Introduction: Diabetes mellitus (DM) is a chronic metabolic disorder characterized by impaired wound healing. The goal of this study was to create and assess Schiff base derivatives (SB) of L-arginine and aromatic aldehydes as possible inhibitors of nitric oxide synthase (NOS). Materials and Methods: Synthesis of SB derivatives was followed by ADMET analysis and molecular docking against the NOS protein (PDB ID: 4NOS, 2.25 Å resolution) obtained from the RCSB Protein Data Bank. Structure-activity correlations were established, and NOS inhibitory activity was evaluated in vitro. Result: FTIR and 1H NMR spectroscopy were used to characterize the five most promising derivatives (CM7, CM8, CM9, CM11, and CM14), which were produced utilizing L-arginine and aromatic natural aldehydes in ethanol/methanol solvents. High binding affinities for CM8 (-9.0 kcal/mol), CM9 (-8.8 kcal/mol), and CM11 (-9.1 kcal/mol) were found via molecular docking. Discussion: The compounds met all pharmacokinetic ADME and toxicity criteria and demonstrated NOS inhibitory action on par with the standard. In order to improve wound healing in diabetics, this study presents L-arginine Schiff base derivatives, a novel class of NOS inhibitors. Conclusion: This research introduces L-Arginine Schiff base (SB) derivatives as a potential class of Nitrous oxide inhibitors that have remained elusive until now.
In the original publication [1], Figure 2 was published incompletely due to a formatting error, resulting in a portion of the visual data being cut off. The complete and correct Figure 2 is provided below. This correction does not alter the scientific findings, results, or conclusions of the article. We regret the error and apologise to the readers. The original article can be found online at: https://www.benthamscience.com/article/155090
Abstract: The Morita–Baylis–Hillman (MBH) reaction is one of the most powerful and versatile organocatalytic transformations for constructing carbon–carbon, carbon–nitrogen, and carbon– sulphur bonds. Owing to its high atom economy and operational simplicity, the MBH reaction has found widespread applications in the synthesis of heterocyclic frameworks, biologically active molecules, and key intermediates for pharmaceuticals and functional materials. Among various MBH substrates, nitroallylic MBH adducts derived from β-nitrostyrene have gained significant attention due to their unique electronic properties and multifaceted reactivity. The presence of a strong electron-withdrawing nitro group in conjunction with an allylic alcohol moiety renders these adducts highly reactive and tunable intermediates. This review comprehensively summarizes recent advances in the diversified functionalization of nitroallylic MBH acetates, with a particular emphasis on their application in the construction of structurally diverse heterocyclic compounds. A wide range of heterocycles, including furan derivatives, naphthopyrans, pyrazoles, imidazoles, imidazo[ 1,2-a]pyridines, pyrroles, benzimidazothiazines, benzimidazothiazoles, dihydroazopyrimidines, indolizines, 6-(2-hydroxyaryl)picolinates, meta-terphenyls, 4,6-diarylpicolinates, 2-aryl terephthalates, diazepinones, benzo[b][1,6]naphtho[2,3-d]oxazocin-2-ones, and tetrahydrospiropyrans are discussed in detail. β-Nitrostyrene, readily prepared via a simple nitro-aldol reaction, serves as an ideal activated olefin for MBH reactions with various electrophiles. This review highlights the reactions of β-nitrostyrene with aldehydes and ethyl glyoxalate to afford the corresponding MBH adducts. In comparison, reactions with prochiral electrophiles such as formaldehyde generate primary MBH alcohols; reactions with ethyl glyoxalate yield secondary MBH alcohols. The synthetic utility of these MBH alcohols as 1,4-ambiphiles is critically examined. Furthermore, transformations at the chiral center, including conversion to acetate (–OAc) and arylamino (–NH– Ar) functionalities, are elaborated. Collectively, the diverse reactivity of β-nitrostyrene-derived MBH adducts as electrophiles, bis-electrophiles, and ambiphiles is systematically covered, highlighting their strategic importance in modern synthetic organic chemistry. This review is expected to inspire the development of new and efficient synthetic protocols exploiting this emerging and versatile class of MBH adducts.
Introduction Coumarin derivatives exhibit significant biological and pharmacological activities, motivating the design of new coumarin-based compounds. This study aimed to synthesize novel coumarin-3-carboxamides using a simple and efficient multicomponent reaction, and to investigate their structural and electronic properties through theoretical calculations. Quantum theoretical studies on compounds 4a, 4b, and 4c were performed at the B3LYP level of theory with the 6-311+G** basis set. The optimized geometric parameters were compared with experimental data. The structure of the compounds was confirmed by IR, 1 H NMR, 13C NMR, and elemental analysis. Further computational analyses were conducted to predict the IR spectra, 1 H NMR, and 13 C NMR chemical shifts in the ground state. The study also included an examination of the frontier molecular orbitals (FMOs), total density of states (DOS), and thermodynamic parameters. The theoretical and experimental results demonstrated excellent agreement, confirming the reliability of the computational models used.Methods The target coumarin-3-carboxamides were synthesized via a three-component condensation of salicylaldehyde derivatives, diethyl malonate, and N-aminophthalimide in refluxing ethanol, catalyzed by iodine and piperidine. The structures of the synthesized compounds were confirmed using IR spectroscopy, 1H and 13C NMR, and elemental analysis. Quantum chemical calculations were performed at the B3LYP/6-311+G** level to optimize geometric parameters, predict IR and NMR spectra, and analyze frontier molecular orbitals (FMOs), density of states (DOS), and thermodynamic properties.Results The synthesis proceeded with good yields, and experimental characterization confirmed the proposed structures. Theoretical calculations showed excellent agreement with experimental data, validating the computational models. FMOs and DOS analyses provided insight into electronic distributions and stability, while predicted spectroscopic properties closely matched the measured spectra.Discussion The combination of experimental and computational results allowed a comprehensive understanding of the structural and electronic characteristics of the synthesized coumarin-3-carboxamides. These findings highlight the reliability of the chosen theoretical methods and suggest potential applicability of these compounds in further chemical and pharmaceutical research.Conclusion A convenient method for synthesizing coumarin-3-carboxamides was established, and theoretical studies successfully complemented experimental findings. The integrated approach confirms the structural integrity and electronic features of the compounds, providing a foundation for future exploration of their properties and applications.
Introduction: Tetraarylethene and triarylethene derivatives are important structural motifs in functional materials, particularly as Aggregation-Induced Emission (AIE) luminogens. Conventional synthetic strategies for AIEgens typically rely on McMurry coupling or palladiumcatalyzed cross-coupling reactions involving boronic alkene derivatives with aryl bromides and/or alkynes, which often face challenges regarding stereochemical selectivity Methods: Herein, we report the direct synthesis of tetraarylethene and triarylethene via a practical one-step palladium(0)-catalyzed Suzuki-Miyaura cross-coupling reaction. The optimization protocol utilized commercially available, inexpensive starting substrates, specifically tetrachloroethene and trichloroethene, reacting with various aryl boronic acids under optimized catalytic conditions. Results: The target multi-arylated ethenes were successfully synthesized in a single step for the first time. The methodology demonstrated broad functional-group tolerance, affording all desired compounds in moderate to good yields. The synthesized structures were fully isolated and characterized by 1 H NMR and 13C NMR spectroscopy. Discussion: Compared with conventional strategies that inherently require tedious multistep synthesis, this developed approach provides a significantly more direct, rapid, and efficient route to access multi-arylated ethene derivatives by successfully activating the generally unreactive carbonchlorine bonds. Conclusion: This established protocol provides a convenient and highly efficient synthetic route to tetraarylethene and triarylethene scaffolds from inexpensive, readily available industrial chemicals, offering strong potential for future AIE-materials development.
