57270-81-2

Usage

Uses

Used in Pharmaceutical Industry:
5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid is used as a sedative or hypnotic agent for its potential to affect the central nervous system, providing calming or sleep-inducing effects. Its structure suggests it may have therapeutic applications in managing conditions related to anxiety, insomnia, or other disorders that could benefit from its sedative properties.
Used in Research and Development:
In the scientific community, 5-[[4-(dimethylamino)phenyl]methylene]-1,3-dimethylbarbituric acid serves as a subject for research to explore its pharmacological properties, mechanism of action, and potential side effects. This could lead to the development of new drugs or therapies based on its chemical structure and activity.

InChI:InChI=1/C15H17N3O3/c1-16(2)11-7-5-10(6-8-11)9-12-13(19)17(3)15(21)18(4)14(12)20/h5-9H,1-4H3

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 889-37-2 N,N-dimethyl-4-((phenylimino)methyl)aniline 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 24431-17-2 N-(p-dimethylaminobenzylidene)benzylamine 
• 57270-84-5 1,3-dimethyl-5-(4-methyl-benzylidene)-pyrimidine-2,4,6-trione 

Downstream Products

• 1093169-06-2 3-(1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-3-(4-(dimethylamino)phenyl)-2-(4-nitrophenyl)propionitrile 
• 1259377-27-9 4-(6-(4-(dimethylamino)phenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,6-hexahydrofuro[2,3-d]pyrimidin-5-yl)benzonitrile 
• 1341225-24-8 7,9-dimethyl-4-(4-dimethylaminophenyl)-1,3-diphenyl-1,2,7,9-tetraaza-spiro[4.5]dec-2-ene-6,8,10-trione 
• 100-10-7 4-dimethylamino-benzaldehyde 

Relevant academic research and scientific papers

Merocyanine-type dyes from barbituric acid derivatives

The preparation and the solvatochromic behavior of two dyes, obtained by condensation of N,N′-dimethylbarbituric acid with dimethylaminobenzaldehyde and with 4,4′-bis(N,N-dimethylamino)benzophenone (Michler's ketone) are described. The latter dye is rathe

Rational Design of Crystallization-Induced-Emission Probes To Detect Amorphous Protein Aggregation in Live Cells

Unlike amyloid aggregates, amorphous protein aggregates with no defined structures have been challenging to target and detect in a complex cellular milieu. In this study, we rationally designed sensors of amorphous protein aggregation from aggregation-induced-emission probes (AIEgens). Utilizing dicyanoisophorone as a model AIEgen scaffold, we first sensitized the fluorescence of AIEgens to a nonpolar and viscous environment mimicking the interior of amorphous aggregated proteins. We identified a generally applicable moiety (dimethylaminophenylene) for selective binding and fluorescence enhancement. Regulation of the electron-withdrawing groups tuned the emission wavelength while retaining selective detection. Finally, we utilized the optimized probe to systematically image aggregated proteome upon proteostasis network regulation. Overall, we present a rational approach to develop amorphous protein aggregation sensors from AIEgens with controllable sensitivity, spectral coverage, and cellular performance.

Barbituric acid based fluorogens: Synthesis, aggregation-induced emission, and protein fibril detection

Fluorescent dyes, especially those emitting in the long wavelength region, are excellent candidates in the area of bioassay and bioimaging. In this work, we report a series of simple organic fluorescent dyes consisting of electron-donating aniline groups and electron-withdrawing barbituric acid groups. These dyes are very easy to construct while emitting strongly in the red region in their solid state. The photophysical properties of these dyes, such as solvatochromism and aggregation-induced emission, are systematically characterized. Afterward, the structure-property relationships of these barbituric acid based fluorogens are discussed. Finally, we demonstrate their potential applications for protein amyloid fibril detection.

One-Pot Knoevenagel and [4 + 2] Cycloaddition as a Platform for Calliviminones

Bioactive compounds featuring an unusual core of spiro[5.5]undecenes and calliviminones were synthesized in very good yield with good regio- and diastereoselectivities through a one-pot Knoevenagel and [4 + 2] cycloaddition from the readily available aldehydes, cyclic-1,3-diones, dienes, and a catalytic amount of (s)-proline.

Tosylmethylisocyanide (TosMIC) [3+2] cycloaddition reactions: A facile Van Leusen protocol for the synthesis of the new class of spirooxazolines, spiropyrrolines and Chromeno[3,4-c]pyrrols

The reactivity and chemo-, regio- and diastreo-selectivity of tosylmethyl isocyanides (TosMIC) are investigated in Van Leusen type [3 + 2] cycloaddition reactions with the various activate cyclic ketones and double C–C bonds in the synthesis of spirooxazolines, spiropyrrolines and chromeno[3,4-c]pyrrols in good to excellent yields under catalyst-free conditions without any activation at ambient temperature.

Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines

Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.

Structurally simple D–A-type organic sensitizers for dye-sensitized solar cells: effect of anchoring moieties on the cell performance

Abstract: In this work, we report synthesis and device fabrication studies of four metal-free D–A-type dyes (A1–A4) based on structurally simple N,N-dimethyl-4-vinyl aniline carrying four different acceptor/anchoring groups, as sensitizers for sensitizing photoanode (TiO2). In the sensitizers, N,N-dimethylaniline ring acts as an electron donor, while barbituric acid, N,N-dimethyl barbituric acid, thiobarbituric acid and N,N-diethyl thiobarbituric acid function as electron acceptor/anchoring units. They were synthesized in good yield via Knoevenagel protocol in neutral condition without any catalyst. Further, they were subjected to structural, electrochemical and optical characterization in order to evaluate their structure, band gap and absorption/emission behavior. The studies reveal that all the four dyes have thermodynamic feasibility of electron injection as well as electron recombination; their optical band gaps were found to be in the range of 2.35–2.56?eV. High-quality crystals of A2 and A4 were grown by slow evaporation technique using its solution with 1:1 pet ether (60–80?°C)/ethyl acetate solvent mixture at room temperature. Their SC-XRD studies disclose that the crystals are in the triclinic system with space group P-1. Further, DFT studies were performed using Turbomole V7.1 software package to evaluate their optimized geometry and HOMO and LUMO levels. Finally, DSSC device fabricated with the dye A1 showed relatively good efficiency when compared to other dyes mainly due to the effective binding of barbituric acid on the surface of TiO2 through NH or OH functional group. Graphical Abstract: [Figure not available: see fulltext.].

Facile fabrication of AIE/AIEE-active fluorescent nanoparticles based on barbituric for cell imaging applications

Four barbituric derivatives (1-4), were synthesized with obvious aggregation induced emission (AIE) or aggregation induced emission enhancement (AIEE) behaviors. The optical properties in different states and the mechanisms of the enhanced emission of 1-4 were investigated. We found that there were a large number of globular or blocky nanoparticles with average diameters from 229 to 394 nm in tetrahydrofuran (THF)/water solutions when the water fraction (fw) was 90%. The single crystal data of 2 and 4 reveal that multiple intermolecular interactions restrict the intramolecular motions, and promote the formation of a herringbone arrangement (4), thus permitting intense emission in the aggregate state. In addition, the frontier molecular orbital energy and band gap calculated by density functional theory (DFT) are consistent with the experimental results. Compound 4 is cell-permeable: upon entering the live cells, the dye molecules can accumulate in the lysosomes and turn on the fluorescence.

The synthesis and evaluation of near-infrared probes with barbituric acid acceptors for in vivo detection of amyloid plaques

A new array of near-infrared probes containing barbituric acid acceptors has been developed as Aβ imaging agents. These probes displayed long-emission wavelengths and large Stokes shifts, as well as high affinities for Aβ aggregates. In vivo and ex vivo studies demonstrated that BBTOM-3 could intensely label Aβ plaques in the brains of transgenic mice.

Colorimetric detection of fluoride ion by 5-arylidenebarbituric acids: Dual interaction mode for fluoride ion with single receptor

Two 5-arylidenebarbituric acid derivatives (IH and IM) have been synthesized by the Knoevenagel condensation of barbituric acid with 4-N,N-dimethylamino benzaldehyde and studied for anion sensing activities. Both receptors sense fluoride ion with high selectivity and sensitivity and the sensing action has been demonstrated by naked eye detection, UV-visible absorption, and fluorescence spectral changes in the presence of F-. Indeed, the F- sensing mechanism for receptor IH depends on F - ion concentration. While at higher concentrations F- forms strong hydrogen bonding interaction with the N-H proton of the receptor, at lower concentrations sensing is influenced by the deprotonation of the methylene proton, followed by the chemical reaction, which is also confirmed by the 1H-NMR technique. On the other hand, when replacing the N-H proton with a methyl group, IM does not show any concentration dependent behaviour with F-. The F- concentration dependent sensing is attributed to the changes in the receptor-anion interaction equilibrium, where at higher F- concentrations, F- interacts with the receptor through hydrogen bonding and at lower concentrations it induces a chemical reaction.