Imine Compounds Research Articles

Engineering electron cloud density of phenazine for high-voltage and long-life alkaline batteries

Alkaline aqueous batteries, with intrinsic high safety and potential for high voltage, have always been a hot research topic. Despite several generations of development of anode materials, they still face the challenge of poor cycling stability. Imines have a significant advantage in stability compared to other n-type materials, but their potential is not low enough compared to metal anodes. Herein, a symmetrically structured, extended π-conjugated imine compound, namely cyano-substituted dotriaconta tetrazaoctacyclo (4CNDTZ), was synthesized for the first time and evaluated as the anode materials for alkaline aqueous batteries. 4CNDTZ exhibits a remarkable capacity of 250 mAh g-1 at 0.2 A g-1, coupled with a remarkably low plateau potential of -0.81 V (vs. SHE), significantly below that of conventional alkaline battery anodes. Advanced characterization techniques alongside theoretical calculations confirm that the active sites crucial for its performance are the CN and CN groups, driving an oxidation–reduction process involving the transfer of 4 K⁺ and 4 electrons. When coupled with Ni(OH)2 cathode, the full cells exhibit a discharge voltage plateau of 1.17 V, allowing the full cells to achieve an energy density of up to 170 Wh kg-1 and sustain stable operation through 10,000 cycles.

D-π-A based Diaminomalenonitrile Imine Compounds as Sensors: From Ion Recognition to Logic Arithmetic Applications

D-π-A based Diaminomalenonitrile Imine Compounds as Sensors: From Ion Recognition to Logic Arithmetic Applications

Waste Polyethylene-Derived Carbon Dots: Administration of Metal-Free Oxidizing Agents for Tunable Properties and Photocatalytic Hyperactivity.

The possibility of converting waste plastics into carbon dots (CDs) with 100% efficiencies using KMnO4 has emerged as a significant discovery in mitigating plastic pollution and upcycling. However, the lack of tunability of their properties, viz. aerial O2 harvesting, light-induced autophagy, and photoactivity using air as a free oxidant, has remained a bottleneck. Besides, the toxicity of KMnO4 makes the process less sustainable. Attempting to bridge these gaps, herein, we demonstrate the preparation of CDs using polyethylene with enormous controllability of their properties by utilizing less-toxic and metal-residue-free oxidizers, e.g., H2O2, HNO3, HClO4, and NaClO. We obtain structurally diverse CDs with controllable luminescent quantum yields (∼0.5-8%), excitonic lifetimes (1.3-2.3 ns), and binding energies (147-290 meV). These CDs exhibit a hugely extended range of molecular O2 harvesting (∼405-650 μM) with different amounts of strongly and weakly surface-bound O2 molecules within an estimated ratio of ∼0.77-2.51. Autophagy varied from 14 days to a nearly "no-autophagy" show. We efficiently utilized their oxygen harvesting and photocatalytic abilities to synthesize imine compounds from the corresponding amines in the open air (rate constant of ∼0.055 min-1), surpassing the literature efficiencies achieved using an O2 flow and noble metals. Notably, due to oxygen harvesting by CDs, no additional rate enhancement was observed after O2 purging, establishing the role of CDs in making free air an excellent oxidizing agent.

Theoretical and experimental investigations on structural, electronic and biological properties of novel carbazate containing furaldehyde based imines

A convenient and facile synthesis of tert‑butyl (E)-2-(furan-2-ylmethylene) hydrazine-1-carboxylate (a) and ethyl (E)-2-(furan-2-ylmethylene) hydrazine-1-carboxylate (b) were accomplished by refluxing t‑butyl/ethyl carbazate with a furaldehyde in solvent ethanol. The interactions between and within two synthesised imine compounds were characterised and identified by the utilisation of spectroscopic techniques in conjunction with X-ray crystallography and theoretical computations. Compound a crystallises in orthorhombic crystal system with Pbca space group, while as compound b crystalizes in monoclinic crystal systems with space groups Cc. The presence of CH…π stacking and π…π stacking interactions are distinguishing characteristic of crystal packing in both target compounds. Their solid-state behaviour was also studied using Hirshfeld surfaces. Crystal packing motifs were investigated with the aid of Hirshfeld surface fingerprint plots. Furthermore, investigations related to calculations of the molecular electrostatic potential and frontier molecular orbital (highest occupied-lowest unoccupied) were carried out for the optimised structure. Finally, Hormone-sensitive lipase (HSL) (PDB-ID 6KEU) protein was used to conduct molecular docking investigations of compound a and b.

Fused double oxazolidine vs Imine ligands and Zn-complexes formation: Experimental and theoretical calculations

The condensation reaction between minodiols and carboxaldehydes offers the possibility to obtain either 1-aza-3,7-dioxabicycle[3.3.0]octane (namely here as fused double oxazolidine) or imine compounds. Till now, only limited information is available regarding the factors influencing this behavior. Thus, the present work explored the substituent effect on the reactivity of aminodiols with pyridine carboxaldehydes both in the presence and absence of Zn (II). Without the presence of the metal, the condensation reactions favor the production of fused double oxazolidine derivatives, with identification of both cis and trans isomers in relation to the pyridyl moieties. Notably, the presence of a methyl substituent favors the trans isomers owing to the steric hindrance effect, while a hydrogen substituent favors the cis isomers. Conversely, in the presence of ZnCl2, the main product is the imine-metal complex when the substituent is a methyl group. However, in the presence of a hydrogen substituent, both the imine-metal and the fused double oxazolidine-metal complexes were produced as a mixture in similar proportions. These experimental results are supported by theoretical calculations.

In silico approach through molecular docking and study ADME on imine derivative compounds as a potential antibacterial agent against Staphylococcus aureus

Background: Antibiotics are drugs or compounds that inhibit or kill bacteria. Most natural and synthetic pharmacophores have been reported to be antimicrobial agents. One of these is an imine compound. Compounds containing imine groups exhibit various pharmacological activities, including antibacterial, antifungal, anti-HIV, anti-cancer, anti-inflammatory, antimalarial, and antituberculosis activities. Objective: This study aimed to determine the potential of four imine-derived compounds as antibacterial agents using molecular docking. Method: The molecular docking environment (MOE) 2022.0901 software package was used to perform molecular docking. Determination of the physicochemical and pharmacokinetic properties of the four imine-derivative compounds was performed online via the website www.swissadme. Results: Based on the docking results, compound 1 has great potential as an antibacterial agent because its binding orientation was similar to that of the positive control. In addition, based on the Absorption, Distribution, Metabolism, and excretion (ADME) study, compound 1 was shown to be suitable for Lipinski's rule of five (RO5). Conclusion: It can be concluded that compound 1 is easily absorbed, has good permeability, and can be used as a promising agent against Staphylococcus aureus.

Indolyl imine compounds as multi-target agents; synthesis, antidiabetic, anticholinesterase, antioxidant activities and molecular modeling

A new range of indolyl imine system 3d-l has been successfully prepared from 4,6-dimethoxy-2,3-diphenyl-indole-7-carbaldehyde 2a and 4,6-dimethoxy-3-aryl-indole-7-carbaldehyde 2b-cvia Schiff base reaction. The structure of targeted compounds was confirmed by 1H and 13C NMR, FT-IR, mass spectrometry and single crystal X-ray diffraction techniques. The indolyl imine derivatives were also subjected to in vitro antidiabetic activities employing α-glucosidase and α-amylase enzymes. In terms of antidiabetic investigation, the α-glucosidase enzyme was found to be potential target due to the comparable inhibition concentrations with the standard acarbose and the compound 3e exhibited better potency than the standard. The anticholinesterase potency of the compounds was investigated towards the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. The compounds displayed moderate efficiency against the BChE enzyme with the best inhibition concentration of 30.48 μM by the compound 3h. The antioxidant properties of final compounds were determined by DPPH radical scavenging, ABTS Cation Radical Decolarization and CUPRAC Cupric Reducing Antioxidant Capacity assay methods. The ABTS cation scavenging assay provided the best responses for the compounds and the candidates 3k and 3l were determined as promising targets for the antioxidant activity. Plausible binding mode and interaction of ligands with the selected enzyme have been studied by molecular docking, supporting the experimental results. In silico ADME showed high drug likeness of the synthesized compounds.

Synthesis of reduced graphene oxide-based hybrid materials containing imine bonds: Color properties and chemosensory properties against some anions

In this research, hybrids (HBa and HBb) were synthesized by covalent bonding of Schiff bases with reduced graphene oxide (RGO) synthesized by the modified hummer method and hydrothermally reduced. To facilitate the covalent bonding, the (–COOH) group of RGO was converted to (-COCl) with SOCl2 and Schiff bases (5) and (6) containing 1,2,3-triazole were attached to RGO. All materials were characterized using spectroscopic and analytical methods. Color changes of hybrid materials were investigated in the availability of some anions under three different light sources: daylight, long wavelength, and short wavelength light. It was observed that the end groups (Cl and Br) of the imine compounds were effective on the chemosensory property. Unlike HBa (Br), the HBb (Cl) hybrid exhibited selective sensory properties towards CO32–, CH3COO– ions. In addition, it was concluded that the materials showed blue emission according to the calculated CIE (1931) chromaticity diagram.

BODIPY- imine based fluorescence “turn on” chemosensor for selective sensing of Hg2+

The detection of mercury has gained considerable attention due to its both environmental and biological impacts. In this study, a BODIPY- imine chemosensor (3) having an imine molecule at the meso position of the BODIPY core was synthesized, and its structure was characterized by spectroscopic and analytical methods as well as single crystal XRD. Chemosensor 3 showed a poor emission band in the DMSO/H2O (9:1 v/v) solvent system (ΦFl < 0.01). Upon the addition of Hg2+, the fluorescence intensity of 3 increased notably with a 0.031 ΦFl value, and the limit of detection for Hg2+ was calculated as 0.90 μM. The sensing mechanism of 3 was investigated 1H NMR titration studies and Hg2+ ion induced hydrolysis of the imine double bond and thus activating the PET OFF proccess. The BODIPY- imine compound (3) can be used as reaction-based fluorescence probe for the sensing of Hg2+ ion.

Determination of mutagenic potentials of diarylmethylamine based imine compounds by ames test and computational molecular docking

In recent years, studies that investigate the effects of chemical compounds on organisms have increased in direct proportion to their widespread use. In this study, four different bidentate imine ligands and bidentate imine ligands+Cu(II) complexes were synthesized from the bioactive synthetic diarylmethylamine compound. After the ligands and metal complexes obtained were purified using chromatographic and analytical methods, their mutagenic effects were investigated with the Ames/Salmonella test system. In addition, interactions of four different Cu(II) complexes with B-DNA were evaluated with molecular docking analysis. Accordingly, the results indicated a significant increase in the colonies formed in the presence (+S9) and absence (-S9) of the metabolic activation system, meaning a mutagenic effect against strain TA98 and TA100 strains in general.

Tetradentate azo Schiff base Ni(II), Pd(II) and Pt(II) complexes: Synthesis, spectral properties, antibacterial activity, cytotoxicity and docking studies

A new complexes of Ni(II), Pd(II), and Pt(II) have been synthesized from the reaction of Azo-Schiff base ligand (L1) that was prepared by the condensation firstly of salicylaldehyde with ethylene diamine in a 1:2 molar ratio and the prepared imine compound (S1) reacted with 2,5-dichloro aniline, and were employed in the preparation of complexes containing the metal ions Ni(II), Pd(II), and Pt(II). The structural characteristics of the synthesized compounds were investigated using UV-Vis, IR and NMR, molar conductance, elemental analysis, and mass spectroscopy. The results of the elemental analysis point to a 1:1 [M:L] stoichiometry. According to molar conductance studies, none of the prepared end products are electrolytic in nature. The complexes of Ni(II), Pd(II), and Pt(II) may have square planer geometry, according to spectral investigations. Then Pd(II), Ni(II), and Pt(II) complexes were evaluated for antimicrobial activity against different types strains of Gram-negative [Escherichia coli (ATCC 25922)] and positive bacteria [Staphylococcus aureus (ATCC 25923)] and showed good significant against these bacteria. The cytotoxic effect of the palladium complex on the prostatic malignant cell was examined via the PC3 cell line studied against normal cell WRL-68. The molecular docking of target microorganisms of these complexes will be studied by using MOE software.&#x0D; KEY WORDS: Salen ligand, Nickel(II), Palladium(II), Platinum(II), Complexes, bis azo-Schiff base&#x0D; Bull. Chem. Soc. Ethiop. 2024, 38(1), 99-111. DOI: https://dx.doi.org/10.4314/bcse.v38i1.8

Synthesis, Characterization, ADME Study and Anti-proliferative evaluation against MCF-7 breast cancer cell line of new analog of a 4-aminophenyl quinazolinone derivative

New series of 4-aminophenyl quinazolinone attached to an aromatic aldehyde moiety has been designed. Compound (ZA) was synthesized by a reaction of benzene-1,4-diamine with 2-aminobenzoic acid.&#x0D; The reaction between (ZA) intermediate and different substituted aromatic aldehydes (R1- R6) is considered one of the most common chemical reactions for the synthesis of imine compounds (Schiff bases) to produce compound (ZA1-ZA6). FTIR, 1H-NMR, and 13C-NMR have been used to confirm the chemical structures of various substances. MTT assay was used to assess in vitro anti-proliferative action for estrogen receptor alpha. The anti-proliferative study discovered a dose-dependent effect on cell proliferation in breast cancer (MCF-7) with inhibitory concentration In comparison to the reference medication tamoxifen (IC50 of 133.4µg\mL), IC50 of the compounds (ZA1, ZA2, ZA3) was 0.07964, 57.43 &amp; 0.002717 µg\mL, respectively at 72 hours on same cell line mentioned above, that also signifies that compound ZA1 has a significantly greater effect on this cell line type

Antioxidative capacity evaluation of imine compounds as metal ions chelators and free radical scavengers in biodiesel

Factors affecting the oxidation stability of commercially available biodiesel were primarily investigated using the acid value (AV), peroxide value (PV), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, and thermogravimetric (TG) analysis in the presence of imine antioxidants. In this study, the imine compounds N,N′-bis-(4-octadecanate)-salicyl ethylenediamine (stearic dhben) and N,N′-bis-(4-hexadecanate)-salicyl ethylenediamine (palmitic dhben) were synthesized to evaluate their abilities as metal chelators and oxygen scavengers. The AV analysis showed a slight difference between the samples with and without copper. The PV tests demonstrated that both imines were efficient free radical scavengers and copper ion chelators at both room temperature and 50 °C, outperforming the commercial antioxidants butylhydroxytoluene (BHT) and tert-butylhydroquinone (TBHQ). The Derivative Thermogravimetry (DTG) curves indicated that both imines were more effective compared to commercial antioxidants. In the DPPH assay, it was observed that the palmitic dhben imine exhibited the best performance, with an half maximal inhibitory concentration (IC50) of 12.4·10−5 mol L−1. Therefore, both stearic and palmitic dhben imines act as efficient biodiesel antioxidants at room temperature and 50 °C, functioning as excellent metal chelators and free radical scavengers. However, stearic dhben demonstrated better performance as a metal chelator, whereas palmitic dhben was more effective as a free radical scavenger.

UV-Vis spectroscopic and colorimetric anion detection and fluorescence properties of new 3-amino-4-hydroxybenzenesulfonic acid-based Schiff bases depending on the strength and position of the electron donor substitution

In this study, 3-amino-4-hydroxybenzenesulfonic acid-based imine compounds; 3-(2,5-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (1), 3-(2,4-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (2) and 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3) was synthesized. The compounds were analyzed using various spectroscopy methods, and the experimental UV–vis data matched the theoretical predictions. The compound 1 displayed lower stability, higher reactivity, and easier photoexcitation due to a smaller HOMO-LUMO energy gap. The investigated compounds 1-3 showed promise as chemosensors for anions, providing visible detection in daylight conditions. The compound 3 exhibited selective fluorescence at specific wavelengths. The compounds 1-3 interacted with DNA through electrostatic interactions. Also, compounds 1-3 showed higher antioxidant activity than BHT. However, fluorescence measurements indicated that the emission signals were strongly influenced by the position and strength of the electron-donating group. Adding a hydroxy or methoxy moiety near the -OH group on the phenyl ring decreased the fluorescence signal due to intersystem crossing and intramolecular charge transfer mechanisms, respectively. These findings were supported by femtosecond transient absorption spectroscopy measurements. The results emphasize the significance of substituents in imines derived from 3-amino-4-hydroxybenzenesulfonic acid in determining their biological activities, as well as their optical and sensor properties.

Polycyclic aromatic‐based fluorescent probes: Color properties and fluorimetric detection of nitroaromatic explosives

AbstractDetection of nitroaromatic explosives (NAEs) is very important in terms of national security as well as the damage they cause to living things and the environment. The precision detection of these is a very important issue to reduce their harmful effects and take the necessary precautions. Electron‐rich polyaromatic fluorescent materials are highly sensitive and selective in the detection of NAEs in terms of their fluorometric quenching abilities. Three imine compounds (A‐C) containing pyrene, anthracene or naphthalene moieties were prepared and used as fluorescent probes for fluorescence detection of NAEs. The sensing abilities of materials characterized by traditional methods were investigated. The quenching‐increasing constant Ksv was calculated by using the Stern‐Volmer plot obtained from the interaction of materials with nitroaromatic. Limits of detection (LOD) values were calculated for the compounds using these data. While the quenching effect of nitro aromatic compounds was expected on fluorescent materials, increased emission was observed due to aggregation. Compound A was sensitive to Picric acid thanks to lowest LOD (38.59 μM), while compounds B and C nitrobenzene thanks to lowest LOD value (22.32 and 36.93 μM, respectively). In addition, color measurements (CIE standards) and color temperature (CCT) of the compounds were calculated.

Synthesis of Pyridine-Based Imine Compounds and Molecular Docking Studies Against Dopamine D2 Receptors

In this study, new pyridine-based imine compounds (8-10) were synthesized and docking studies of these compounds against D2 Dopamine receptor (6CM4) were performed. The structures of these compounds, which were synthesized using the microwave method, were determined by 1H-NMR, 13C-NMR and elemental analysis techniques. The binding energy values vary range from -6.79 to -7.07 kcal/mol with D2 Dopamine Receptor/PDB: 6MC4. Compound 10 (-7.07 kcal mol-1) showed better binding energy than 9 (-6.95 kcal mol-1) and 8 (-6.79 kcal/mol).

Synthesis, spectral characterization, SC-XRD, Hirshfeld, DFT and in silico antidiabetic activity of novel imine (E)-N-(2-nitro benzylidene) naphthalene-1-amine, a newly synthesized imine: A theoretical and experimental evaluation

A novel imine compound, (E)-N-(2-nitrobenzylidene) naphthalene-1-amine (NBNA), has been successfully synthesized through the reaction of o-nitrobenzaldehyde and 1-naphthylamine. The structural characterization of NBNA has been carried out using single-crystal X-ray diffraction (SC-XRD) analysis. The XRD analysis reveals that NBNA crystallizes in a monoclinic crystal system with the space group P21/c. The unit cell parameters of NBNA are determined as follows: a = 7.549 (4) Å, b = 19.680 (11) Å, c = 9.598 (6) Å, β = 107.96(3)°, and Z = 4. Notably, the crystal structure of NBNA is stabilized by π-π stacking interactions between the naphthyl moiety and the nitrophenyl moiety, occurring at a perpendicular distance of 3.542 Å. Quantum mechanical calculations employing the B3LYP/6–311G(d,p) method in GAUSSIAN 09 software have been employed to determine the optimized geometry, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO), Time-dependent Density Functional Theory (TD-DFT), and chemical reactivity descriptors of NBNA. The vibrational spectroscopic data has been compared with the DFT/B3LYP/6–311G(d,p) method and scaled using MOLVIB for analysis. By examining the NBOs, the distribution of electron density and the interaction between orbitals can be analysed, shedding light on the stability and reactivity of the compound. Additionally, frontier molecular orbital analysis and molecular electrostatic potential mapping are discussed to gain further insights. First-order hyperpolarizability studies have been conducted to explore the nonlinear optical behaviour of the molecule. By calculating and comparing the first-order hyperpolarizability of the compound with a reference molecule (in this case, urea), the obtained results indicate that the crystal of the molecule possesses a significantly higher first-order hyperpolarizability value (19.124 times urea) suggesting its potential as a promising material for nonlinear optical applications. An in-depth examination of the Hirshfeld surface and two-dimensional fingerprint plot has been conducted to gain insights into the intermolecular interactions of the compound. Molecular docking studies are performed on the PPARγ target to assess the molecule's potential antidiabetic activity, revealing a binding energy of -6.71 kJ/mol for NBNA with the target. The comprehensive assessment of the compound's ADMET properties provides valuable insights into its pharmacological potential and aids in the selection of promising drug candidates.

Synthesis, Characterization and Studying of Biological Activity of some new Six–membered Compounds derived from Schiff bases

A series of six - membered rings has been synthesized from Dapsone drug. In the first step examination Dapsone has been taken as initial material and treated with different aromatic aldehydes to prepare new Schiff bases compounds. then imine compounds react with (2-aminobenzoic acid and 2-mercaptobenzoic acid) to prepare Hydroqinazoline and Thiazinone derivatives. In the second step all these derivatives were tested against different bacteria (Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Bacillus anthracis). The high efficacy results of these derivatives proved significantly greater than the efficacy of the same Dapsone drug. These compounds were identified and confirmed by FT- IR, 1HNMR and 13C-NMR.

Design and Synthesis of Imine Derivatives: DFT, Molecular Docking and Antimicrobial Analysis

AbstractFifteen imine compounds were synthesized from the condensation of (Z)‐3‐(4‐bromophenyl)‐3‐(5‐methyl‐2‐thioxo‐1,3,4‐thiadiazol‐3(2H)‐yl) acrylaldehyde and various derivatives of primary amine, and their crystal structure was validated by single‐crystal XRD. Hirshfeld surface studies comprehensively explore intermolecular interactions in crystal packing. A state‐of‐the‐art dual computational strategy using quantum chemistry and molecular docking methodologies illuminates the molecular structure, electronic characteristics, and bioactivity of synthesized imines. Optimized and experimental molecule geometries were compared. By the agar well diffusion method, the synthesized imines were tested for antibacterial and antifungal activity against E. Coli, S. Aureus, A. Niger, and C. Albicans respectively. Based on their biofunctions synthesized imine derivatives were tested for their ability to inhibit E. Coli, C. Albicans, and ACE2. We observed that imine interaction energy values were excellent. We anticipate the current combination study using experiments and computational tools will attract the scientific community and inspire further in vitro and in vivo research.

Synthesis, characterization, antibacterial and anticancer activities of some heterocyclic imine compounds

Schiff Base compounds are among the most important organic compounds that have an important role in the medical field due to their various biological properties. In this work, four new imine compounds (3, 4, 7 and 8) were synthesized in dichloromethane at room temperature from two heterocyclic aromatic aldehydes and three compounds of primary amines. The new compounds were identified by FTIR, 1H and 13C NMR analysis. In 1H-NMR the hydrogen of imine bonds was observed at 8.02-8.3 ppm and the carbon of imine bonds was observed at 153.82-164.89 ppm. Also, C=N double bond was observed around 1650 cm−1 in FTIR spectra. All compounds were tested for their antibacterial as well as anticancer activities.