77Se NMR Research Articles

Studies on the Effect of Positive and Negative Charges on the 77Se NMR Shifts of Selenones and Selenenyls of N-heterocyclic Carbenes of Imidazolium-4,5-dicarboxylates.

1,3-Imidazole-4,5-dicarboxylic acid derivatives were investigated with respect to the properties of the underlying N-heterocyclic carbenes. Their selenium adducts were prepared as diesters, monoesters, and dianionic dicarboxylates. Se-methylation yielded selenenyls (cationic selenoethers). 77Se NMR shifts of selenium adducts are considered a measure of the electronic properties of the underlying N-heterocyclic carbene. Since they are very sensitive to external (solvent, pH, temperature, reference reagent, reference method) and internal parameters (substituent effects, steric effects, nonclassical H-bonding, anisotropy), difficulties can arise in reliably interpreting these values. Our model compounds allow the systematic investigation of the influence of charges on the 77Se NMR shifts since both structural changes and changes of the measurement conditions have been minimized. Depending on the charge, the 77Se NMR shifts cover the range from 42.1 ppm (dianionic dicarboxylate) via 65.0 ppm (monoanionic dicarboxylate) and 92.5 ppm (neutral diester) to 153.8 ppm (cationic selenoether) in DMSO-d6. The signals also show considerable solvent and pH dependence, which was investigated with a selection of NMR solvents (MeOD, CDCl3, CD2Cl2, CD3COOD, CD3CN, acetone-d6, THF-d8, pyridine-d5, toluene-d8, DMSO-d6) and pH values in D2O. Linear relationships were found between the HOMO and LUMO energies and the 77Se NMR shifts, respectively.

Synthesis of [Fe2[(μ-SeCH2)2NH](CN)2(CO)4]2- and Related Iron Selenoates.

The dianion [Fe2[(μ-SeCH2)2NH](CN)2(CO)4]2- ([2]2-) is of interest for the preparation of the selenide analog of the active site of the [FeFe]-hydrogenases. The obvious route for its synthesis by cyanation of Fe2[(μ-SeCH2)2NH](CO)6 (3) fails for reasons that this paper explains and resolves. We show that CN- cleaves Se-C bonds in 3. For example, treatment of Fe2[(μ-SeCH2)2NH](CO)6 with NEt4CN followed by CH3I gives substantial amounts of Fe2(μ-SeCH3)2(CO)6. Authentic [2]2- can be obtained by cyanation of Fe2[(μ-SeCH2)2NH](CO)5(pyridine). The 77Se NMR data for [2]2- and 3 are reevaluated and explained. Attempts to prepare Fe2[(μ-SeCH2)2NH](PPh3)2(CO)4 (9) by Me3NO-induced decarbonylation of 3 also suffers from degradation of the organoselenium ligand. Complex 9 was prepared instead by photosubstitution. The protonation of [2]2- and [Fe2[(μ-SCH2)2NH](CN)2(CO)4]2- are compared: the selenium compounds are more basic. The structure of [HFe2[(μ-SCH2)2NH](CN)2(CO)4]- was determined crystallographically.

Phosphorus Oxidation Controls Epitaxial Shell Growth in InP/ZnSe Quantum Dots.

InP/ZnSe/ZnS core/shell/shell quantum dots are the most investigated quantum dot material for commercial applications involving visible light emission. The inner InP/ZnSe interface is complex since it is not charge balanced, and the InP surface is prone to oxidation. The role of oxidative defects at this interface has remained a topic of debate, with conflicting reports of both detrimental and beneficial effects on the quantum dot properties. In this study we probe the structure of the InP/ZnSe interface at the atomic level using 31P, 77Se and 17O ssNMR and HAADF-STEM. We observe clear differences in Se NMR spectra and crystal orientation of core and shell when the InP/ZnSe is oxidized on purpose. High levels of interface oxidation result in an amorphous phosphate layer at the interface, which inhibits epitaxial growth of the ZnSe shell.

Greening the Synthesis of 2,3‐Dihydrobenzofuran Selenides: I2/TBHP‐Promoted Selenocyclization of 2‐Allylphenols

In this work we describe the synthesis of selenium‐containing dihydrobenzofurans through the selenocyclization reaction of 2‐allylphenols. The reaction procedure uses only an I2/TBHP oxidant system at room temperature, enabling an efficient synthesis of 2‐[(organoselanyl)methyl]‐2,3‐dihydrobenzofurans. The products are formed immediately after the addition of the oxidant system in a mixture of 2‐allylphenol and diorganyl diselenide, in the absence of solvent, at mild experimental conditions. Furthermore, control experiments were carried out, including 77Se NMR analyses to identify intermediates, which contributed to the elucidation of the reaction mechanism.

Design, Synthesis, and Antibacterial Activities of Multi-Functional C2-Functionalized 1,4-Naphthoquinonyl Organoseleniums.

A practical and efficient reaction for C2-selenylation of 1,4-naphthoquinones has been explored. This coupling reaction of two redox structural motifs, such as 2-bromo-1,4-naphthoquinone with diaryldiselenide/ebselen has been achieved by using sodium borohydride reducing agent at room temperature. Using this approach, several 2-selenylated-1,4-naphthoquinones were obtained in moderate to good yields and thoroughly characterized by multinuclear (1H, 13C, and 77Se) NMR, cyclic voltammetry, and mass spectrometry. Further, light-irradiated thiolation of the synthesized selenazinone was also performed to show the utility of the synthesized compound for post-functionalization. Several 2-selenylated-1,4-naphthoquinones were studied by SC-XRD in which intramolecular Se⋅⋅⋅N (from quinolinyl ligand) non-bonded interactions were observed. Photophysical studies (UV-visible, emission, solvatochromism, and quantum yield) were also performed on selected C2-selenylated naphthoquinones. The naphthoquinonyl organoseleniums were also screened for their antibacterial properties and quinonyl organoselenium 5 d shows good antibacterial potential against S. aureus ATCC 29213 with MIC 0.5 μg/mL and a Selectivity Index of >200. Moreover, it also exhibited equipotent activity against various strains of S. aureus and Enterococcus faecium, including strains resistant to vancomycin and meropenem. From structure-activity correlation, it seems that nice blend of oxidant properties from quinone and antioxidant properties from selenium moiety makes it better candidate for antibacterial activity.

Bipyridyl Functionalized NHC-Sulfenyl, Selenenyl Cations; Potential Species for Alkylation Reactions and Ligands in Copper(I) Catalysis.

Reactions of bipyridyl-functionalized imidazole-thiones and selones with MeX (X=I, OTf) afforded sulfenyl and selenenyl cations [(NNC)EMe]X (2/3, E=S, Se). Further reactions of these main-group cations with [Cu(CH3CN)4]BF4, Cu(OTf) furnished dicationic [{Cu(μ-I)(NNC)EMe}2][Y]2 (5/6, Y=BF4, OTf) and tricationic copper(I) complexes [Cu{(NNC)EMe}2](OTf)2BF4 (7 a/7 b) when employed [(NNC)EMe]I and [(NNC)EMe]OTf respectively. All these cationic complexes were characterized by various spectroscopic techniques, including X-ray diffraction analysis. The solid-state structures revealed novel bonding modes of the cations. The cationic nature of new complexes was analyzed by the 77Se NMR spectroscopy, which indicated different electronic environments around the selenium centers. The cations [(NNC)EMe]X (X= I, OTf), and (NNC)SMe bearing copper complex [{Cu(μ-I)(NNC)EMe}2][Y]2 proved as potential candidates for alkylation of various Lewis bases and as molecular catalyst in aldehyde-alkyne-amine coupling reactions, respectively. The latter catalytic reactions yielded a range of three-component products in good to excellent yields with low catalyst loading under solvent-free conditions, which demonstrate the potential utility of group-16 cations as ancillary ligands in homogeneous catalysis.

Host-Guest Interactions Facilitated by Chalcogen Bonding within Selenadiazole Functionalised Porphyrin Nanotubes.

The structural rigidity of tetrakis(4-pyridyl)porphyrin (TPyP) has been utilised to prepare a robust novel porous coordination polymer of composition Cd2(TPyP)(sez)2 (TPyP=5,10,15,20-tetra(4-pyridyl)porphyrin, sez=1,2,5-benzoselenadiazole-5-carboxylate). The coordination polymer may be described as a hexagonal porphyrin nanotube (PNT) and has the potential to bind guest molecules through chalcogen bonding. Single crystal X-ray diffraction (SCXRD) data indicate an internal pore diameter ~9 Å which represents ~35 % of the crystal volume. Immersion of the PNTs in solvents such as DMSO and CS2 result in the incorporation of these molecules within the nanotubes with chalcogen bonding between host and guest. The crystallographic guest-inclusion investigations are complemented by solid-state 77Se, 13C, 113Cd and 2H NMR studies which provide insights into dynamic behaviour. The porosity of the crystals was further explored using gas adsorption experiments, indicating the reversible uptake of CO2, CH4, H2 and N2. Structure-function relationships are clearly established from complementary crystallographic, NMR and adsorption investigations.

Structures of a DNA Polymerase Caught while Incorporating Responsive Dual-Functional Nucleotide Probes.

Functionalizing nucleic acids using DNA polymerases is essential in biophysical and biotechnology applications. This study focuses on understanding how DNA polymerases recognize and incorporate nucleotides with diverse chemical modifications, aiming to develop advanced nucleotide probes. We present the crystal structures of ternary complexes of Thermus aquaticus DNA polymerase (KlenTaq) with C5-heterocycle-modified environment-sensitive 2'-deoxyuridine-5'-triphosphate (dUTP) probes. These nucleotides include SedUTP, BFdUTP and FBFdUTP, which bear selenophene, benzofuran and fluorobenzofuran, respectively, at the C5 position of uracil, and exhibit high conformational sensitivity. SedUTP and FBFdUTP serve as dual-app probes, combining a fluorophore with X-ray anomalous scattering Se or 19F NMR labels. Our study reveals that the size of the heterocycle influences how DNA polymerase families A and B incorporate these modified nucleotides during single nucleotide incorporation and primer extension reactions. Remarkably, the responsiveness of FBFdUTP enabled real-time monitoring of the binary complex formation and polymerase activity through fluorescence and 19F NMR spectroscopy. Comparative analysis of incorporation profiles, fluorescence, 19F NMR data, and crystal structures of ternary complexes highlights the plasticity of the enzyme. Key insight is provided into the role of gatekeeper amino acids (Arg660 and Arg587) in accommodating and processing these modified substrates, offering a structural basis for next-generation nucleotide probe development.

Structures of a DNA Polymerase Caught while Incorporating Responsive Dual‐Functional Nucleotide Probes

Functionalizing nucleic acids using DNA polymerases is essential in biophysical and biotechnology applications. This study focuses on understanding how DNA polymerases recognize and incorporate nucleotides with diverse chemical modifications, aiming to develop advanced nucleotide probes. We present the crystal structures of ternary complexes of Thermus aquaticus DNA polymerase (KlenTaq) with C5‐heterocycle‐modified environment‐sensitive 2′‐deoxyuridine‐5′‐triphosphate (dUTP) probes. These nucleotides include SedUTP, BFdUTP and FBFdUTP, which bear selenophene, benzofuran and fluorobenzofuran, respectively, at the C5 position of uracil, and exhibit high conformational sensitivity. SedUTP and FBFdUTP serve as dual‐app probes, combining a fluorophore with X‐ray anomalous scattering Se or 19F NMR labels. Our study reveals that the size of the heterocycle influences how DNA polymerase families A and B incorporate these modified nucleotides during single nucleotide incorporation and primer extension reactions. Remarkably, FBFdUTP's responsiveness enabled real‐time monitoring of the binary complex formation and polymerase activity through fluorescence and 19F NMR. Comparative analysis of incorporation profiles, fluorescence, 19F NMR data, and crystal structures of ternary complexes highlights the enzyme's plasticity. Key insights are provided into the role of gatekeeper amino acids (Arg660 and Arg587) in accommodating and processing these modified substrates, offering a structural basis for next‐generation nucleotide probe development.

Anionic N-Heterocyclic Carbenes from Mesoionic Imidazolium-4-pyrrolides: The Influence of Substituents, Solvents, and Charge on their 77Se NMR Chemical Shifts.

Mesoionic compounds are the starting material for the synthesis of unique anionic N-heterocyclic carbenes. Herein, mesoionic imidazolium pyrrolides synthesized from pyrrole-2-carbaldehyde via various N-alkyl-4-pyrroyl-imidazoles are described. These were converted into nine new 4-(pyrrol-2-yl)-substituted imidazolium salts and transformed into the mesoionic title compounds using an anion exchange resin. The DFT-calculated (B3LYP/6-311++G**) CREF values indicate a great potential for the formation of anionic N-heterocyclic carbenes by deprotonation, which were generated and reacted with selenium to obtain selenoureas. The 77Se NMR shifts investigated under systematic variation of conditions are dependent on the substitution pattern (ΔδSe = 133 ppm) and the steric demand of the substituents. Solvent dependencies of the 77Se NMR shifts were investigated applying toluene-d8, THF-d8, CDCl3, CD2Cl2, pyridine-d5, acetone-d6, DMSO-d6, CD3CN, AcOD, and MeOD. The influences of the referencing method on the 77Se shifts using external or internal Me2Se or Ph2Se2 and solvent can add up to ΔδSe = ca. 80 ppm. In addition, we observed a temperature dependence of both the selenoureas and the reference reagent Ph2Se2 as well as a 77Se shift difference of the analyte caused by interaction with internally added Ph2Se2. The negative charge of deprotonated selenoureas shifts the values by an additional -20 ppm.

Hemilabile Thio– and Selenoethers in Bis(benzimidazolyl)Amine Copper Complexes Relevant to the Active Sites of Copper‐Dependent Monooxygenases

AbstractCopper complexes supported by benzimidazole‐based tetradentate neutral ligands featuring thio‐ and selenoether donors, resemble the coordination environment of the active site in copper dependent monooxygenases Dopamine‐β‐monooxygenase (DβM) and peptidylglycine‐α‐hydroxylating monooxygenase (PHM). The cuprous complexes react with O2 at low temperature generating a reactive copper‐oxygen species assigned to a side‐on cupric–superoxo complex, which activates the C─H bond of dihydroanthracene. Based on structural, 1H and 77Se NMR, and EPR spectroscopic characterization, together with DFT computations, the selenoether moiety likely acts as a hemilabile ligand in these scaffolds, which results in an electrophilic cupric–superoxide intermediate poised for H‐atom transfer, as has been proposed for related bis(benzimidazole)‐thioether analogues and selenoether‐modified enzymatic systems.

3D Lead-Organoselenide-Halide Perovskites and their Mixed-Chalcogenide and Mixed-Halide Alloys.

We incorporate Se into the 3D halide perovskite framework using the zwitterionic ligand: SeCYS (+NH3(CH2)2Se-), which occupies both the X- and A+ sites in the prototypical ABX3 perovskite. The new organoselenide-halide perovskites: (SeCYS)PbX2 (X=Cl, Br) expand upon the recently discovered organosulfide-halide perovskites. Single-crystal X-ray diffraction and pair distribution function analysis reveal the average structures of the organoselenide-halide perovskites, whereas the local lead coordination environments and their distributions were probed through solid-state 77Se and 207Pb NMR, complemented by theoretical simulations. Density functional theory calculations illustrate that the band structures of (SeCYS)PbX2 largely resemble those of their S analogs, with similar band dispersion patterns, yet with a considerable band gap decrease. Optical absorbance measurements indeed show band gaps of 2.07 and 1.86 eV for (SeCYS)PbX2 with X=Cl and Br, respectively. We further demonstrate routes to alloying the halides (Cl, Br) and chalcogenides (S, Se) continuously tuning the band gap from 1.86 to 2.31 eV-straddling the ideal range for tandem solar cells or visible-light photocatalysis. The comprehensive description of the average and local structures, and how they can fine-tune the band gap and potential trap states, respectively, establishes the foundation for understanding this new perovskite family, which combines solid-state and organo-main-group chemistry.

3D Lead‐Organoselenide‐Halide Perovskites and their Mixed‐Chalcogenide and Mixed‐Halide Alloys

AbstractWe incorporate Se into the 3D halide perovskite framework using the zwitterionic ligand: SeCYS (+NH3(CH2)2Se−), which occupies both the X− and A+ sites in the prototypical ABX3 perovskite. The new organoselenide‐halide perovskites: (SeCYS)PbX2 (X=Cl, Br) expand upon the recently discovered organosulfide‐halide perovskites. Single‐crystal X‐ray diffraction and pair distribution function analysis reveal the average structures of the organoselenide‐halide perovskites, whereas the local lead coordination environments and their distributions were probed through solid‐state 77Se and 207Pb NMR, complemented by theoretical simulations. Density functional theory calculations illustrate that the band structures of (SeCYS)PbX2 largely resemble those of their S analogs, with similar band dispersion patterns, yet with a considerable band gap decrease. Optical absorbance measurements indeed show band gaps of 2.07 and 1.86 eV for (SeCYS)PbX2 with X=Cl and Br, respectively. We further demonstrate routes to alloying the halides (Cl, Br) and chalcogenides (S, Se) continuously tuning the band gap from 1.86 to 2.31 eV–straddling the ideal range for tandem solar cells or visible‐light photocatalysis. The comprehensive description of the average and local structures, and how they can fine‐tune the band gap and potential trap states, respectively, establishes the foundation for understanding this new perovskite family, which combines solid‐state and organo‐main‐group chemistry.

Mesoionic Janus-Type Dicarbene: Complexes, Adducts, and Catalytic Studies.

The preparations of homo- and hetero-bimetallic complexes as well as thiourea and selenourea derivatives of a mesoionic Janus-type N-heterocyclic dicarbene (diNHC) are reported. Analogues of its monocationic intermediate NHC have also been obtained for comparison. Using the main group adducts, the π-acceptor properties of both NHCs were determined using low temperature 77Se NMR spectroscopy completing their stereoelectronic profiling. Moreover, catalytic investigations reveal that the mesoionic dipalladium Janus-diNHC complex can be used in the sequential C2- and C5-arylation of 1-methylpyrrole for the preparation of non-symmetrical 2,5-diarylpyrroles.

Precision detection of cyanide, fluoride, and hydroxide ions using a new tetraseleno-BODIPY fluorescent sensor

A new chemosensor based on Seleno-BODIPY (4) was designed and synthesized for the rapid and sensitive detection of CN–, F−, and OH– ions in THF, exhibiting ultra-low detection limits of 26.26 nM, 43.05 nM, and 8.64 nM, respectively, through a turn-on fluorescent process. The seleno-funcionalization step was based on a novel methodology developed by our group, allowing direct functionalization of the BODIPY core. This procedure involves a quick reaction utilizing Ph2Se2 as a selenium source, BPO (benzoyl peroxide), and p-TSA (p-toluenesulfonic acid) in acetonitrile, enabling the production of the corresponding chalcogenated BODIPYs containing one to four selenium groups, demonstrating its versatility. The structure of BODIPY 4 was confirmed by HRMS, 1H, 13C, 77Se NMR, and IR spectra, and its photophysical properties were also evaluated. BODIPY 4 was applied to detect CN–, F−, and OH– ions in dual-mode detection (UV–Vis and fluorescence spectra), displaying a ratiometric response. The new probe exhibited a fast response time, visual color change from blue to fluorescent yellow, and high sensitivity and selectivity for these analytes over other selected anions. Mechanistic investigation through mass analysis revealed that the detection of these anions by BODIPY 4 occurs via an Aromatic Nucleophilic Substitution reaction with phenylselenide as the leaving group.

The Effect of Selenium-Based Ligands on Tungsten Acetylene Complexes.

Bioinspired tungsten acetylene complexes containing pyridine-2-selenolato (PySe) or 6-methyl-pyridine-2-selenolato (6-MePySe) ligands were synthesized. 77Se NMR spectroscopy allowed for an assessment of the resonance structures in the pyridine-2-selenolato ligands and the rationalization of chemoselectivity observed in regard to 1,2 migratory insertion of HC≡CH. [W(CO)(C2H2)(CHCH-PySe)(PySe)] is formed exclusively via insertion of HC≡CH into the W-N bond, while the use of bulkier 6-MePySe allows for the isolation of [W(CO)(C2H2)(6-MePySe)2], which only partially reacts with excess HC≡CH to give [W(CO)(C2H2)(CHCH-6-MePySe)(6-MePySe)]. Oxidation of [W(CO)(C2H2)(6-MePySe)2] with pyridine-N-oxide gave the tungsten(IV) complex [WO(C2H2)(6-MePySe)2]. Complexes [W(CO)(C2H2)(6-MePySe)2] and [WO(C2H2)(6-MePySe)2] react with trimethyl phosphine to carbyne complex [W(CO)(CCH2PMe3)(PMe3)2(6-MePySe)]Cl and alkylidene complex [WO(CHCHPMe3)(PMe3)2(6-MePySe)]Cl, respectively. The addition of substituted alkynes to [W(CO)3(PySe)2] via thermal decarbonylation gave complexes [W(CO)(MeC≡CMe)(PySe)2] and [W(CO)(HC≡Ct-Bu)(PySe)2], respectively. The here presented complexes are relevant for the modeling of the active site of acetylene hydratase from Pelobacter acetylenicus, in which a tungsten atom is enclosed in a sulfur-rich coordination sphere. A recently published theoretical study concluded that the exchange of sulfur for selenium would increase the activity of the enzyme. Our findings contrast this claim as comparative analysis concludes negligible structural and electronic differences between the selenium-based and previously published sulfur-based complexes.

Synthesis and characterization of organoselenium based BODIPY and its application in living cells

Phenylselenide based BODIPY probe was successfully synthesized and characterized by NMR spectroscopic techniques (1H, 13C and 77Se NMR), mass spectrometry and single crystal XRD. Surprisingly, crystal packing diagram of the probe showed formation of 1-D strip through intermolecular F---H interaction. The probe was screened with various Reactive Oxygen Species (ROS) and found to be selective for superoxide ion over other ROS via “turn-on” fluorescence response. The probe selectively and sensitively detects superoxide with a lower detection limit (43.34 nM) without interfering with other ROS. The quantum yield of the probe was found to increase from 0.091 % to 30.4 % (334-fold) after oxidation. Theoretical calculations (DFT and TD-DFT) were also performed to understand the sensing mechanism of the probe. The probe was able to effectively detect superoxide inside living cells without any toxic effect.

Five Hypotheses on the Origins of Temperature Dependence of 77Se NMR Shifts in Diselenides.

Notable thermal shifts in diselenides have been documented in 77Se NMR for more than 50 years, but no satisfactory explanation has been found. Here, five hypotheses are considered as possible explanations for the large temperature dependence of the 77Se chemical shifts of diaryl and dialkyl diselenides compared to monoselenides and selenols. Density functional theory calculations are provided to bolster hypotheses and better understand the effects of barrier height and dipole energies. It is proposed that the temperature dependence of diselenide 77Se NMR chemical shifts is due to rotation around the Se-Se bond and sampling of twisted conformers at higher temperatures. The molecular twisting is solvent dependent; here, DMSO-d6 and toluene-d8 were evaluated. No correlation was established between para-substituents on diaryl diselenides and the magnitude of the change in the 77Se NMR shift (Δδ) with temperature.

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide.

This article describes the detailed analysis of the reaction between arylamines, such as aniline, o-anisidine, and methyl anthranilate, with selenium dioxide in acetonitrile. A systematic analysis of the reaction products with the help of 77Se NMR and single-crystal X-ray crystallography revealed that the reaction progress follows three major reaction pathways, electrophilic selenation, oxidative polymerization, and solvent oxidation. For aniline and o-anisidine, predominant oxidative polymerization occurred, leading to the formation of the respective polyaniline polymers as major products. For methyl anthranilate, the oxidative polymerization was suppressed due to the delocalization of amine lone pair electrons over the adjacent carboxylate function, which prompted the selenation pathway, leading to the formation of two of the isomeric diorganyl selenides of methyl anthranilate. The diaryl selenides were structurally characterized using single-crystal X-ray diffraction. Density functional theory calculations suggest that the highest occupied molecular orbital of methyl anthranilate was deeply buried, which suppressed the oxidative polymerization pathway. Due to solvent oxidation, oxamide formation was also noticed to a considerable extent. This study provides that utmost care must be exercised while using SeO2 as an electrophile source in aromatic electrophilic substitution reactions.

Synthesis, evaluation, and computational chemistry of novel selenenyl sulfides as 3C protease inhibitors with strong cell-based antiviral activity

The 3C protease (3Cpro) is an important enzyme for developing therapeutic medicines against some severe viral infections. In order to discover new classes of antiviral agents, 42 novel selenenyl sulfides were prepared and characterized by 1H NMR, 13C NMR, 77Se NMR and HRMS. The target compounds demonstrated promising inhibitions against 3Cpro from either enterovirus 71 (EV71) or coxsackievirus B3 (CVB3), as well as desirable cell-based antiviral activity against these viruses. Among them, 11f displayed the most potent IC50 value of 0.28 ± 0.05 μM against EV71-3Cpro, and the strongest IC50 value of 0.72 ± 0.15 μM against CVB3, with a selectivity index of 51.5 against Hela cell, superior to the control drug rupintrivir. In addition, molecular docking was undertaken to predict a possible binding mode for compound 11f, and a comparative molecular field analysis (CoMFA) model was subsequently generated to understand the structure-activity relationships. Overall, the present research has provided some new insights to design a distinct family of antiviral compounds.