7391-69-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Isopropylbarbituric acid is used as a medication for the treatment of various conditions such as seizures, insomnia, and anxiety. Its application is based on its ability to induce a calming effect and reduce brain activity, providing relief from the symptoms associated with these conditions.
Used in Medical Treatments:
5-Isopropylbarbituric acid is used as a therapeutic agent for the management of neurological disorders characterized by excessive brain activity or heightened emotional states. The application reason is its effectiveness in enhancing GABA activity, which helps in reducing brain activity and providing a calming effect.

InChI:InChI=1/C7H10N2O3/c1-3(2)4-5(10)8-7(12)9-6(4)11/h3-4H,1-2H3,(H2,8,9,10,11,12)

Upstream product

• 759-36-4 diethyl isopropylmalonate 
• 67-52-7 BARBITURIC ACID 
• 67-64-1 acetone 
• 57-13-6 urea 
• 64-17-5 ethanol 
• 98546-82-8 5-chloro-5-isopropyl-barbituric acid 
• 16952-71-9 5-bromo-5-isopropyl-barbituric acid 
• 75-26-3 isopropyl bromide 
• 105-53-3 diethyl malonate 

Downstream Products

• 1146-21-0 5-FU 
• 545-93-7 5-(2-bromoallyl)-5-isopropylbarbituric acid 
• 77-02-1 aprobarbital 
• 17432-95-0 5-isopropyluracil 
• 41333-98-6 4-(5-isopropyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-N-thiazol-2-yl-benzenesulfonamide 
• 41334-03-6 4-(5-isopropyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-N-(4-methyl-thiazol-2-yl)-benzenesulfonamide 
• 41334-07-0 N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-4-(5-isopropyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-benzenesulfonamide 
• 176519-55-4 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 172256-08-5 6-[(3,5-dimethylphenyl)selenenyl]-1-(ethoxymethyl)-5-isopropyluracil 
• 172256-31-4 1-[(benzyloxy)methyl]-6-chloro-5-isopropyluracil 
• 1780-42-3 2,4,6-trichloro-5-isopropylpyrimidine 

Relevant academic research and scientific papers

NOVEL COMPOUNDS AND THEIR USES AS THYROID HORMONE RECEPTOR AGONISTS

A compound of formula (I) or (Ia), or a tautomer or a pharmaceutically acceptable salt thereof is provided. Compounds of formula (II) to (V), or a tautomer or a pharmaceutically acceptable salt thereof are also provided. These compounds and the pharmaceutical compositions containing them are useful for the treatment of diseases such as obesity, hyperlipidemia, hypercholesterolemia and diabetes and other related disorders and diseases, and may be useful for other diseases such as NASH, atherosclerosis, cardiovascular diseases, hypothyroidism, thyroid cancer and other disorders and diseases related thereto． (I), (Ia)

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.

PROCESSES FOR PREPARING HIV REVERSE TRANSCRIPTASE INHIBITORS

Compounds of Formula (I): can be prepared by a multi-step process from compounds of Formula (II): wherein G is Cl, Br or I.

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.

Method for preparing 5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1h,3h)-dione

The invention relates to a process for the preparation of 5-(1-methylethyl)-6 -(phenylmethyl)pyrimidine-2,4(1H,3H)-dione.

Reductive C-alkylation of barbituric acid derivatives with carbonyl compounds in the presence of platinum and palladium catalysts

Effective synthetic procedures for the preparation of mono- and di-C-alkylated barbituric acid derivatives through palladium and platinum catalytic hydrogenation of solutions of barbituric acids (unsubstituted, N-mono, and N,N′-disubstituted barbituric acids) and carbonyl compounds (aliphatic and aromatic aldehydes and ketones).

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.