Imidazole Research Articles

Iridium(III) complexes with cyclometalated imidazolylidene ligands: sp2 phenyl C[sbnd]H activation vs sp2 benzyl C[sbnd]H activation and catalytic transfer hydrogenation reactions

Cyclometalated N-heterocyclic carbene (NHC) complexes possess fascinating electronic and catalytic properties. A series of cyclometalated iridium(III) complexes have been synthesized from the corresponding imidazolium salts via the aryl sp2 CH bond activation at the N1-phenyl/N3-benzyl wingtips of the imidazolylidene moiety. The electronic tuning towards the competitive formation of cyclometalated complexes (sp2 phenyl CH activation vs sp2 benzyl CH activation) has been discussed. These complexes have been utilized for the transfer hydrogenation (TH) reaction of 4-bromobenzaldehyde and 4-bromoacetophenone. These complexes showed excellent yields of the aryl-alcohols from 4-bromobenzaldehyde or 4-bromoacetophenone.

Indazole-5-amine (AIA) as competing corrosion coating to Benzotriazole (BTAH) at the interface of Cu: A DFT and BOMD case study

This study compares three organic compounds—benzotriazole (BTAH), imidazole (IM), and indazole-5-amine (AIA)—as corrosion inhibitors for copper substrates. Using Density Functional Theory (DFT) and Born-Oppenheimer Molecular Dynamics (BOMD) calculations, it identifies AIA as a promising and cost-effective alternative to the toxic BTAH. The adsorption strength on Cu(100) surfaces is ranked AIA>BTAH>IM for both neutral and deprotonated forms. These findings are supported by electronic parameter studies, including Bader charge analysis, density of states (DOS), charge density differences (CDD), and frontier molecular orbital analysis. AIA shows the best adsorption in a parallel orientation at the top site. Packing studies reveal that hydrogen bonding stabilizes the interaction energies within self-assembled AIA aggregates. Organometallic complexation studies reveal that deprotonated BTAH exhibits higher interaction energy with a single Cu atom compared to AIA when bonded through the carbon end, consistent with the findings from BOMD studies. However, on periodic Cu surfaces, AIA outperforms BTAH molecules as seen from adsorption energies. This investigation highlights AIA’s potential as a superior and more economical corrosion inhibitor for copper.

Discovery of Unprecedented Human Stercobilin Conjugates.

Two unique metabolites (M18 and M19) were detected in feces of human volunteers dosed orally with [14C]inavolisib with a molecular ion of parent plus 304 Da. They were generated in vitro by incubation with fecal homogenates and we have evidence that they are formed chemically and possibly enzymatically. Structural elucidation by high resolution mass spectrometry and nuclear magnetic resonance spectroscopy showed that the imidazole ring of inavolisib was covalently bound to partial structures derived from stercobilin, an end-product of heme catabolism produced by the gut microbiome. The structural difference between the two metabolites was the position of methyl and ethyl groups on the pyrrolidin-2-one moieties. We propose a mechanism of M18 and M19 generation from inavolisib and stercobilin whereby nucleophilic attack from the imidazole ring of inavolisib occurs to the bridging carbon of a stercobilin molecule. The proposed mechanism was supported by computational calculations of molecular orbitals and transition geometry. SIGNIFICANCE STATEMENT: We report the characterization of two previously undescribed conjugates of the phosphoinositide 3-kinase inhibitor inavolisib, generated by reaction with stercobilin, an end-product of heme catabolism produced by the gut microbiome. These conjugates were confirmed by generating them using in vitro fecal homogenate incubation via nonenzymatic and possibly enzymatic reactions. Given the unique nature of the conjugate, it is plausible that it may have been overlooked with other small molecule drugs in prior studies.

Sensitive detection of histamine utilizing the SERS platform combined with an azo coupling reaction and a composite hydrophobic layer

Herein, the surface-enhanced Raman scattering (SERS) platform was combined with an azo coupling reaction and an aluminum alloy covered with a hydrophobic layer of praseodymium oxide and stearic acid complexes for the detection of histamine. The praseodymium oxide on aluminum alloy was successfully synthesized by the rare-earth-salt-solution boiling bath method and modified by stearic acid. Its surface exhibits a water contact angle (WCA) of 125.0°. Through the azo derivatization reaction with 3-amino-5-mercapto-1,2,4-triazole (AMTA) diazonium salts, histamine can be converted into the derivatization product with higher Raman activity. The mixture of the derivatization product and β-cyclodextrin-modified Ag nanoparticles (β-CD-AgNPs) were dropped onto the surface of an aluminum alloy covered with a hydrophobic layer of praseodymium oxide and stearic acid complexes, and dried for SERS measurement. The intensity ratio between the SERS peaks at 1246 cm−1 and 1104 cm−1 (I1246/I1104) of the derivatization product was used for the quantification of histamine. Under the selected conditions, the limit of detection (LOD) and the limit of quantification (LOQ) for this method were 7.2 nM (S/N = 3) and 24 nM (S/N = 10), respectively. The relative standard deviation (RSD) of this method for the determination of 1 μM histamine was 6.1 % (n = 20). The method was also successfully used for the determination of histamine in fish samples with recoveries ranging from 92 % to 111 %. The present method is simple, sensitive, reliable, and may provide a new approach for preparing the composite hydrophobic layer that can enhance SERS signals through hydrophobic condensation effect. Meanwhile, it may have a promising future in the determination of small molecular compounds containing an imidazole ring.

Conversion of sugars into methyl lactate over poly (ionic liquid)s functionalized Sn/beta zeolites

Methyl lactate (MLA) is a versatile high value platform chemical prepared from biomass carbohydrates, with widely application in the pharmaceutical, food, pesticide, and cosmetics. The current study presented a one-pot catalytic conversion of sugars to MLA over poly (ionic liquid)s functionalized Sn/Beta zeolites under mild conditions. The Sn/Beta zeolites were prepared by an impregnation method, followed by modification with poly (vinyl imidazole) ([PVIM]) via an in-situ free radical polymerization method. Dosages of polymer and Sn, calcination temperature, reaction temperature, catalyst amount, substrate concentration, and reaction times were optimized. Results showed that an MLA yield of 61.4 % was obtained over 3[PVIM]-Sn/Beta with complete conversion of fructose at 140 °C for 8 h. The physicochemical properties were characterized by XRD, BET, FTIR, CO-DRIFTS, NH3-TPD and pyridine-FTIR analysis, indicating the coexistence of Lewis and Brønsted acid sites. Finally, a possible reaction mechanism was proposed that the weak Lewis acidity of imidazole rings of [PVIM] effectively regulated the local microenvironment of active sites, thus promoting the interaction of the active sites with electronegative oxygens of sugars. This study can provide as a reference for the development of solid acid catalysts for the catalytic conversion of biomass to platform chemicals.

Copper (II) and cobalt (II) bis(hexafluoroacetylacetonate) coordination complexes with N-styrylbenzimidazole

The study considers metal complexes based on N-styrylbenzimidazole as compounds having significant pharmacological properties The work is aimed at examining the crystal structure and electronic structure of transition metal bis(hexafluoroacetylacetonate) complexes (copper (II) (complex A) and cobalt (II) (complex B)) with N-styrylbenzimidazole using X-ray diffraction analysis and ultraviolet spectroscopy. The X-ray diffraction analysis was used to prove bipyramidal coordination in copper (II) and cobalt (II) bis(hexafluoroacetylacetonate) complexes with N-styrylbenzimidazole. The atoms of copper (II) and cobalt (II) in the complexes exhibit an unusual for β-diketonate complexes distorted square-planar coordination, while the chelate cycles in M(hfacac)2L are characterized by anomalously large kink angles. Thus, for the copper (II) bis(hexafluoroacetylacetonate) complex, the kink angle of the O3∙∙∙O4 interaction for the equatorially positioned ligand is 29.47°, while for the axially positioned ligand, the kink angle of the O1∙∙∙O2 interaction is 19.13°. For the cobalt (II) bis(hexafluoroacetylacetonate) complex, these angles are 22.10 and 19.50°, respectively. Electron spectroscopy was used to examine the electronic structure of the specified complexes. The following types of electronic transitions were identified: π→π*-transitions primarily localized on ligands, as well as transitions caused by electron transfer from the p-orbital of the hetero nitrogen atom of the styrylbenzimidazole cycle to the d-orbital of metal ions, and n→π transition localized on the imidazole ring. For each of the complexes, d-d* transitions between the molecular orbitals of the corresponding metal ion were localized in the long wavelength part of the spectrum.

Heterogenization of Ionic Liquid on Multiwalled Carbon Nanotubes for Lead(II) Ion Detection.

The presence of lead(II) ion poses a significant threat to water systems due to their toxicity and potential health hazards. The detection of Pb2+ ions in contaminated water is very crucial. The ionic liquid functionalized multiwalled carbon nanotubes (IL@MWCNT) nanocomposite was fabricated using ionic liquid (IL) 1-methyl-3-(4-sulfobutyl)-imidazolium chloride and multiwalled carbon nanotubes (MWCNTs) for detection of lead(II) ions. It is a novel method to heterogenize the layer of IL on the surface of MWCNTs. The XPS and FTIR analyses confirm that the ionic liquid is not decomposed during annealing process. Moreover, the XRD analysis shows the presence of MWCNTs and carbon quantum dots (CQDs). The HRTEM results exhibit the aggregation of MWCNTs with IL, and formation of small distorted round shaped flakes of CQDs. Further, the successful heterogenization of IL on the surface of MWCNTs is also confirmed by TGA-DSC analysis. The quenching phenomenon of nanocomposite was observed by UV-Visible spectroscopy. The nanocomposite exhibits high performance for the selective detection of lead(II) ions in comparison to other metal ions. The presence of lead(II) ions eventually reduced the intensity of absorption. A limit of detection (LOD) of 9.16 nM was attained for Pb2+ ions in a concentration range of 0-20 nM.

A Review On : To Develop and Validate Analytical Method for Determination of Methimazole in Bulk and Pharmaceutical Dosage Form

Hyperthyroidism is a condition characterized by increased in synthesis and secretion of thyroid hormones from thyroid gland. Methimazole is an anti-hyperthyroidism drug. It is of great importance and significance for life science. Up to now, various different methods have been applied for the determination of methimazole, such as spectrophotometry1-3, LC4, HPLC6, RP-HPLC7, HPLC-UV8, electrochemical analysis9, kinetic method10. In this paper, a new UV-Spectrophotometric method for the determination of methimazole has been established. The chemical name of Methimazole is (1-methylimidazole-2-thiol). The chemical formula of Methimazole is C4H6N2S and the molecular weight is 114.17 g/mol. The structure of Methimazole features a 5 membered imidazole ring with a methyl group at position 1st and thione group at position 2nd. Methimazole is white colour powder and has melting point 1440 C.

Imidazolium salt’s toxic effects in larvae and cells of Aedes aegypti and Aedes albopictus (Diptera: Culicidae)

Aedes aegypti and Aedes albopictus are the main vectors of arboviruses such as Dengue, Chikungunya and Zika, causing a major impact on global economic and public health. The main way to prevent these diseases is vector control, which is carried out through physical and biological methods, in addition to environmental management. Although chemical insecticides are the most effective strategy, they present some problems such as vector resistance and ecotoxicity. Recent research highlights the potential of the imidazolium salt "1-methyl-3-octadecylimidazolium chloride" (C18MImCl) as an innovative and environmentally friendly solution against Ae. aegypti. Despite its promising larvicidal activity, the mode of action of C18MImCl in mosquito cells and tissues remains unknown. This study aimed to investigate its impacts on Ae. aegypti larvae and three cell lines of Ae. aegypti and Ae. albopictus, comparing the cellular effects with those on human cells. Cell viability assays and histopathological analyses of treated larvae were conducted. Results revealed the imidazolium salt’s high selectivity (> 254) for mosquito cells over human cells. After salt ingestion, the mechanism of larval death involves toxic effects on midgut cells. This research marks the first description of an imidazolium salt's action on mosquito cells and midgut tissues, showcasing its potential for the development of a selective and sustainable strategy for vector control.

Revisit coupling of CO2 to ethylene carbonate with an integrated imidazolium and zinc halides catalyst by a study on its decomposition: Active center and mechanism

Coupling of carbon dioxide (CO2) to cyclic carbonates with an epoxide and further into linear carbonates as the indispensable solvents for the lithium-ion batteries has been being one of the hottest topics in transforming CO2 into high value-added chemicals. Nevertheless, the extremely ultrahigh purity requirement for them causes a low efficiency and a modest yield due to the undesired reactions and byproducts occurring in the separation and purification sections. In this work, a novel imidazolium based ionic liquid catalyst system with different anions and cations was studied by a thorough insight into the decomposition reaction of ethylene carbonate (EC), which reveals the synergistic mechanism of the composite catalysts both in section of cyclic carbonate separation from the catalyst for recirculated utilization and purification from the byproducts, and in section of synthesis with high efficiency. Effects of imidazolium cations and halogen anions in the ionic liquid molecule on EC decomposition were investigated by the elaborately designed experiments, thermodynamic estimations, molecular dynamics simulation and DFT assessment. It was found that combining imidazole salts and zinc halides can greatly boost the activity of EC synthesis and decomposition with the effective structure of catalytic center being [EMIm]ZnX4. Furthermore, it was indicated that Br- has a higher activity for EC synthesis and its reversed pyrolysis, while Cl- will promote a side reaction of ring-opening polymerization of EC. Finally, a most favorable catalyst composition with ZnBr2 and [EMIm]Br for EC synthesis was achieved with a high efficiency in synthesis and a low tendency to initiate the side reactions in separation section.

Ureido-Ionic Liquid Mediated Conductive Hydrogel: Superior Integrated Properties for Advanced Biosensing Applications.

Ionic conductive hydrogels (ICHs) have recently gained prominence in biosensing, indicating their potential to redefine future biomedical applications. However, the integration of these hydrogels into sensor technologies and their long-term efficacy in practical applications pose substantial challenges, including a synergy of features, such as mechanical adaptability, conductive sensitivity, self-adhesion, self-regeneration, and microbial resistance. To address these challenges, this study introduces a novel hydrogel system using an imidazolium salt with a ureido backbone (UL) as the primary monomer. Fabricated via a straightforward one-pot copolymerization process that includes betaine sulfonate methacrylate (SBMA) and acrylamide (AM), the hydrogel demonstrates multifunctional properties. The innovation of this hydrogel is attributed to its robust mechanical attributes, outstanding strain responsiveness, effective water retention, and advanced self-regenerative and healing capabilities, which collectively lead to its superior performance in various applications. Moreover, this hydrogel exhibited broad-spectrum antibacterial activity. Its potential for biomechanical monitoring, especially in tandem with contact and noncontact electrocardiogram (ECG) devices, represents a noteworthy advancement in precise real-time cardiac monitoring in clinical environments. In addition, the conductive properties of the hydrogel make it an ideal substrate for electrophoretic patches aimed at treating infected wounds and consequently enhancing the healing process.

Imidazolium-Based Sulfonating Agent to Control the Degree of Sulfonation of Aromatic Polymers and Enable Plastics-to-Electronics Upgrading.

The accumulation of plastic waste in the environment is a growing environmental, economic, and societal challenge. Plastic upgrading, the conversion of low-value polymers to high-value materials, could address this challenge. Among upgrading strategies, the sulfonation of aromatic polymers is a powerful approach to access high-value materials for a range of applications, such as ion-exchange resins and membranes, electronic materials, and pharmaceuticals. While many sulfonation methods have been reported, achieving high degrees of sulfonation while minimizing side reactions that lead to defects in the polymer chains remains challenging. Additionally, sulfonating agents are most often used in large excess, which prevents precise control over the degree of sulfonation of aromatic polymers and their functionality. Herein, we address these challenges using 1,3-disulfonic acid imidazolium chloride ([Dsim]Cl), a sulfonic acid-based ionic liquid, to sulfonate aromatic polymers and upgrade plastic waste to electronic materials. We show that stoichiometric [Dsim]Cl can effectively sulfonate model polystyrene up to 92% in high yields, with minimal defects and high regioselectivity for the para position. Owing to its high reactivity, the use of substoichiometric [Dsim]Cl uniquely allows for precise control over the degree of sulfonation of polystyrene. This approach is also applicable to a wide range of aromatic polymers, including waste plastic. To prove the utility of our approach, samples of poly(styrene sulfonate) (PSS), obtained from either partially sulfonated polystyrene or expanded polystyrene waste, are used as scaffolds for poly(3,4-ethylenedioxythiophene) (PEDOT) to form the ubiquitous conductive material PEDOT:PSS. PEDOT:PSS from plastic waste is subsequently integrated into organic electrochemical transistors (OECTs) or as a hole transport layer (HTL) in a hybrid solar cell and shows the same performance as commercial PEDOT:PSS. This imidazolium-mediated approach to precisely sulfonating aromatic polymers provides a pathway toward upgrading postconsumer plastic waste to high-value electronic materials.

Ionic Liquids Boost Anthraquinone Hydrogenation over Pd‐based Bimetallic Pincer Catalysts

AbstractA series of bimetallic‐ionic liquid (IL) pincer catalysts Pd−M@IL were synthesized using low Pd‐loading amount (0.3 %) and adopting six kinds of ion liquids with the cation containing the imidazole ring, and then evaluated the catalytic activities toward 2‐ethylanthraquinone hydrogenation reaction with the purpose to produce H2O2. Under the reaction conditions of 60 °C, 0.30 MPa and 15 min reaction time, over the catalysts Pd−La@[BMIm]Ac/alu and Pd−La@[VBIM]Br/alu achieved high hydrogenation efficiency(9.4 g/L and 8.5 g/L) but also high selectivity toward the active anthraquinone (98.9 % and 99.6 %). Through characterizations of STEM, TPD, in‐situ XPS, etc., it illustrates that the pincer catalysts Pd−La@[BMIm]Ac/alu and Pd−La@[VBIM]Br/alu have much better dispersity than the bimetallic Pd−La/alu, these two ionic liquids of [BMIm]Ac and [VBIM]Br provide different local environment around Pd−La sites, which in turn modulate the catalytic activity of the pincer‐catalysts toward anthraquinone hydrogenation. DFT calculations disclose the unique electron transfer between ILs ([BMIm]Ac and [VBIM]Br) and Pd−La clusters and subsequent changes of energy barriers for anthraquinone hydrogenation. The work illuminates a facile strategy to design novel hydrogenation catalysts through combining the pincer microenvironment partially encapsulated by the cation and the anion of ionic liquids with the internal bimetallic sites.

Imidazolium Salts with Heterometallic Complex Anions [Co2Li2(Piv)8]2–: Synthesis, Structures, and Magnetic Properties

Imidazolium Salts with Heterometallic Complex Anions [Co2Li2(Piv)8]2–: Synthesis, Structures, and Magnetic Properties

Synthesis of a Metalla[2]catenane, Metallarectangles and Polynuclear Assemblies from Di(N‐Heterocyclic Carbene) Ligands

The 2,7‐fluorenone‐linked bis(6‐imidazo[1,5‐a]pyridinium) salt H2‐1(PF6)2 reacts with Ag2O in CH3CN to yield the [2]catenane [Ag4(1)4](PF6)4. The [2]catenane rearranges in DMF to yield two metallamacrocycles [Ag2(1)2](PF6)2. 2,7‐Fluorenone‐bridged bis‐(imidazolium) salt H2‐L(PF6)2 (L = 2a, 2b) react with Ag2O in CH3CN to yield metallamacrocycles [Ag2(L)2](PF6)2 with interplanar distances between the fluorenone rings too small for [2]catenane formation. Intra‐ and intermolecular p···p interactions between the fluorenone groups were observed by X‐ray crystallography. The strongly kinked 2,7‐fluorenone bridged bis(5‐imidazo[1,5‐a]pyridinium) salt H2‐4(PF6)2 reacts with Ag2O to yield [Ag2(4)(CN)](PF6) while the tetranuclear assembly [Ag4(4)2(CO3)](PF6)2 was obtained in the presence of K2CO3.

Synthesis of a Metalla[2]catenane, Metallarectangles and Polynuclear Assemblies from Di(N-Heterocyclic Carbene) Ligands.

The 2,7-fluorenone-linked bis(6-imidazo[1,5-a]pyridinium) salt H2-1(PF6)2 reacts with Ag2O in CH3CN to yield the [2]catenane [Ag4(1)4](PF6)4. The [2]catenane rearranges in DMF to yield two metallamacrocycles [Ag2(1)2](PF6)2. 2,7-Fluorenone-bridged bis-(imidazolium) salts H2-L(PF6)2 (L=2 a, 2 b) react with Ag2O in CH3CN to yield metallamacrocycles [Ag2(L)2](PF6)2 with interplanar distances between the fluorenone rings too small for [2]catenane formation. Intra- and intermolecular π⋅⋅⋅π interactions between the fluorenone groups were observed by X-ray crystallography. The strongly kinked 2,7-fluorenone bridged bis(5-imidazo[1,5-a]pyridinium) salt H2-4(PF6)2 reacts with Ag2O to yield [Ag2(4)(CN)](PF6), while the tetranuclear assembly [Ag4(4)2(CO3)](PF6)2 was obtained in the presence of K2CO3.

The application of 2-(3-nitrophenyl)imidazo[1,2-α]pyridine as an effective corrosion-defender for steel in acidic environment

Metal corrosion in acidic settings presents serious problems for many industrial areas. The creation of corrosion inhibitors that are efficient, long-lasting, and ecologically benign is essential. This study introduces a novel corrosion inhibitor, 2-(3-nitrophenyl)imidazo[1,2-α]pyridine (NIP), which was synthesized for protecting mild steel in 1 M HCl. The synthesized NIP was evaluated using Electrochemical Impedance Spectroscopy (EIS), Potentio-dynamic Polarization (PDP), Scanning electron microscopy (SEM), Energy X-ray analysis (EDX), and theoretical approache, including Density Functional Theory (DFT) and Monte Carlo simulations (MCs). NIP demonstrated outstanding protection behavior, reaching a peak of 91.47 % at a concentration of 1.00 mM. PDP studies classified NIP as a mixed-type inhibitor that effectively mitigated both anodic and cathodic reactions. SEM and EDX analysis confirmed the formation of a protective layer on the surface of the structural steels, composed mainly of nitrogen and oxides, indicating the presence of the inhibiting agent. DFT calculations identified the imidazole ring and heteroatoms (N and O) as the active sites for corrosion inhibition. The adsorption behavior of NIP on the metal surface has been studied by means of Monte Carlo simulations. The inhibitory efficiency of NIP was evaluated across a temperature range of 298–323 K, and the results showed a decrease in efficacy with increasing temperature, which provides crucial information for practical applications. The Langmuir model fit indicated a mixed mode of physical and chemical adsorption, with a calculated ΔG°ads value of −33.76 kJ/mol. This novel approach pinpointed reactive sites within the NIP, enhancing our understanding of its protective mechanism at the molecular level.

Room‐temperature self‐healing polyurethanes with high mechanical strength and superior toughness for sensor application

AbstractIt remains enormous challenges to balance the conflict between high strength and toughness mechanical properties and excellent room‐temperature self‐healing abilities of polyurethane elastomers. In this work, we report a recyclable room‐temperature self‐healing polyurethane elastomer with excellent mechanical properties. The prepared polyurethane elastomer (PU‐DA‐Zn0.50) exhibits high tensile strength of 15.33 MPa, high toughness of 76.77 MJ m−3, and high elongation at break of 1604.46% by introducing isophorone diamine (IPDA), 1‐(3‐aminopropyl) imidazole (IMZ) and zinc ions into polymer system to form a dynamic double‐cross‐linked structure (hydrogen bonds and Zn2+‐imidazole coordination bonds). In addition, the tensile strength of fractured polyurethane can reach more than 80% of the original sample after 48 h of self‐healing at room temperature without external stimuli, which is attributed to the kinetics of rapid exchange of Zn2+‐imidazole coordination bonds at room temperature. It is worth noting that the balance between excellent mechanical properties and outstanding room‐temperature self‐healing ability can be optimized by adjusting the Zn2+‐imidazole coordination bond density in the system. Moreover, the dynamic nature of the double‐cross‐linking network endows polyurethane with favorable recyclability. The above remarkable comprehensive performances reveal a great potential of PU‐DA‐Znx elastomer in the fields of wearable flexible electronic devices such as bionic skin, human motion monitoring, and soft robots.

Design, Green Synthesis and in silico Studies of New Substituted Naphtho[1,2-e][1,3]Oxazines as Potential Acetylcholinesterase Inhibitors.

Alzheimer's disease (AD) is a prevalent neurodegenerative condition characterized by progressive cognitive decline and memory impairment resulting from the degeneration and death of brain neurons. Acetylcholinesterase (AChE) inhibitors as the primary pharmacotherapy for numerous neurodegenerative conditions, leveraging their capacity to modulate acetylcholine levels crucial for cognitive function. Recently, oxazine and its derivatives have brought worthy synthetic interest due to their extensive biological activities including, anti-acetylcholinesterase, anti-oxidant, anti-pyretic, anti-tubercular, anti-convulsant, anti-microbial, anti-malarial, and anti-cancer activities. In this study, a series of novel naphtho[1,2-e][1,3]oxazine derivatives has been designed and synthesized with potential of acetylcholinesterase (AChE) inhibition. The target products have been prepared by a one-pot and three-component condensation reaction of 2-naphthol, various aromatic aldehydes, and arylmethanimine in the presence of 3-methyl-1-sulfonic acid imidazolium chloride ([Msim]Cl) as an effective and recyclable ionic liquid catalyst under microwave irradiation solvent-free condition. The chemical structures of all resulting products were confirmed by spectroscopic methods (IR, 1H-NMR, 13C NMR) as well as elemental analysis. The molecular docking studies has also been performed to investigate the synthetic compounds in the the AChE active site gorge. The results showed that all these derivatives interact with the enzymes with high affinity in binding pocket. The MM-GBSA studies were performed for all synthesized derivatives and among them, compound 3-(4-Chlorophenyl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 5f, showed the lowest the binding free energy (-48.04 kcal mol-1). In general, oxazine derivatives could be proposed as the strong AChE inhibitors.

Synthesis and Biological Evaluation of New Compounds with Nitroimidazole Moiety.

Heterocyclic compounds, particularly those containing azole rings, have shown extensive biological activity, including anticancer, antibacterial, and antifungal properties. Among these, the imidazole ring stands out due to its diverse therapeutic potential. In the presented study, we designed and synthesized a series of imidazole derivatives to identify compounds with high biological potential. We focused on two groups: thiosemicarbazide derivatives and hydrazone derivatives. We synthesized these compounds using conventional methods and confirmed their structures via nuclear magnetic resonance spectroscopy (NMR), MS, and elemental analysis, and then assessed their antibacterial and antifungal activities in vitro using the broth microdilution method against Gram-positive and Gram-negative bacteria, as well as Candida spp. strains. Our results showed that thiosemicarbazide derivatives exhibited varied activity against Gram-positive bacteria, with MIC values ranging from 31.25 to 1000 µg/mL. The hydrazone derivatives, however, did not display significant antibacterial activity. These findings suggest that structural modifications can significantly influence the antimicrobial efficacy of imidazole derivatives, highlighting the potential of thiosemicarbazide derivatives as promising candidates for further development in antibacterial therapies. Additionally, the cytotoxic activity against four cancer cell lines was evaluated. Two derivatives of hydrazide-hydrazone showed moderate anticancer activity.