2565-43-7

Basic information

• Product Name: 5-allylbarbituric acid
• Synonyms: 5-allylbarbituric acid;5-(2-Propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione;5-prop-2-enyl-1,3-diazinane-2,4,6-trione
• CAS NO: 2565-43-7
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.15002
• EINECS: 219-893-5
• Mol File: 2565-43-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.225g/cm³
• Refractive Index: 1.483
• PKA: pK1: 4.78(+1) (25°C)
• CAS DataBase Reference: 5-allylbarbituric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-allylbarbituric acid(2565-43-7)
• EPA Substance Registry System: 5-allylbarbituric acid(2565-43-7)

Safety Data

• Hazardous Substances Data: 2565-43-7(Hazardous Substances Data)

Usage

General Description

5-allylbarbituric acid, also known as 5-allyl-6-methyluracil or allylisobarbital, is a chemical compound that belongs to the barbiturate class of drugs. It is a derivative of barbituric acid and has been found to exhibit sedative and hypnotic properties. 5-allylbarbituric acid has been studied for its potential use as an anticonvulsant and anesthetic, although it has limited medical applications due to its side effects and potential for abuse. 5-allylbarbituric acid is also used as a chemical intermediate in the synthesis of other pharmaceuticals and has been studied for its potential use in the treatment of central nervous system disorders. However, its use is limited due to its potential for tolerance, dependence, and addiction.

InChI:InChI=1/C7H8N2O3/c1-2-3-4-5(10)8-7(12)9-6(4)11/h2,4H,1,3H2,(H2,8,9,10,11,12)

Upstream product

• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 
• 141-52-6 sodium ethanolate 
• 57-13-6 urea 
• 76-73-3 5-Allyl-5-(1-methyl-butyl)-barbitursaeure; Secobarbital 
• 67-52-7 BARBITURIC ACID 
• 106-95-6 allyl bromide 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 

Relevant articles and documents

Dihydropyrrolo[2,3- d ]pyrimidines: Selective Toll-Like Receptor 9 Antagonists from Scaffold Morphing Efforts

Toll-like receptors (TLRs) play important roles in the innate immune system. In fact, recognition of endogenous immune complexes containing self-nucleic acids as pathogen- or damage-associated molecular patterns contributes to certain autoimmune diseases, and inhibition of these recognition signals is expected to have therapeutic value. We identified dihydropyrrolo[2,3-d]pyrimidines as novel selective TLR9 antagonists with high aqueous solubility. A structure-activity relationship study of a known TLR9 antagonist led to the promising compound 18, which showed potent TLR9 antagonistic activity, sufficient aqueous solubility for parenteral formulation, and druggable properties. Compound 18 suppressed the production of the proinflammatory cytokine IL-6 in CpG-induced mouse model. It is therefore believed that compound 18 has great potential in the treatment of TLR9-mediated systemic uncontrollable inflammatory response like sepsis.

N-HYDROXYLAMINO-BARBITURIC ACID DERIVATIVES AS NITROXYL DONORS

The present disclosure provides N-hydroxylamino-barbituric acid compounds of formulae (1)- (4), pharmaceutical compositions and kits comprising them, and methods of using such compounds or pharmaceutical compositions. The present disclosure provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

Syntheses of 7-alkyl-1,3,6-trimethylpyrrolo[2,3-d]pyrimidines and 4-alkylamino-2,5-dimethyl-2,3-dihydrofuro[3,2-e]pyrimidines

7-Alkyl-1,3,6-trimethylpyrrolo[2,3-d]pyrimidine-2,4(1H,3H)-diones were readily synthesized by treatment of 6-alkylamino-5-allyl-1,3-dimethyluracils, which were derived from 5-allyl-6-chloro-1,3-dimethyluracil and alkylamines, with bis(acetonitrile) palladium (II) chloride. In addition, 4-alkylamino-2,5-dimethyl-2,3-dihydrofuro[3,2-e]pyrimidin-6-ones were easily synthesized by treatment of 5-allyl-6-chloro-1-methyluracil with alkylamines.