiness. As a result, it increases alertness and reduces the perception of fatigue. Caffeine is also known for its ability to improve concentration, enhance physical performance, and elevate mood. However, excessive consumption can lead to negative side effects, including anxiety, insomnia, and increased heart rate.

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

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

Downstream Products

• 86257-64-9 1,3-diethyl-7-(6,7-isopropylidenedioxyheptyl)xanthine 
• 865452-34-2 8-bromo-1,3-diethyl-7-(3-methoxy-benzyl)-3,7-dihydro-purine-2,6-dione 

Relevant articles and documents

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.

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

XANTHINES IN THE 7TH POSITION WITH A BENZYL ACETIC ACID MOIETY

-