5909-46-6

Usage

Uses

Used in Pharmaceutical Industry:
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-[(4-methoxyphenyl)methyl]is used as a potential component for drug development due to its unique structure and potential biological activities. Its presence in the class of pyrimidine derivatives makes it a promising candidate for medicinal chemistry, where it can be further explored and modified to create new therapeutic agents.
Used in Scientific Research:
In addition to its pharmaceutical applications, 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-[(4-methoxyphenyl)methyl]can be utilized in scientific research as a reference compound. Its distinct chemical properties and structure make it valuable for studying various biological processes and interactions.
Used in Chemical Synthesis:
Furthermore, 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-[(4-methoxyphenyl)methyl]- can be employed in chemical synthesis for the production of new compounds. Its unique structure and reactivity can be leveraged to create novel molecules with potential applications in various fields, including materials science, pharmaceuticals, and other industries.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 49546-71-6 5-(4-methoxybenzylidene)barbituric acid 

Relevant academic research and scientific papers

BARBITURIC ACID DERIVATIVES AS SELF-TANNING SUBSTANCES

The present invention relates to the use of barbituric acid derivatives of the formula I as self-tanning substance, for increasing melanin synthesis, for improving melanin transport and/or improving the distribution of melanin in superbasal layers, to preparations comprising these barbituric acid derivatives, and to specific barbituric acid derivatives.

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Barbituric and thiobarbituric acid derivatives have become progressively attractive to medicinal chemists due to their wide range of biological activities. Herein, different series of 1,3,5-trisubstituted barbiturates and thiobarbiturates were prepared in moderate to excellent yields and their activity as xanthine oxidase inhibitors, antioxidants, antibacterial agents and as anti-proliferative compounds was evaluated in vitro. Interesting bioactive barbiturates were found namely, 1,3-dimethyl-5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6c) and 1,3-dimethyl-5-[1-[2-(4-nitrophenyl)hydrazinyl]ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6e), which showed concomitant xanthine oxidase inhibitory effect (IC50 values of 24.3 and 27.9 μM, respectively), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (IC50 values of 18.8 and 23.8 μM, respectively). In addition, 5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6d) also revealed DPPH radical scavenger effect, with an IC50 value of 20.4 μM. Moreover, relevant cytotoxicity against MCF-7 cells (IC50 = 13.3 μM) was observed with 5-[[(2-chloro-4-nitrophenyl)amino]methylene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (7d). Finally, different 5-hydrazinylethylidenepyrimidines revealed antibacterial activity against Acinetobacter baumannii (MIC values between 12.5 and 25.0 μM) which paves the way for developing new treatments for infections caused by this Gram-negative coccobacillus bacterium, known to be an opportunistic pathogen in humans with high relevance in multidrug-resistant nosocomial infections. The most promising bioactive barbiturates were studied in silico with emphasis on compliance with the Lipinski's rule of five as well as several pharmacokinetics and toxicity parameters.

2-Phenyl-2,3-dihydrobenzo[ d ]thiazole: A Mild, Efficient, and Highly Active in situ Generated Chemoselective Reducing Agent for the One-Pot Synthesis of 5-Monoalkylbarbiturates in Water

A metal- and catalyst-free reductive alkylation protocol for the one-pot synthesis of 5-monoalkylbarbiturates from barbituric acids and aldehydes using the in situ generated chemoselective reducing agent 2-phenyl-2,3-dihydrobenzo[ d ]thiazole from 2-aminothiophenol and benzaldehyde is described. The notable advantages of the protocol are operational simplicity, mild reaction conditions, high yield, short reaction time, and simple workup and purification process which make it highly attractive.

Composition for trichogenousness

The present invention relates to novel barbiturate and thiobarbiturate derivatives and a composition for promoting hair growth using the same. According to the present invention, the barbiturate and thiobarbiturate derivatives, in an animal model, have shown to promote hair growth and have excellent effects on hair growth by promoting regulation of Wnt/andbeta;-catenin and hair growth factor signaling and suppressing mechanism of apoptosis. Accordingly, the barbiturate and thiobarbiturate derivatives of the present invention may be used as a composition for promoting hair growth.COPYRIGHT KIPO 2017

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.

Design, synthesis and in vivo evaluation of sodium 2-benzyl-chloromalonates as new central nervous system depressants

This work describes the design, synthesis and in vivo evaluation of new central nervous system depressing agents that show low levels of acute toxicity as well as high solubility in water and exhibit anxiolytic and hypnotic effects. These new compounds are sodium 2-benzyl-2-chloromalonates, which were designed using molecular modelling techniques and synthesized in four steps, with an overall yield between 41% and 65%. In vivo tests with mice, including pentobarbital-induced sleep, rotarod, open field and elevated plus maze tests, were carried out, and the results indicated that some of these agents induce activities similar to those induced by diazepam but with lower hypnotic potency and greater anxiolytic potency. These compounds were also orally administered to mice in doses of 2 g kg-1, and their effects were evaluated for 14 days. The mice did not show signs of intoxication, confirming that sodium 2-benzyl-2-chloromalonates exhibit low levels of acute toxicity. These observations indicate that sodium 2-benzyl-2-chloromalonates and their analogues are efficient and safer central nervous system depressing drugs relative to existing standards of care.

Synthesis and in vivo evaluation of 5-chloro-5-benzobarbiturates as new central nervous system depressants

A new family of barbiturates, 5-chloro-5-benzylbarbituric acids, was prepared using a simple efficient synthetic method from aromatic aldehydes and barbituric acid, followed by reduction and chlorination with trichloro-isocyanuric acid, affording overall yields of 53 to 70percent. The in vivo evaluation with mice showed that these compounds present tranquilizing activity.

Synthesis and antimicrobial activities of novel 5-substituted pyrimidin-2,4,6-triones

5-Benzylpyrimidin-2,4,6-triones (3a-c), 5-((furan-2-yl)methyl)pyrimidin-2, 4,6-trione (3g) and 5-((3-aryl-1-phe-nyl-1H-pyrazol-4-yl)methyl)pyrimidin-2,4,6- triones (3h-j) were obtained in two steps. Reaction of barbituric acid (1) with various substituted aromatic aldehydes, furfuraldehyde and 3-aryl-1-phenyl-1H- pyrazole-4-carbaldehydes in methanol yielded the corresponding chalcones 2a-m in 48-85% yield. These chalcones on reduction with sodium borohydride in isopropyl alcohol furnished desired novel compounds 3a-c and 3g-j in 55-85% yield. The structure of all the synthesized compounds have been established by various spectral studies and elemental analysis. All the synthesized compounds have been screened for antimicrobial activity.

Modified pyrimidine glucocorticoid receptor modulators

The present invention provides a novel class of modified pyrimidine compounds and compositions and methods of using the compounds as glucocorticoid receptor modulators.

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.