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There is an increasing demand for the development of catalytic reagents that are nontoxic due to the growing environmental concerns in the present organic transformation. Bismuth(III) compounds have significant potential as catalysts for a range of organic synthesis due to their low toxicity, strong Lewis acid catalytic activity, and great flexibility. In this research work, a series of various chemically and pharmacologically important six‐membered fused nitrogen‐/oxygen‐based heterocycle derivatives were efficiently prepared via a one‐pot multicomponent reaction starting from aromatic aldehydes, malononitrile, and barbituric acid in presence of green and reusable Lewis catalyst bismuth(III) triflate, that is, Bi(OTf)3 in EtOH/H2O (1:1) media. Bi(OTf)3 has the additional benefit of being reusable catalyst, ready availability, eco‐friendliness, and easy to handle to obtain corresponding products in excellent yields (83%–94%). Structure of all synthesized products was characterized on the basis of FT‐IR, 1H‐NMR, 13C‐NMR, and ESI–MS analysis. [ABSTRACT FROM AUTHOR]

Objective: To synthesize bis-Schiff bases bearing thiobarbituric acid and to screen their anti-urease inhibitory potential. Methods: In this study, 1,3-dimethylbarbituric acid derivatives were synthesized by a four-step process. Using K2CO3, 2,4-dihydroxy benzaldehyde and chloro ethyl acetate were esterified in DMF in the first step under reflux condition. The reaction was then carried out by combining the esterified aldehyde with 1,3-dimethylbarbituric acid at room temperature for about an 1 h. Hydrazine hydrate was then mixed with compound (II) in ethanol solvent with acetic acid acting as catalyst. Finally, substituted aromatic aldehydes were treated with bis-hydrazide (III) using ethanol and acetic acid as a catalyst. Results: The newly synthesized compounds were screened for their urease inhibition (in vitro). Four analogs, including (IIIj) (IC50 = 15.22 ± 0.49 μM), (IIIg) (IC50 = 16.05 ± 0.16 μM), (IIIa) (IC50 = 16.29 ± 0.73 μM), and (IIIb) (IC50 = 21.17 ± 0.21 μM) were found most powerful inhibitors than standard thiourea (IC50 = 22.80 ± 2.20 μM). The urease inhibition was also seen in compound (IIIi), (IIIc), (IIIh), (IIIe), (IIId), and (IIIf) however it was less from standard. The structure stability and chemical reactivity of the compounds were checked by density functional theory (DFT) method. Furthermore, the molecular docking simulation was performed to check the protein (urease) and ligand interactions and binding affinities by using AutoDock Vina. Conclusions: The synthesized derivatives attributed temendous potential against urease enzyme. Compound (IIIj) was found as the most potent anti-urease agent. Additional research including taxicological and in vivo is necessary to know the safety, effectivness and mechanism of action of these potent molecules. [ABSTRACT FROM AUTHOR]

Barbituric acid is a heterocyclic compound with various pharmacological and biological applications. This review paper provides a comprehensive overview of barbituric acid’s synthesis, reactions, and bio-applications, highlighting its multifaceted role in various fields. Many heterocyclic derivatives were formed based on barbituric acid, for instance, pyrano-fused pyrimidine derivatives, spiro-oxindole derivatives, chrome-based barbituric acid derivatives, and many more via the atom economic method, Michael addition reaction, Knoevenagel condensation reaction, etc. In the context of bio-applications, this review examines the production of a wide range of bioactive drugs like anti-histamine, anti-leprotic, sedative–hypnotic, anti-inflammatory, anti-urease, antiviral, anti-AIDS, antimicrobial, antioxidant, anticonvulsant, anesthetic agent, antitumor, and anticancer drugs using efficient multicomponent reactions. By showcasing the versatility and potential of this compound, it aims to inspire further research and innovation in the field, leading to the development of novel barbituric acid derivatives with enhanced properties and diverse applications, with coverage of the literature relevant up to 2024.

Owing to the carcinogenicity and environmental risks as well as the wide industrial use of hydrazine, we report herein a colorimetric probe for its ratiometric detection in pure water. The developed probe possesses push‐pull architecture with 2‐(piperidyn‐1‐yl) thiophene as the donor, N,N’‐dibutylbarbituric as the acceptor, and butadiene as the spacer. In contrast to weak solvatochromic behavior in organic solvents, the probe showed distinct optical photophysical properties in water resulting from the formation of nanoscopic aggregates. The probe underwent pronounced spectral changes upon the addition of hydrazine including an 11.5‐fold decrease in absorbance and ~2.4‐fold fluorescence quenching. The mechanistic investigation revealed the rapid formation of hydrazone upon the interaction of the probe with hydrazine via retro‐Knoevenagel reaction as confirmed experimentally and corroborated with DFT calculations. The induced colorimetric and fluorometric changes were utilized in hydrazine sensing with excellent selectivity over other biologically relevant analytes with a detection limit of 0.76 μM in aqueous media. The practical utility of the probe was assessed in real‐life natural water samples, while we have also developed a cost‐effective portable kit for the on‐site hydrazine detection both in the solution and vapor phases. [ABSTRACT FROM AUTHOR]

Barbituric acid is a heterocyclic compound with various pharmacological and biological applications. This review paper provides a comprehensive overview of barbituric acid's synthesis, reactions, and bio-applications, highlighting its multifaceted role in various fields. Many heterocyclic derivatives were formed based on barbituric acid, for instance, pyrano-fused pyrimidine derivatives, spiro-oxindole derivatives, chrome-based barbituric acid derivatives, and many more via the atom economic method, Michael addition reaction, Knoevenagel condensation reaction, etc. In the context of bio-applications, this review examines the production of a wide range of bioactive drugs like anti-histamine, anti-leprotic, sedative–hypnotic, anti-inflammatory, anti-urease, antiviral, anti-AIDS, antimicrobial, antioxidant, anticonvulsant, anesthetic agent, antitumor, and anticancer drugs using efficient multicomponent reactions. By showcasing the versatility and potential of this compound, it aims to inspire further research and innovation in the field, leading to the development of novel barbituric acid derivatives with enhanced properties and diverse applications, with coverage of the literature relevant up to 2024. [ABSTRACT FROM AUTHOR]

Supramolecular polymers are polymeric materials of monomeric fragments, held jointly by reversible and directional non-covalent interactions such as multiple hydrogen-bonding, charge transfer effects, host–guest interactions, metal coordination, and aromatic stacking. This review article on the Hamilton-based supramolecular polymers aims to shed light on the molecular recognition achievements by the Hamilton-based polymeric systems, evaluate Hamilton receptor's future prospects, and capitalize its potential applications in supramolecular chemistry. To the best of our knowledge, this is the first elaborative and sole manuscript in which polymeric Hamilton receptors are being exposed in detail. The first portion of this manuscript is related to the importance and urgency of polymers along with the historic background of Hamilton receptors. The middle section discloses the potential applications of Hamilton-type receptors in various fields, e.g., dendrimers, mechanically polymeric rotaxanes, and self-assemblies. The final section of the manuscript discloses the future aspects and the importance of novel polymer-based Hamilton-type receptors in the modern era. We believe that this first review in this emerging yet immature field will be useful to inspire scientists around the world to find the unseen future prospects, thereby boosting the field related to this valued artificial receptor in the province of supramolecular chemistry and also in other domains of scientific fields and technology, as well. [ABSTRACT FROM AUTHOR]

Two novel metal complexes, C1 and C2, were synthesized through the reaction of an azo dye ligand, obtained by coupling 4‐chloroaniline with 1,3‐dimethyl barbituric acid. The structure of the ligand was confirmed using Fourier‐transform infrared spectroscopy (FTIR) and Nuclear magnetic resonance (NMR). UV–Vis spectroscopy was employed to assess the ligand's sensing ability toward six different metal ions. Comprehensive characterization of the synthesized metal complexes was conducted using elemental analysis, X‐ray photoelectron spectroscopy (XPS), thermogravimetric analysis–difference thermogravimetry (TGA‐DTG), FTIR, UV–Vis spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, and single‐crystal X‐ray diffraction (SC‐XRD). X‐ray analysis revealed octahedral coordination geometry with a 2:1 ligand‐to‐metal ratio and dimethylformamide (DMF) coordination with the metal atom in both complexes. Hirshfeld analysis and 2D fingerprint plots were employed to investigate supramolecular and intermolecular interactions within the crystal system. Density functional theory (DFT/B3LYP) calculations were utilized to compute energy gaps and other important theoretical features. Sensing experiments with tetrabutylammonium fluoride (TBAF) were conducted at a concentration of 1 × 10−5 M. Furthermore, the bioactivity of the synthesized metal complexes and ligand L was evaluated through molecular docking studies against Protein Data Bank (PDB IDs) 4XUY (Staphylococcus aureus) and 3BQW (Aspergillus niger). Also, antimicrobial activity was assessed using the agar well diffusion technique, revealing that complexes C1 and C2 exhibited enhanced antimicrobial activities against the tested organisms compared to the parent azo dye ligand. The computational and experimental bioactivity data are in good agreement with each other. [ABSTRACT FROM AUTHOR]

[Display omitted] The new type of four-component tandem Knoevenagel–Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings. [ABSTRACT FROM AUTHOR]

An effective protocol for synthesis of some new pyrazolylbarbiturate derivatives is reported through a one-pot, three-component reaction between barbituric/thiobarbituric acid, aroylphenylhydrazones and arylglyoxal derivatives. All reactions were conducted in ethanol as solvent without using any catalyst and products were obtained by simple filtering of the precipitated solids in high yields. All products were characterized by 1H and 13C NMR and IR spectral and elemental analysis data. [ABSTRACT FROM AUTHOR]

A method was proposed for the synthesis of some new molecular hybrids containing quinoline, 1,2,3-triazole and barbituric acid residues via Knoevenagel condensation, O-prorgylation and copper(I)-catalyzed azide alkyne cycloaddition reactions. The fourteen compounds were screened for the anticancer activity against MCF-7, MDA-MB-468 and MDA-MB-231 cell lines using MTT assay. Some compounds were screened for inhibitory activity against tyrosine kinase EGFR. Finally, in silico studies like molecular docking on EGFR and VEGFR-2 and ADMET have supported the in vitro results. [ABSTRACT FROM AUTHOR]

A systematic study has been conducted on barbiturate complexes of all five alkali metals, Li–Cs, prepared from metal carbonates or hydroxides in an aqueous solution without other potential ligands present, varying the stoichiometric ratio of metal ion to barbituric acid (BAH). Eight polymeric coordination compounds (two each for Na, K, and Rb and one each for Li and Cs) have been characterised by single-crystal X-ray diffraction. All contain some combination of barbiturate anion BA− (necessarily in a 1:1 ratio with the metal cation M+), barbituric acid, and water. All organic species and water molecules are coordinated to the metal centres via oxygen atoms as either terminal or bridging ligands. Coordination numbers range from 4 (for the Li complex) to 8 (for the Cs complex). Extensive hydrogen bonding plays a significant role in all the crystal structures, almost all of which include pairs of N–H···O hydrogen bonds linking BA− and/or BAH components into ribbons extending in one dimension. Factors influencing the structure adopted by each compound include cation size and reaction stoichiometry as well as hydrogen bonding. [ABSTRACT FROM AUTHOR]

A series of 2‐ and 3‐methylindole (MI)‐based barbituric acid (BA) and thiobarbituric acid (TBA) derivatives (2MIBA, 2MITBA, 3MIBA and 3MITBA) in Donor (D)‐π‐Acceptor (A) configuration having strong intramolecular charge transfer (ICT) interactions were synthesized by the simple and efficient route. Methyl substituent at the 2‐ and 3‐ position alters the coplanarity of the DA systems leaving 2MI derivatives as nonplanar whilst 3MI derivatives as planar one and the latter forms an intramolecular hydrogen bond between indole N−H and −C=O of BA or TBA, which facilitates the excited state intramolecular proton transfer (ESIPT) emission in 3MIBA and 3MITBA. Comparing the UV‐visible absorption spectra in the solution phase reveals that the ICT band of 2MITBA and 3MITBA are red‐shifted from the 2MIBA and 3MIBA due to the stronger electron‐accepting nature of C=S than the C=O. Since these molecules exert photo‐induced intramolecular charge transfer followed by a rotation around the bridging methylene group, only weak fluorescence is noted. Nevertheless, in an aggregated state, both 3MIBA and 3MITBA exhibit significant aggregation‐induced enhanced emission (AIEE) characteristics in their THF/water mixture, but the effect is not promising for 2MIBA and 2MITBA. Further, melamine‐3MITBA co‐assembly aided through an intermolecular hydrogen bonding network can also be used as a solid‐state emitter. [ABSTRACT FROM AUTHOR]

Hot‐water‐soluble starch (HWSS) was employed as binder for fabrication of a composite from magnetite and Ag nanoparticles (NPs). Electron microscopy images showed a good dispersion of magnetite NPs in the matrix of HWSS. This observation indicates that HWSS tends to coat the maximum surface of magnetite by encapsulation of individual magnetite NPs, leading to disassembly of their aggregates. The HWSS‐coated magnetite NPs were employed as nano‐support for immobilization of fine Ag NPs generated in situ via reduction of Ag+ cations by glucose. Monitoring of the formation and growth of Ag NPs by UV–Vis spectroscopy made it possible to set up an optimal condition for fabrication of the nano‐composite and to verify the supremacy of HWSS‐coated magnetite NPs over bare magnetite NPs as support in this new protocol. Valuable insights into the texture of the nano‐composite were obtained by VSM, FT‐IR and XRD studies. The bio‐derived nano‐composite displayed an interesting magnetic property and an efficient catalytic activity in the three‐component synthesis of pyrano[2,3‐d]pyrimidines. It is a robust heterogeneous catalyst and can be simply retrieved from reaction mixtures by magnetic separation method. [ABSTRACT FROM AUTHOR]

The study focuses on the synthesis of isatin- barbituric acid compounds through a two-step process. In the first step, using mannich reaction, new derivatives of Isatin are synthesized by reacting Isatin with either barbituric acid, along with formaldehyde. This reaction results in the formation of Isatin-barbituric acid derivative. In the second step, these Isatin derivatives are further reacted with various aniline derivatives to generate new compounds containing Isatin. Spectroscopic methods including FTIR, ¹H NMR, and 13C NMR are used to characterize the produced molecules. The study investigates the biological effects of several of the synthetic chemicals on certain bacterial strains, including Klebsiella pneumoniae and Staphylococcus aureus. The potential antibacterial activities of these substances are evaluated. [ABSTRACT FROM AUTHOR]

Insolubility of functional molecules caused by polymorphism sometimes poses limitations for their solution‐based processing. Such a situation can also occur in the preparation processes of supramolecular polymers formed in a solution. An effective strategy to address this issue is to prepare amorphous solid states by introducing a "coformer" molecule capable of inhibiting the formation of an insoluble polymorph through co‐aggregation. Herein, inspired by the coformer approach, we demonstrated a solubility enhancement of a barbiturate π‐conjugated compound that can supramolecularly polymerize through six‐membered hydrogen‐bonded rosettes. Our newly synthesized supramolecular coformer molecule features a sterically demanding methyl group in the π‐conjugated unit of the parent molecule. Although the parent molecule exhibits low solubility in nonpolar solvents due to the formation of a crystalline polymorph comprising a tape‐like hydrogen‐bonded array prior to the supramolecular polymerization, mixing with the coformer compound enhanced the solubility by inhibiting mesoscopic organization of the tapes. The two monomers were then co‐polymerized into desired helicoidal supramolecular polymers through the formation of heteromeric rosettes. [ABSTRACT FROM AUTHOR]

In this paper, two polymers (P-AMB and P-DMAB) with aggregate induced emission (AIE) effect were synthesized successfully. Compared with the polymer monomer BNEA, P-AMB and P-DMAB not only have stronger AIE effect, but also have excellent water solubility and better light stability. In addition, the two polymers were tested for their response to different anions in aqueous solution, and both showed high selectivity and sensitivity to S2−. The sensing mechanism of S2− was studied by ultraviolet visible spectrum, infrared spectrum and 1H NMR spectrum studies. These two polymer sensors have strong anti-interference ability and wide pH response range (5.0 ~ 10.0) when detecting S2−, and could be used for qualitative and quantitative detection of S2− in 100% aqueous solution. [ABSTRACT FROM AUTHOR]

The four-component condensation of ethyl acetoacetate, phenylglyoxal hydrate, barbituric acid, and primary amines was used to obtain polysubstituted pyrroles containing a barbituric acid fragment. In some cases, by-products formed by the three-component condensation of phenylglyoxal hydrate, barbituric acid, and amines were isolated. [ABSTRACT FROM AUTHOR]

A one pot three component reaction of acenaphthoquinone, barbituric acid/thiobarbituric acid/N,N-dimethyl barbituric acid and arylamines in ethanol for the synthesis of acenaphthoindolopyrimidine derivatives is reported. The reactions take place without a catalyst and gentle conditions. This method is facile and has some benefits such as, readily available starting materials, green solvent, catalyst-free, no column chromatographic purification and good to high yields. [ABSTRACT FROM AUTHOR]

An efficient method for the synthesis of functionalized acenaphtho[1,2-b]indol-6b-ol derivatives were developed by the three-component reaction of acenaphthoquinone, barbituric acid, or N, N-dimethyl barbituric acid and aryl amines through sequential Knoevenagel / Michael / intramolecular N-cyclization sequences in ethanol. The reactions were carried out under catalyst-free and mild conditions. Advantages of this method include simple operation, catalyst-free, readily available starting materials, no need to column chromatography purification, and good to high yields (78 - 92 %). We confirmed the product by Fourier-transform infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), and Mass spectrometry.

Fabrication of fluorescent water‐soluble citric acid‐urea based carbon dots have been done using an organic pioneer possessing barbituric acid for the recognition of adenosine triphosphate (ATP). The carbon dots has been characterized through various techniques, such as, powder X‐ray diffraction (PXRD), Fourier‐transform infrared spectroscopy (FTIR), high‐resolution transmission electron microscopy (HRTEM), UV‐visible (UV‐vis), and Fluorescence (FL) spectroscopy. The emissive nature of carbon dots made them worthwhile for the detection of ATP in different plant samples, for instance, curry leaves, coriander, tulsi and jasmine flower leaves. Also, the barbituric acid precursor (1) has been successfully applied for the detection of bisulfate anion in real samples with good recovery. The absorption responses for bisulfate ion permitted it to be used as effective colorimetric sensor in water and the color changes have been scrutinized using smartphone application. [ABSTRACT FROM AUTHOR]

When derivatives of barbituric acid, tetra aromatic aldehyde bearing ether groups and malononitrile or Meldrum acid have one-pot three-component reactions, the analogous new poly pyranopyrimidine derivatives are formed as poly heterocyclic compounds. Deduction of the structures of the products was performed using their IR, 1H-NMR, and 13C-NMR spectroscopy along with CHN analysis. Besides, the synthesized heterocycles were also evaluated concerning their biological activities, including toxicity examination, anti-inflammatory effects, antioxidant activities, and anti-bacterial effects. [ABSTRACT FROM AUTHOR]

Many pathogenic organisms have developed resistance to many antibiotics, which leads to an increase in the spread of many microbial infections. There is an urgent need to find more effective drugs to curb widespread transmission. Hence, this study synthesized and evaluated the antimicrobial activities of mixed-ligand complexes of Cu(II), Co(II), Ni(II), Mn(II), and Zn(II) ions with barbituric acid and 1,10 phenanthroline ligands in effort to find more effective antibiotics. The complexes were characterized using elemental analysis, metal analysis, melting points, solubility tests, and spectroscopic analyses (IR and UV-visible). The antimicrobial activities of the complexes were evaluated against two gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus), two gram-negative bacteria (Pseudomonas aeruginosa and Clostridium spp.), and four pathogenic fungi (Candida albicans, Aspergillus flavus, Aspergillus niger, and Saccharomyces cerevisiae). The biological activities of the metal complexes were compared to the activities of some conventional antibiotics. The molecular formulas for the complexes in 1:1:1 (L-M-L) were established based on the results of the elemental and metal analyses. The IR spectroscopic data results showed the coordination of 1,10-phenanthroline to the metal ions through the nitrogen donor atom, while barbituric acid coordinated with the metal ions through nitrogen and oxygen atoms. The formation of the complexes was confirmed by UV-visible spectroscopic data. Many of the mixed-ligand metal complexes demonstrated higher biological activities than the standard drugs and also succeeded where the conventional antibiotics failed. Therefore, the metal complexes could be considered as more efficacious antibiotics that could be added to the arsenal of effective antibiotics for the prevention of the intrinsic problems of multidrug resistance. [ABSTRACT FROM AUTHOR]

A systematic study has been conducted on barbiturate complexes of all five alkali metals, Li–Cs, prepared from metal carbonates or hydroxides in an aqueous solution without other potential ligands present, varying the stoichiometric ratio of metal ion to barbituric acid (BAH). Eight polymeric coordination compounds (two each for Na, K, and Rb and one each for Li and Cs) have been characterised by single-crystal X-ray diffraction. All contain some combination of barbiturate anion BA− (necessarily in a 1:1 ratio with the metal cation M+), barbituric acid, and water. All organic species and water molecules are coordinated to the metal centres via oxygen atoms as either terminal or bridging ligands. Coordination numbers range from 4 (for the Li complex) to 8 (for the Cs complex). Extensive hydrogen bonding plays a significant role in all the crystal structures, almost all of which include pairs of N–H···O hydrogen bonds linking BA− and/or BAH components into ribbons extending in one dimension. Factors influencing the structure adopted by each compound include cation size and reaction stoichiometry as well as hydrogen bonding.

In this study, natural surface-modified nano-clinoptilolite, NCP@SiO3Pr(CH2)6N4, was synthesized and fully characterized using various analytical techniques, including FT-IR, XRD, SEM, EDS, TEM, and TG-DTA analyses. Additionally, this aminated nanocatalyst was evaluated for the effective synthesis of α,β-unsaturated carbonyl compounds containing valuable substances such as barbituric acid moiety under solvent-free conditions. This catalyst obtained desired products with excellent yields, high purity, and short reaction times. Furthermore, the synthetic, non-toxic heterogeneous nanocatalyst is easily recycled and can be reused several times.

New hydrazone derivate, (1Z,2E)-2-(2-(1-(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)ethyl)hydrazineylidene)-2-(p-tolyl)acetaldehyde oxime (H2L) was synthesized by 5-acetyl-1,3-dimethyl-barbituric acid and p-methyl isonitrosophenylhydrazine. Its molecular and crystal structures were determined by single crystal X-ray analysis. It belongs to triclinic system P-1 space group with a = 7.1722 (3) Å, b = 10.5362 (4) Å, c = 11.7675 (5) Å, α = 98.844 (4)°, β = 98.882 (4)°, γ = 104.330 (4)°, Z = 2 and V = 833.95 (6) Å3. In the molecular structure, the intramolecular N–H···O and N–H···N hydrogen bonds enclose S(6) ring motifs. In the crystal structure, the intermolecular C–H···O and O–H···O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R22(10) and R44(10) ring motifs, in which they may be effective in stabilization of the structure. The Hirshfeld surface analysis of crystal structure indicates that the most important contributions for crystal packing are from H...H (48.5%), H...O/O...H (23.7%) and H...C/C...H (9.7%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in crystal packing. Computational chemistry indicates that in the crystal, O–H···O and C–H···O hydrogen bond energies are 95.9 and 87.5 kJ mol−1. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that stabilization is dominated via the nearly equal strengths of the electrostatic and dispersion energy contributions. [ABSTRACT FROM AUTHOR]

A highly efficient, fast, catalyst‐free, and atom economical method was developed for the synthesis of 5‐benzylidenebarbiturates. Thus, reacting barbituric acid and aldehydes in water as a green solvent under electrochemical conditions afforded the synthesis of the target compounds in six minutes and in highly pure forms. The effects of solvent, reaction time, temperature, electrolyte, and electrode material were studied to optimize the reaction conditions. The scope of the reaction was broadened by the synthesis of 5‐(arylidene)barbiturate derivatives 3 a–3 q using different aldehydes. Calculation of the green chemistry metrics proved the efficiency of the reaction in terms of E‐factor, mass intensity, mass productivity, and reaction mass efficiency. Compound 3 g [5‐(4‐(dimethylamino)benzylidene) barbiturate] was used for the colorimetric detection of cyanide ion over dynamic linear range 1–25 μM with limit of detection (LOD) of 0.86 μM. [ABSTRACT FROM AUTHOR]

One-pot three-component reactions of tetra aromatic aldehyde, including ether groups, derivatives of barbituric acid with ammonia, and ammonium acetate, result in new poly barbituric moiety and, correspondingly, tetra pyrimidodipyrimidine heterocycles. IR, 1H-NMR, and 13C-NMR spectroscopy along with CHN analyses were used to derive the structures of the products. Moreover, the synthesized compounds were investigated in terms of biological performance, consisting of toxicity examination, along with antioxidant, anti-inflammatory, and antibacterial activities. [ABSTRACT FROM AUTHOR]

Complexation in systems containing iron(III) chloride and barbituric (H2BA) or 2-thiobarbituric (H2TBA) acid has been studied by spectrophotometry and pH-metry in the pH range of 1.3–3.3 (I = 0.1 (NaCl), t = 20°C). The presence of 1 : 1 complexes with mono- and deprotonated forms of the ligand has been established, and their stability constants (in log units) have been determined: 1[FeHBA]2+ (3.49 ± 0.15), [FeHTBA]2+ (2.69 ± 0.07), [FeBA]+ (12.22 ± 0.13), and [FeTBA]+ (11.05 ± 0.08). It has been shown that the higher thermodynamic stability of barbiturate complexes compared to 2-thiobarbiturate ones is due to the greater basicity of the barbiturate anion. Based on the stability constants obtained, it has been proposed to use orthophosphate, fluoride, and ethylenediaminetetraacetate ions to eliminate the interfering effect of iron(III) in the determination of malondialdehyde by the thiobarbiturate method. Orthophosphoric acid is the most convenient for practical applications, as it makes it possible to mask iron(III) and to create a strongly acidic medium necessary for the formation of a colored malondialdehyde–H2TBA adduct. [ABSTRACT FROM AUTHOR]

• The new aggregation induced emission (AIE) molecule (BNOH) was synthesized. • The relationship between the molecular structure and appearance of AIE was studied. • The effect of BNOH intermolecular hydrogen bond on molecular AIE was studied. • The formation mode of BNOH molecular aggregates was studied and determined. Barbiturates had been widely studied as a molecule with aggregation induced emission (AIE) phenomenon, but barbiturates as a group with multiple hydrogen bond donor and acceptor sites, the relationship between intermolecular hydrogen bond and AIE phenomenon has not been mainly studied. In this paper, a new barbiturate fluorescence molecule BNOH with hydroxyl group was designed and synthesized in order to analyze the relationship between hydrogen bond and molecular AIE phenomenon by increasing the functional group (–OH) that was easy to form hydrogen bond. By spectroscopic analysis, BNOH had structural torsion in aqueous mixed solution, which led to fluorescence decrease, while in aprotic mixed solvent, there was strong AIE phenomenon. DFT and TD-DFT calculations at the B3LYP/6-31G (d) were performed for a deeper understanding of optical transitions. In addition, in order to investigate the difference of its fluorescence phenomenon, two other barbiturate derivatives were synthesized and their spectra were compared with BNOH. The relationship between hydrogen bond and AIE phenomenon of barbiturates was proved, and the fluorescence mechanism of BNOH in organic solvent was proposed and determined. We believe that this study will not only increase the understanding of barbiturate AIE compounds, but also contribute to the study of the important role of hydrogen bonds in the fluorescence phenomenon of barbiturate AIE compounds. A barbituric acid compound (BNOH) with significant AIE effect, which was resulted from the regular aggregation by the intermolecular hydrogen bonds, has been synthesized in this work. [Display omitted] [ABSTRACT FROM AUTHOR]

• The formation of cocrystal between nitrofurantoin and barbituric acid was investigates, and no related research has been reported. • Dynamic information monitoring of cocrystal synthesis process of barbituric acid and nitrofurantoin. • Research on weak intermolecular interaction in eutectic synthesis of barbituric acid and nitrofurantoin. Cocrystal can effectively improve the physical and chemical properties of active pharmaceutical ingredients, which provides the possibility of changing the key medicinal properties of active pharmaceutical ingredients. This capability has garnered increasing attention in pharmaceutical field. In this study, we synthesized a cocrystal of barbituric acid and nitrofurantoin and characterized it using terahertz and Raman spectroscopy. Density functional theory simulation was used to calculate the terahertz and Raman spectra of the barbituric acid and nitrofurantoin cocrystal. The calculated results indicated that the spectra in the C configuration aligned most closely with the measured vibrational spectra, thus providing confirmation of the synthesis of the cocrystal. The study focused on analyzing intermolecular interactions, vibration modes, and molecular structure in the cocrystal. It is found that intermolecular hydrogen bonds play a crucial role in cocrystal synthesis. These results provide a wealth of information and basic bench marks for investigating the structure and intermolecular interactions of barbituric acid and nitrofurantoin cocrystals. It also provides a reference for the simulation of drug cocrystal formation and the intermolecular hydrogen bond interaction between active pharmaceutical ingredients and various cocrystal based on Raman and terahertz vibrational spectroscopy combined with DFT theory. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract A highly efficient, fast, catalyst‐free, and atom economical method was developed for the synthesis of 5‐benzylidenebarbiturates. Thus, reacting barbituric acid and aldehydes in water as a green solvent under electrochemical conditions afforded the synthesis of the target compounds in six minutes and in highly pure forms. The effects of solvent, reaction time, temperature, electrolyte, and electrode material were studied to optimize the reaction conditions. The scope of the reaction was broadened by the synthesis of 5‐(arylidene)barbiturate derivatives 3 a–3 q using different aldehydes. Calculation of the green chemistry metrics proved the efficiency of the reaction in terms of E‐factor, mass intensity, mass productivity, and reaction mass efficiency. Compound 3 g [5‐(4‐(dimethylamino)benzylidene) barbiturate] was used for the colorimetric detection of cyanide ion over dynamic linear range 1–25 μM with limit of detection (LOD) of 0.86 μM.

Naphthopyranopyrimidine derivatives are an important class of naturally occurring tetraheterocyclic organic compounds that are used as dyes, fluorescent materials for visualization of biomolecules, and in laser technology. Moreover, they are known for biological and pharmaceutical activities. Herein, we briefly reviewed the history of synthesis approaches of naphthopyranopyrimidine and spironaphthopyranopyrimidine derivatives from naphthols, aldehydes/isatins, and barbituric acid/1,3-dimethylbarbituric acid/thiobarbituric acid/1,3-dimethyl-2-thiobarbituric acid/6-amino-1,3-dimethyluracil in the presence of both homogeneous and heterogeneous catalysts reported by research groups. [ABSTRACT FROM AUTHOR]

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The visible light responsive graphitic nitride (g-C3N4) mediated photocatalysis has drawn extensive attention in water treatment field. Carbon doping could improve the photocatalytic activity of g-C3N4 in promoting charge separation efficiency, visible-light utilization, etc. In this paper, the g-C3N4 (as MC) was modified by barbituric acid (as MCB0.07) and further treated by reduced graphene oxide (rGO) (as n%GCN) and then applied to inactivate ofloxacin-resistant bacteria (OFLA) under light irradiation at UVA-visible wavelength. The results showed that the n%GCN presented strong photocatalytic activity when the GO mass ratio was 7.5% (as 7.5%GCN). The inactivation efficiencies of OFLA by MC, MCB0.07, and 7.5%GCN were 5.77 log, 8.48 log, and 8.25 log, respectively, under UVA-visible wavelength (λ > 305 nm), compared to 4.83 log, 5.56 log, and 6.08 log, respectively, within 16 h under visible wavelength (λ > 400 nm). The rGO-doping obviously improved the inactivation efficiency of MCB0.07 on OFLA under visible wavelength. Furthermore, the photoreactivation and dark repair phenomena of OFLA were examined after MC, MCB0.07, and 7.5%GCN treatment, respectively, and it was found that all approaches led to permanent damage to OFLA of which the regrowth was not observed after 24–48 h. Based on the quenching test, reactive oxygen species of O2−• and hole (h+) exhibited dominant roles in the photocatalytic inactivation of OFLA, which may result in oxidative stress and damage to the cell membrane. This study could shed light on the inactivation of OFLA under visible light radiation by rGO modified g-C3N4. [ABSTRACT FROM AUTHOR]

A simple, practical, and efficient one-pot three-component protocol was employed for the synthesis of functionalized 5-aryl-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-diones by reacting barbituric acid, aromatic aldehydes, and substituted anilines using p-toluenesulfonic acid as a readily available and very inexpensive catalyst. The synthesized compounds were characterized by 1H and 13C NMR, FT-IR, and mass spectra and elemental analyses and screened for their in vitro antimicrobial potential against bacterial strains Dickeya sp. and fungal strain Fusarium oxysporum. 7-Nitro-5-(4-nitrophenyl)-5,10-dihydropyrimido[4,5-b]-quinoline-2,4(1H,3H)-dione showed better antimicrobial potential (MIC 3000 µg/mL and MFC 5000 µg/mL) as compared to the other screened compounds. [ABSTRACT FROM AUTHOR]

A concept of piezo-responsive hydrogen-bonded π-π-stacked organic frameworks made from Knoevenagel-condensed vanillin–barbiturate conjugates was proposed. Replacement of the substituent at the ether oxygen atom of the vanillin moiety from methyl (compound 3a) to ethyl (compound 3b) changed the appearance of the products from rigid rods to porous structures according to optical microscopy and scanning electron microscopy (SEM), and led to a decrease in the degree of crystallinity of corresponding powders according to X-ray diffractometry (XRD). Quantum chemical calculations of possible dimer models of vanillin–barbiturate conjugates using density functional theory (DFT) revealed that π-π stacking between aryl rings of the vanillin moiety stabilized the dimer to a greater extent than hydrogen bonding between carbonyl oxygen atoms and amide hydrogen atoms. According to piezoresponse force microscopy (PFM), there was a notable decrease in the vertical piezo-coefficient upon transition from rigid rods of compound 3a to irregular-shaped aggregates of compound 3b (average values of d33 coefficient corresponded to 2.74 ± 0.54 pm/V and 0.57 ± 0.11 pm/V), which is comparable to that of lithium niobate (d33 coefficient was 7 pm/V). [ABSTRACT FROM AUTHOR]

A new synthetic procedure for obtaining two previously reported donor-acceptor butadiene dyes, namely 5-(3,3-bis(4-methoxyphenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione and 5-(3,3-bis(4-(dimethylamino)phenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, based on the InCl3-catalyzed coupling 1,3-diethyl-2-thiobarbituric acid with 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol and 1,1-bis(4-(dimethylamino)phenyl)prop-2-yn-1-ol, respectively, is presented. The reactions, which cleanly proceed in water under MW irradiation, involve the initial generation of the corresponding enals by Meyer-Schuster rearrangement of the alkynols and their subsequent Knoevenagel condensation with the 2-thiobarbituric acid derivative. By following the same approach, the novel butadiene 5-(3,3-bi([1,1′-biphenyl]-4-yl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, which was characterized by 1H and 13C{1H} NMR, IR, UV-Vis, elemental analysis and HRMS, was synthesized in 79% yield. [ABSTRACT FROM AUTHOR]

The bimetallic organic framework nanoenzyme Cu 2 O/Cu-MOF/Fe-MIL-88B is synthesized by the solvothermal method. The characterizations of transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and cyclic voltammetry prove that the amounts of oxygen vacancies are existed on the surface of Cu 2 O/Cu-MOF/Fe-MIL-88B and stronger electron transfer is the key factor for free radical •OH and O 2 ·- production, thus exhibiting excellent peroxidase activity of Cu 2 O/Cu-MOF/Fe-MIL-88B. On the basis of the excellent peroxidase activity, versatile colourimetric and intelligent detection platforms for p-aminophenol and barbituric acid are successfully constructed on site and timely. The linear ranges of p-aminophenol and barbituric acid are 25–75 μM and 5–45 μM, and the lowest limits of detection (LOD) are 0.51 μM and 0.46 μM, severally. Moreover, the mechanisms for detecting p-aminophenol and barbituric acid were displayed by virtual reality technology. Therefore, the colourimetric and intelligent sensor of p-aminophenol and barbituric acid based on the peroxidase of Cu 2 O/Cu-MOF/Fe-MIL-88B have a hopeful prospect in the field of biomedicine. [Display omitted] • Cu2O/Cu-MOF/Fe-MIL-88B presents the peroxidase-like activity. • The peroxidase like mechanism of Cu2O/Cu-MOF/Fe-MIL-88B is studied. • Cu2O/Cu-MOF/Fe-MIL-88B can detect p-aminophenol and barbituric acid. • On-site visual detection platform is established for p-aminophenol and barbituric acid. [ABSTRACT FROM AUTHOR]

The primary aim of this research is to comprehensively assess the applicability of chitosan biopolymer towards water treatment application and to enhance its adsorption capacity towards Remazol brilliant blue R-19 dye. This has been achieved through physical modification to obtain the material in hydrogel form and chemical modification by crosslinking it with barbituric acid. The characterization of the resulting Chitosan-barbituric acid hydrogel (CBH) was carried out using various analytical techniques such as SEM-EDX, FT-IR, TGA-DTA, XRD, and BET. CBH was employed as the adsorbent to eliminate R-19 dye from aqueous media. Utilizing response surface methodology (RSM), the parameters were fine-tuned, leading to the achievement of more than a 95% removal for R-19 dye. The adsorption behavior closely adhered to the Langmuir isotherm and pseudo-second-order kinetics. An interesting observation indicated that the rise in temperature leads to rise in adsorption capacity of CBH. The maximum adsorption capacities evaluated at 301.15 K, 313.15 K, 318.15 K, and 323.15 K were 566.6 mg g−1, 624.7 mg g−1, 671.3 mg g−1, and 713.5 mg g−1 respectively, in accordance with the Langmuir isotherm model. Examining the thermodynamics of the adsorption process revealed its spontaneous nature (ΔG = −21.14 to −27.09 kJ mol−1) across the entire temperature range. Furthermore, the assessment of the isosteric heat of adsorption (ΔH ads) was conducted using the Clausius–Clapeyron equation, with results indicating an increase in ΔH ads from 1.85 to 2.16 kJ mol−1 with temperature rise from 301.15 K to 323.15 K due to augmented surface loading. This suggested the existence of lateral interactions between the adsorbed dye molecules. The potential of adsorbent for regeneration was investigated, demonstrating the ability to reuse the material. Sustainability parameter calculated for synthesis process reflected a notably low E-factor value of 0.32 demonstrated the synthesis is environment friendly. [Display omitted] • Chitosan was crosslinked using barbituric acid to get hydrogel. • It was characterized and subjected to R-19 dye amputation. • The q m value was increased to 713.5 mg g−1at 323.15 K under optimum conditions. • RSM was used to optimize the pH, dose, time and concentration against temperature. • Studies of regeneration demonstrated that the adsorbent CBH is economically viable. [ABSTRACT FROM AUTHOR]

Magnetic nanofiber cellulose (NFC) was selected as a biopolymer surface for the reaction with ferric metformin and a novel nanocatalyst was prepared. This green heterogeneous organometallic catalyst was analyzed by physiochemical techniques. The new metformin drug complex supported on magnetic NFC was used as a powerful and efficient catalyst for the synthesis of functionalized 4H-pyrans derivatives. The antimicrobial activity of the products showed excellent activity against all the bacterial and fungal strains (especially compounds 7q and 6r). [ABSTRACT FROM AUTHOR]

A detailed kinetic study on the tautomerization reactions of barbituric acid (BA) at elevated temperatures from 270 K up to 1000 K was performed in this work. The B3LYP/6-311 + G(3df,2p) density functional theory (DFT) calculations were performed to evaluate the rate constants of transition states (TS) conversions of the tautomerization reactions. The connections from a given TS to the corresponding local minima of the reactant and product sides were confirmed by means of employing the intrinsic reaction coordinate (IRC) method. Moreover, the quantum theory of atoms in molecules (QTAIM) approach was employed to analyze the molecular mechanisms of reactions. The effects of vibrational normal mode frequencies of the reactant and TS were investigated on the curvature of the corresponding Arrhenius plot in the presence and absence of the tunneling effect. For each tautomerization reaction, the investigated reaction was partitioned into three different stages and four zones. The obtained results were plotted along with the corresponding reaction coordinates for each reaction considering and comparing different factors in agreement with already affirmed concepts. As a consequence, details of performed kinetic study on the tautomerization reactions of BA were successfully provided in this work. [ABSTRACT FROM AUTHOR]

A clean and efficient, multi-component strategy for the synthesis of biologically important trisubstituted thiazole via the reaction of readily available barbituric acid, acetophenone, and aryl thioamides is reported in the presence of FeCl3.6H2O / O2(Air) in DMF solvent. The advantages of the present methodology include a one-pot reaction, environment-friendly approach, cost-effectiveness, broad substrate scope, operational simplicity, short reaction time, easy workup procedure, and high yields. [ABSTRACT FROM AUTHOR]

Formations of bimolecular barbituric acid (BA) complexes through hydrogen-bonding (HB) interactions were investigated in this work. BA has been known as a starting compound of pharmaceutical compounds developments, in which the molecular and atomic features of parent BA in homo-paring with another BA molecule were investigated here. The models were optimized to reach the stabilized structures and their properties were evaluated at the molecular and atomic scales. Density functional theory (DFT) calculations were performed to provide required information for achieving the goal of this work. Six dimer models were obtained finally according to examining all possible starting dimers configurations for involving in optimization calculations. N-H... O and C-H... O interactions were also involved in dimers formations besides participation of the X-center of parent BA in interaction. Molecular and atomic scales features were evaluated for characterizing the dimers formations. As a consequence, several configurations of BA dimers were obtained showing the importance of performing such structural analyses for developing further compounds from BA. [ABSTRACT FROM AUTHOR]

Silica- supported boron trifluoride nanoparticles (BF3. SiO2 NPs) was prepared and used as a mild green solid acid catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives from the reaction of aromatic aldehydes with ethylcyanoacetate and barbituric acid in ethanol. The reaction was efficiently promoted by BF3. SiO2 NPs and the heterogeneous catalyst was recycled for three runs in this reaction without losing its catalytic activity. Reusable and eco-friendly catalyst, simple work up procedure, easy separation of product from reaction mixture, safe and clean reaction giving high yield of the corresponding pyrano[2,3-d] pyrimidine in a short time, are some advantages of this protocol.

Synthesis of one‐dimensional nanofibers with distinct topological (higher‐order structural) domains in the same main chain is one of the challenging topics in modern supramolecular polymer chemistry. Non‐uniform structural transformation of supramolecular polymer chains by external stimuli may enable preparation of such nanofibers. To demonstrate feasibility of this post‐polymerization strategy, we prepared a photoresponsive helically folded supramolecular polymers from a barbiturate monomer containing an azobenzene‐embedded rigid π‐conjugated scaffold. In contrast to previous helically folded supramolecular polymers composed of a more flexible azobenzene monomer, UV‐light induced unfolding of the newly prepared helically folded supramolecular polymers occurred nonuniformly, affording topological block copolymers consisting of folded and unfolded domains. The formation of such blocky copolymers indicates that the photoinduced unfolding of the helically folded structures initiates from relatively flexible parts such as termini or defects. Spontaneous refolding of the unfolded domains was observed after visible‐light irradiation followed by aging to restore fully folded structures. [ABSTRACT FROM AUTHOR]

Background: Cancer is one of the most important reasons for mortality worldwide. Several synthetic products have shown valuable efficiency as an anticancer medicines. Chromene derivatives have long been used as the promising compounds which are potent in inhibition of the growth of tumors. Methods and results: In this study, we investigate an anticancer activity of barbituric/thiobarbituric acid-based chromene derivates. For this purpose, viability, antioxidant and apoptotic assays were conducted using three different cancer cell lines (A2780, MCF7, and A549). In most cases, the antiproliferative activity of barbituric acid-based derivatives was higher than that of thiobarbituric acid-based compounds. Among 14 compounds, compound 4g was the most potent one, which showed the highest effect on cells by increasing the accumulation of ROS (up to 540% increase), increasing the level of caspase-3 and caspase-9 (~ 35% increase), and decreasing the mitochondrial membrane potential (2.5 folds reduction). To characterize the type of cell death involved into our experiment Annexin V/PI double staining of compound 4g was performed. The results showed that the number of late apoptotic and/or necrotic cells (Ann V + /PI +) increased fourfold upon treatment with IC50 concentration of 4g. Conclusions: Overall, the anti-proliferative activity of barbituric acid-based derivatives was higher than that of thiobarbituric acid compounds, and compound 4g can be introduced as a potential candidate to prevent various cancers. [ABSTRACT FROM AUTHOR]