Search Results (90)

The BODIPY core has emerged as a versatile scaffold for the design of photoremovable protecting groups (PPGs). Herein, we report the synthesis of a novel BODIPY–epinephrine conjugate linked via a carbamate moiety, enabling light-triggered release of the active compound (epinephrine, also known as adrenaline). The structure of the obtained product was confirmed by ¹H and M ¹³C NMR spectroscopy as well as high-resolution mass spectrometry (HRMS). The described conjugate represents a potential tool for the photoactivated modulation of biologically relevant processes. Full article

In this study, a comprehensive derivatization strategy for biogenic amines based on the formation of volatile carbamate derivatives using 2,2,2-trifluoroethyl chloroformate (TFECF) was successfully developed and evaluated. A series of biogenic amine derivatives was obtained in excellent yields (94–99%) and structurally confirmed using NMR, MS, and crystal structure analysis. The reagent demonstrated high reactivity toward primary and secondary amines, providing derivatives of excellent purity and satisfactory volatility. The applicability of the proposed procedure to real food matrices was demonstrated using GC-MS. The obtained results were compared with the corresponding ethyl chloroformate (ECF) derivatives. TFECF derivatives exhibited significantly improved volatility, reflected in shorter retention times and enhanced analytical performance. Full article

The exploitation of natural products as lead compounds continues to serve as a vital strategy for the discovery of novel fungicidal agents. This work designed and synthesized a series of carbamate derivatives based on the natural product physostigmine and commercial carbamate fungicides. The title compounds were synthesized from readily available aromatic aldehydes via green Curtius rearrangement. The antifungal activities of those compounds were evaluated in vitro against eight phytopathogenic fungi. Many of the carbamate compounds exhibited good fungicidal activities. Among those molecules, compounds 3a9, 3b1, 3b2 and 3b12 outperformed the potency of the positive control azoxystrobin against certain fungi. Moreover, compounds 3b2, 3b3, and 3b12 showed outstanding and broad-spectrum in vitro antifungal activities against seven fungi with an inhibition rate of over 70% at 50 μg/mL. The preliminary structure-activity relationship (SAR) investigations demonstrated that N-aryl carbamates bearing a chlorine atom(s) or two bromine atoms on the di-substituted phenyl ring showed superior antifungal potency. This work might lay the foundation for investigating natural-source-based green fungicides, which exhibited great potential as novel antifungal lead compounds. Full article

(This paper presents the synthesis of a novel copper(II) metal complex with ethyl (2-(methylcarbamoyl)phenyl)carbamate and 3-methylquinazoline-2,4(1H,3H)-dione. The characterization of the compound was conducted through various techniques, including melting point determination, microwave plasma atomic emission spectrometry (MP-AES) for Cu, attenuated total reflection (ATR), IR, ¹H NMR, and ¹³C NMR spectroscopy. The coordination compound was obtained after mixing water solutions of the metal salt and the ligand dissolved in DMSO and water solutions of NaOH, in a metal-to-ligand-to-base ratio of 1:2:2. The ligand and the metal chloride were brought into the reaction at room temperature in DMSO and H₂O as solvents, respectively. The results indicate the successful formation of a stable mixed-ligand Cu(II) coordination compound involving N,O-donor ligands. Based on the obtained data, we assumed that the ligands are coordinated through N- and O-donor atoms. Spectroscopic data suggested that the ligand (3-methylquinazoline-2,4(1H,3H)-dione), by using (NaOH), coordinated to a metal ion as a monodentate ligand through the nitrogen atom of the NH group and ethyl (2-(methylcarbamoyl)phenyl)carbamate coordinated in a bidentate fashion through the N- and O-donor atoms of ester group. Additionally, two hydroxyl groups were bridged for two metal ions into the formed dimer structure. Full article

Heterocycles—cyclic compounds containing at least one non-carbon heteroatom (e.g., N, O, S)—are fundamental in medicinal chemistry due to their influence on a drug’s physicochemical and biological properties. They improve solubility, bioavailability, and facilitate molecular recognition through their electronic and hydrogen-bonding features. These properties make them indispensable in drug design. This study focuses on the synthesis of a key heterocyclic intermediate: benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate. This molecule incorporates a thiazole ring, known for its rigidity and electronic properties, that enhances target interactions. The 2-position bears a Cbz-protected amine, enabling orthogonal deprotection, while the 4-position features a hydroxyethyl side chain, providing a handle for further chemical modifications via nucleophilic substitution. Herein, we report the successful synthesis of this intermediate along with its full ¹H and ¹³C NMR spectra, melting point, and crystal structure, confirming its identity and purity. Full article

This manuscript reports the synthesis and characterization of 19 novel heterostilbene carbamates, designed as selective butyrylcholinesterase (BChE) inhibitors with potential applications in the treatment of neurodegenerative disorders, particularly Alzheimer’s disease. The compounds were synthesized from resveratrol analogs, and their structures were confirmed by NMR spectroscopy, high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction for selected derivatives (compounds 1 and 4). In vitro assays demonstrated high selectivity toward BChE over acetylcholinesterase (AChE), with compound 16 exhibiting exceptional inhibitory activity (IC₅₀ = 26.5 nM). Furthermore, compound 16 showed moderate anti-inflammatory effects by inhibiting LPS-stimulated TNF-α production in peripheral blood mononuclear cells. In silico ADME(T) profiling revealed favorable pharmacokinetic properties and low mutagenic potential for the majority of compounds. Molecular docking and molecular dynamics simulations confirmed stable binding interactions within the BChE active site. These results highlight heterostilbene carbamates as promising lead structures for developing novel therapeutic agents targeting neurodegenerative diseases. Full article

Background: Indoor residual spraying (IRS) is a core insecticide-based vector control tool employed in most malaria-affected settings globally. However, mosquito vectors have developed resistance to nearly all of the insecticides currently used in IRS. This has necessitated a transition to new classes of insecticides, from mostly using dichlorodiphenyltrichloroethane (DDT) and pyrethroids from 1997 to 2010 to carbamates in 2011 and organophosphates in 2013. In addition, other vector control measures, like the use of long-lasting insecticide-treated bed nets (LLINs), have also been employed for malaria control. Despite the implementation of these mosquito vector control interventions, malaria remains a disease of public health concern, especially in sub-Saharan Africa, which bears over 90% of the disease burden. This review will thus collate evidence on the effectiveness of IRS for malaria control in sub-Saharan Africa. Methods and analysis: The systematic review will be conducted following a priori criteria developed using the PRISMA guidelines. Articles will be obtained through a search of the Web of Science, Google Scholar, Medline via PubMed, Scopus and Embase databases. Mesh terms and Boolean operators (“AND”, “OR”) will be used in the article search. Additionally, websites of malaria research institutions will be searched. The article search will be conducted by two independent librarians (AAK and RS). All identified articles will be transferred to EPPI-reviewer v6.15.1.0 software. Article screening and data abstraction will be performed in duplicate by four reviewers (KOO, LN, GK and MO), and any further disagreements will be resolved through discussion and consensus. We shall extract data on the country, region, study design, insecticide combination, season, susceptibility procedure used, vector control interventions, population, mosquito species, malaria incidence or prevalence, insecticide efficacy, susceptibility, genotypic resistance, vector mortality and knockdown effect. Data analysis will be performed using STATA v17.0. Effect sizes will be statistically pooled using inverse-variance-weighted random-effects meta-analysis. Heterogeneity and publication bias in the articles will be assessed using the I² statistic and a funnel plot, respectively. For the studies that will not be included in the meta-analysis, a narrative synthesis will be written following the Cochrane Consumer and Communication Review Group format. Results: The findings of this review will help generate evidence on the effectiveness of indoor residual spraying using WHO pre-qualified insecticides in malaria control in sub-Saharan Africa. This protocol was registered in PROSPERO, registration number CRD42024517119. Full article

The formation of (R)-methyl-(2-hydroxy-1-phenylethyl)carbamate through Pd(PPh₃)₄-catalyzed synthesis was investigated using computational methods to elucidate the reaction pathway and energetic feasibility. Density functional theory (DFT) calculations confirmed that the direct reaction between (R)-(-)-2-phenylglycinol and methyl chloroformate is not spontaneous, requiring a catalyst to proceed efficiently. The study proposes a detailed mechanistic pathway involving ligand dissociation, intermediate formation, and hydrogenation. The role of Pd(PPh₃)₄ was examined, demonstrating its ability to stabilize reaction intermediates and facilitate key transformations, such as dehydrogenation and chlorine elimination. Two reaction pathways were identified, with Pathway 1 exhibiting a net energy of –84.7 kcal/mol and Pathway 2 showing an initial positive energy of 90.1 kcal/mol. However, the regeneration of key intermediates in Pathway 2 ultimately reduces the total reaction energy to –238.7 kcal/mol, confirming the feasibility of both routes. Computational results align with experimental NMR data, supporting the formation of the proposed intermediates. These findings provide valuable insights into catalyst optimization, suggesting that ligand modifications or alternative palladium-based catalysts could enhance efficiency. This study advances the understanding of Pd-catalyzed carbamate synthesis and offers a basis for future experimental and computational investigations. Full article

Ethyl carbamate (EC), known as urethane, is a naturally occurring potentially carcinogenic metabolite that is widely found in alcoholic beverages and other food-related fermented products. The concern related to the presence of the EC and its toxicity in regularly consumed fermented alcoholic beverages raises global interest in assessing the possible risks to human health. EC mitigation approaches, such as molecular imprinting technology (MIT), have been proposed to target EC while preserving the sensory quality of fermented alcoholic beverages. This review explores the principles of MIT, the advantages and disadvantages of the most common polymerisation approach for molecularly imprinted polymer (MIP) synthesis, the analytical techniques used for MIP characterisation, and the strategies used to mitigate EC in fermented alcoholic beverages, with studies reporting removal efficiencies of up to 84%. Additionally, it highlights the novelty and potential of MIPs, offering practical insights into their integration within the production of fermented alcoholic beverages, highlighting their scalability and cost-effectiveness compared to traditional EC mitigation strategies. Full article

This study presents the synthesis of allyl-functionalized polysaccharide carbamates (AFCs) with tailored water solubility designed for use in responsive hydrogels and 3D printing applications. A modular one-pot approach was employed to produce cellulose- and xylan-based AFCs, utilizing polysaccharide phenyl carbonates as activated compounds. By fine-tuning the degree of substitution (DS) of functional groups, the water solubility and shear-thinning properties of AFCs were controlled to enhance the gelation and printability. AFC-based hydrogels could be obtained by rapid gelation induced without harmful catalysts through UV irradiation at 365 nm. The materials displayed highly porous and interconnected microstructures, as well as mechanical resilience and high swelling ratios. The hydrogel formation was characterized, and its crosslinking degree was calculated using HR-MAS NMR. The study demonstrated that gelation behavior was sensitive to the pH value, with optimal results under neutral or acidic conditions. Initial 3D printing trials confirmed the material’s rapid shaping capabilities, which is beneficial for biomedical applications and advanced manufacturing of stimuli-responsive materials. Full article

Considering our previous experience in the design of new cholinesterase inhibitors, especially resveratrol analogs, in this research, the basic stilbene skeleton was used as a structural unit for new carbamates designed as potentially highly selective butyrylcholinesterase (BChE) inhibitors with excellent absorption, distribution, metabolism, excretion and toxicity ADMET properties. The inhibitory activity of newly prepared carbamates 1–13 was tested toward the enzymes acetylcholinesterase (AChE) and BChE. In the tested group of compounds, the leading inhibitors were 1 and 7, which achieved excellent selective inhibitory activity for BChE with IC₅₀ values of 0.12 ± 0.09 μM and 0.38 ± 0.01 μM, respectively. Both were much more active than the standard inhibitor galantamine against BChE. Molecular docking of the most promising inhibitor candidates, compounds 1 and 7, revealed that stabilizing interactions between the active site residues of BChE and the ligands involve π-stacking, alkyl-π interactions, and, when the carbamate orientation allows, H-bond formation. MD analysis confirmed the stability of the obtained complexes. Some bioactive resveratrol-based carbamates displayed complex-forming capabilities with Fe³⁺ ions as metal centers. Spectrophotometric investigation indicated that they coordinate one or two metal ions, which is in accordance with their chemical structure, offering two binding sites: an amine and a carboxylic group in the carbamate moiety. Based on the obtained in silico, experimental and computational results on biological activity in the present work, new carbamates 1 and 7 represent potential selective BChE inhibitors as new therapeutics for neurological disorders. Full article

One of the major challenges in gene therapy is the efficient and safe introduction of nucleic acids into eukaryotic cells. This process requires overcoming various biological barriers and navigating complex pathways to reach target cells and achieve their biological function. To address this obstacle, numerous transfection methods have been developed, including physical techniques and the use of genetic vectors, both viral and non-viral. However, to date, no transfection method is 100% safe and efficient. Within the spectrum of non-viral genetic vectors, cationic liposomes formed by cationic lipids stand out for their ability to protect and deliver therapeutic NA. These liposomes offer greater biocompatibility and lower immunogenicity compared to viral vectors, although they still do not match the efficiency of viral delivery systems. Consequently, ongoing research focuses on synthesizing a wide variety of cationic lipids in the search for compounds that provide high transfection efficiency with minimal cytotoxicity. This study aimed to design and synthesize a novel cationic lipid (CholCadLys) derived from natural cellular molecules for transferring genetic material to eukaryotic cells. The lipid was synthesized using cholesteryl chloroformate for the hydrophobic region, cadaverine as a linker, and lysine for the polar region, connected by carbamate and amide bonds, respectively. Identification was confirmed through thin-layer chromatography, purification through preparative chromatography, and characterization via infrared spectroscopy and mass spectrometry. The synthesis yielded a 60% success rate, with stable nanoliposomes averaging 76 nm in diameter. Liposomes were formed using this CL and commercial neutral lipids, characterized by transmission electron microscopy and Nanoparticle Tracking Analysis. These liposomes, combined with plasmid DNA, formed lipoplexes used to transfect Hek-293 FT cells, achieving up to 40% transfection efficiency without cytotoxicity in the mixture of CholCadLys and CholCad. This novel CL demonstrates potential as an efficient, safe, and cost-effective gene transfer system, facilitating further development in gene therapy. Full article

Herein, a novel glycidyl carbamate functional epoxy resin (GCE) is synthesized by the additional reaction of the isocyanate group of tolylene diisocyanate (TDI) with the hydroxyl group of hydroxyl-terminated polybutadiene (HTPB) and glycidol. The successful synthesis of the GCE is confirmed by FT-IR and ¹H NMR spectroscopy. Furthermore, a dual-curing adhesive system is developed using acrylic acid and trimethylolpropane triacrylate with varying GCE contents, and its adhesive performance is assessed by testing adhesive strength, pencil hardness, and surface energy. As a result, the dual-cure adhesive containing 0.2 mol of GCE demonstrates an impressive adhesive strength of 11.1 MPa, a pencil hardness of B, and surface energy comparable to that of standard polycarbonate film. Full article

The application of immobilized enzymes often plays a key role in successfully implementing an economically feasible biocatalytic process at an industrial scale. Designing an immobilized biocatalyst involves solving several tasks, from the selection of the carrier and immobilization method to the characterization of the kinetic properties of the immobilized enzyme. In this study, we focused on the kinetic properties of free and immobilized ß-N-acetylhexosaminidase (Hex), a promising enzyme for application in the field of biotechnology, especially for the synthesis of bioactive carbohydrates. Hex was immobilized via covalent binding in methacrylate particles. The effect of immobilizing Hex from Penicillium oxalicum into porous particles on kinetic properties was investigated, and mathematical and experimental modeling showed that the kinetic behavior of the enzyme was significantly influenced by diffusion in the particles. Along with the study on kinetics, a simple method was developed to investigate the reversible inhibition of the immobilized enzyme in a continuous-flow system. The method is suitable for application in cases where a chromogenic substrate is used, and here it was applied to demonstrate the inhibitory effects of N-acetyl-glucosaminyl thiazoline (NAG-thiazoline) and O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate ((Z)-PugNAc) on Hex. Full article

Urethane surfactants (REQ) were synthesized with octadecanol ethoxylate (AEO) and isocyanate methacrylate (IEM). Subsequently, reactive-carbamate-surfactant-modified nanomicrospheres (PER) were prepared via two-phase aqueous dispersion polymerization using acrylamide (AM), 2-acrylamido-2-methylpropanesulfonic acid (AMPS) and ethylene glycol dimethacrylate (EGDMA). The microstructures and properties of the nanomicrospheres were characterized and examined via infrared spectroscopy, nano-laser particle size analysis, scanning electron microscopy, and in-house simulated exfoliation experiments. The results showed that the synthesized PER nanomicrospheres had a uniform particle size distribution, with an average size of 336 nm. The thermal decomposition temperature of the nanomicrospheres was 278 °C, and the nanomicrospheres had good thermal stability. At the same time, the nanomicrospheres maintained good swelling properties at mineralization < 10,000 mg/L and temperature < 90 °C. Under the condition of certain permeability, the blocking rate and drag coefficient gradually increased with increasing polymer microsphere concentration. Furthermore, at certain polymer microsphere concentrations, the blocking rate and drag coefficient gradually decreased with increasing core permeability. The experimental results indicate that nanomicrospheres used in the artificial core simulation drive have a better ability to drive oil recovery. Compared with AM microspheres (without REQ modification), nanomicrospheres exert a more considerable effect on recovery improvement. Compared with the water drive stage, the final recovery rate after the drive increases by 23.53%. This improvement is attributed to the unique structural design of the nanorods, which can form a thin film at the oil–water–rock interface and promote oil emulsification and stripping. In conclusion, PER nanomicrospheres can effectively control the fluid dynamics within the reservoir, reduce the loss of oil and gas resources, and improve the economic benefits of oil and gas fields, giving them a good application prospect. Full article