2518-72-1

Basic information

• Product Name: 5-ethylbarbituric acid
• Synonyms: 5-ethylbarbituric acid;5-Ethylpyrimidine-2,4,6(1H,3H,5H)-trione;5-ethyl-1,3-diazinane-2,4,6-trione
• CAS NO: 2518-72-1
• Molecular Formula: C₆H₈N₂O₃
• Molecular Weight: 156.13932
• EINECS: 219-743-9
• Mol File: 2518-72-1.mol

Chemical Properties

• Melting Point: 225-226 °C
• Appearance: /
• Density: 1.243 g/cm³
• Refractive Index: 1.467
• PKA: 4.62±0.40(Predicted)
• CAS DataBase Reference: 5-ethylbarbituric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ethylbarbituric acid(2518-72-1)
• EPA Substance Registry System: 5-ethylbarbituric acid(2518-72-1)

Safety Data

• Hazardous Substances Data: 2518-72-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-ethylbarbituric acid is used as a hypnotic and sedative agent for the treatment of insomnia and anxiety disorders. It is utilized for its ability to induce sleep and provide relaxation by enhancing inhibitory neurotransmission in the brain.
Used in Medical Applications:
In the medical field, 5-ethylbarbituric acid is used as a preoperative medication to induce sedation and reduce anxiety in patients prior to surgery. Its effects on the central nervous system make it suitable for this purpose.
Used in Controlled Substances Regulation:
Due to its potential for abuse and addiction, 5-ethylbarbituric acid is used in the context of controlled substances regulation to ensure that its distribution and use are monitored and limited to prevent misuse. This regulatory use aims to protect public health and safety by minimizing the risks associated with barbiturate abuse.

InChI:InChI=1/C6H8N2O3/c1-2-3-4(9)7-6(11)8-5(3)10/h3H,2H2,1H3,(H2,7,8,9,10,11)

Upstream product

• 58713-02-3 5-acetyl-pyrimidine-2,4,6-trione 
• 67-52-7 BARBITURIC ACID 
• 64-17-5 ethanol 
• 75-07-0 acetaldehyde 
• 5750-82-3 5-bromo-5-ethyl-pyrimidine-2,4,6-trione 
• 5750-81-2 5-chloro-5-ethyl-pyrimidine-2,4,6-trione 
• 7664-93-9 sulfuric acid 
• 76-74-4 pentobarbital 
• 10035-10-6 hydrogen bromide 
• 75016-38-5 vinbarbital 
• 76-76-6 probarbital 
• 7647-01-0 hydrogenchloride 
• 24867-19-4 5-ethyl-pyrimidine-2,4,6-triamine 
• 6082-49-1 ethyl propanediamide 

Downstream Products

• 15302-82-6 5-Aethyl-5-(β-hydroxy-β-phenylaethyl)-barbitursaeure 
• 1310053-25-8 6-[4-(2-methoxyphenyl)-1-piperazinyl]-5-ethyluracil 
• 1310053-24-7 6-(4-phenyl-1-piperazinyl)-5-ethyluracil 
• 854840-82-7 5-ethyl-5-(5-hydroxymethyl-2-methyl-5-nitro-[1,3]dioxan-2-ylmethyl)-barbituric acid 
• 4212-49-1 5-ethyluracil 
• 172256-32-5 1-Benzyloxymethyl-6-chloro-5-ethyl-1H-pyrimidine-2,4-dione 
• 172256-05-2 1-[(benzyloxy)methyl]-6-[(3,5-dimethylphenyl)selenenyl]-5-ethyluracil 
• 172256-02-9 6-(3,5-Dimethyl-phenylselanyl)-1-ethoxymethyl-5-ethyl-1H-pyrimidine-2,4-dione 
• 155831-53-1 1-<(benzyloxy)methyl>-5-ethyl-6-(phenylselenenyl)uracil 
• 171048-61-6 5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 
• 152433-65-3 6-phenylthio-5-ethyuracil 
• 564456-35-5 methyl (5-ethyl-2,4,6-trioxo-hexahydropyrimidin-5-yl)acetate 
• 1780-38-7 2,4,6-trichloro-5-ethylpyrimidine 
• 57-44-3 diethylbarbituric acid 

Relevant articles and documents

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.

Synthesis and antimicrobial activity of some novel 5-alkyl-6-substituted uracils and related derivatives

6-Chloro-5-ethyl-, n-propyl- and isopropyluracils 5a-c were efficiently prepared from the corresponding 5-alkybarbituric acids 3a-c via treatment with phosphorus oxychloride and N,N-dimethylaniline to yield the corresponding 5-alkyl-2,4,6-trichloropyrimidines 4a-c, which were selectively hydrolyzed by heating in 10% aqueous sodium hydroxide for 30 minutes. The reaction of compounds 5a-c with 1-substituted piperazines yielded the corresponding 5-alkyl-6-(4-substituted-1-piperazinyl)uracils 6a-j. The target 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-diones 7a-c were prepared via the reaction of 5a-c with sodium azide. Compounds 6a-j and 7a-c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 6h displayed potent broad-spectrum antibacterial activity, while compound 6b showed moderate activity against the Gram-positive bacteria. All the tested compounds were practically inactive against Candida albicans.

6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase

N-3-Hydroxylation of pyrimidine-2,4-diones was recently found to yield inhibitors of both HIV-1 reverse transcriptase (RT) and integrase (IN). An extended series of analogues featuring a benzoyl group at the C-6 position of the pyrimidine ring was synthesized. Through biochemical studies it was found that these new analogues are dually active against both RT and IN in low micromolar range. Antiviral assays confirmed that these new inhibitors are active against HIV-1 in cell culture at nanomolar to low micromolar range, further validating 3-hydroxypyrimidine-2,4-diones as a viable scaffold for antiviral development.

Non-nucleoside HIV-1 reverse transcriptase inhibitors, part 7. Synthesis, antiviral activity, and 3D-QSAR investigations of novel 6-(1-naphthoyl) HEPT analogues

A series of novel 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) analogues bearing a 6-(1-naphthoyl) group of non-nucleoside human immunodeficiency virus (HIV) reverse transcriptase inhibitors were synthesized and evaluated for their activity against HIV-1 and HIV-2. It was found that most of these compounds showed good activity against HIV-1. Among them, compound 5-isopropyl-6-(1-naphthoyl)-1-[(2E)-3-phenylallyl]-2,4-pyrimidinedione (23) displayed the greatest inhibitory potency (IC50=0.14 μM), which is about 35-fold more active than HEPT and DDI. To rationalize the relationships between structure and activity of these novel compounds, a three-dimensional quantitative structure-activity relationship (3D-QSAR) model was also generated. The results provided a tool for guiding the further design of more potent antiviral agents and for predicting the affinity of related compounds.

Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates

Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.

Barbituric acids as carbon acids. Acidity relationships and 1H and 2H transfer in 1,3-dimethyl-5-tert-butyl- and 5-tert-butylbarbituric acids

Slow ionization and reprotonation at the C5 carbon atom has been observed for 1,3-dimethyl-5-tert-butyl- (1,3-Me2-5-t-Bu), 5-tert-butyl- (5-t-Bu), 1,3-diisopropyl-(1,3-iPr2), and 1,5-diisopropyl- (1,5-i-Pr2) barbituric acids (BA) in aqueous solution at 25.0 deg C and I = 0.1 mol/dm3 (NaCl).For 1,3-Me2-5-t-Bu(BA) (pK = 9.41) deprotonation follows the rate law kf = k1H2O + k1OH-> with k1H2O = 4.0E-4/s, k1OH = 192 dm3/mol.s and reprotonation the rate law kr = k-1H2O + k-1H+> with k-1H2O = 8.9E-3/s, k-1H = 1.12E6 dm3/mol.s (pH range 6.91-12.89).For the 2H(C5) derivative the corresponding dedeuteration rates are k1H2O = 7.7E5/s (kH/kD = 5.5) and K1OH = 54 dm3/mol.s (kH/kD = 3.5).Deprotonation is catalysed by general bases (kB dm3/mol.s, kH/kD), 2,6-lutidine (0.0108, 10.0), dabco (29.6, 5.5), NH3 (1.06, 7.1), EtNH2 (14.7, 5.8), Et2NH (18.0,7.2), Et3N(1.30,7.2), but a linear correlation with pKBH is not observed, and structural effects appear to play an important role.The measurement of precise primary kinetic isotope ratios (kH/kd) in water is discussed.In 5-t-Bu(BA)(KH3) ionization at C5 (pK = 8.09+/-0.12) to produce the enolate anion (EH2-) comes into competition with ionization at imide nitrogen (pK = 7.88 +/- 0.04) to produce the keto monoanion (KH2-).In strongly alkaline solution the species deprotonated at both imide nitrogen centers (KH2- is preferred by about 20:1 over the enolate dianion (EH2-)) (C5, and imide nitrogen deprotonated).Such ionizations complicate a study of proton exchange at C5 but this has been clarified by use of the 2H(C5) substituted acid (KDH2)).Deprotonation at C5 occurs via pH independent (k1H2O = 2.59E-3/s, kH/D = 8.1) and OH(1-) dependent (k1OH = 800 dm3/mol.s, kH/kD = 3.4) reactions and via the OH(1-) dependent reactions of KH2(1-) (k2OH = 0.54 dm3/mol.s).Coresspondigly, pathways for reprotonation of the enolate anions are available through the H(1+) dependent (k-1H = 3.2E5 dm3/mol.s) and pH independent (k-1H2O = 1.62E-3/s) reactions of EH1- and through the pH independent reaction of EH(2-) (k-2H2O ca. 0.4/s).The known rates of C5 deprotonation (k1H2O) and reprotonation (k-1H) for barbituric acids have been correlated with carbon acidity (Kc) via linear Broenstead relationships of slope 0.80 and 0.20, respectively (pKc range 2.2-9.6).Barbituric acid carbon acidity is thus demonstrated to be controlled largely by substituent effects on the deprotonation reaction.

Photochemical degradation of barbituric acid derivatives. Part 2: Kinetics of pentobarbital photolysis

The photodegradation of pentobarbital in aqueous solution at different pH values was studied. The spectral changes and calculation of several rate constants lead to the postulation of a model for photodegradation where two processes play an important role, i.e. dealkylation of the secondary substituent at C-5 and the ring opening of the barbiturate. The ratio of these two reactions is in favor of the former process.