1H NMR Research Articles

Identification and characterization of Morganella morganii strain YC12-C3 and Enterococcus faecalis strain YC12-C10 and elucidation of its deoxynivalenol-degrading potential.

Deoxynivalenol ( DON) is one of the most harmful mycotoxins in food or feed or Traditional Chinese Medicine. An efficient and applicable method for the detoxification of DON is urgently developed. 1152 strains were isolated from the intestinal contents of crucian. Morganella morganii YC12-C3 and Enterococcus faecalis YC12-C10 were screened with the highest degradation rate of DON via HPLC methods. The optimal degradation condition of YC12-C3 and YC12-C10 is co-cultured 24 h and 36 h at 28 ℃ in LB medium with pH 7 and 1.0% inoculation dosage, respectively. LC-MS/MS and 1H NMR results show that YC12-C10 and YC12-C3 can transform DON to 3-deoxy-6-demethanol-DON, a new metabolite biotransformed from DON, by deoxidization at C3 hydroxy and de-methanal reaction at methanol moiety of C6. In addition, the DON-degradation in agricultural material assay showed that YC12-C10 and YC12-C3 can degrade 150 μg·kg-1 DON in Coix lacryma-jobi, with a degradation rate of 68.89% and 59.94%, respectively. This result shows that YC12-C10 and YC12-C3 have a sound efficiency in removing DON ability in Coix lacryma-jobi, providing a new strain resource and application technique for biological detoxification of DON in food or feed or TCM industry.

Crystal structures and photophysical properties of mono- and dinuclear ZnII complexes flanked by triethylammonium

Two new zinc(II) complexes, triethylammonium dichlorido[2-(4-nitrophenyl)-4-phenylquinolin-8-olato]zinc(II), (C6H16N){Zn(C21H13N2O3)Cl2] (ZnOQ), and bis(triethylammonium) {2,2′-[1,4-phenylenebis(nitrilomethylidyne)]diphenolato}bis[dichloridozinc(II)], (C6H16N)2[Zn2(C20H14N2O2)Cl4] (ZnBS), were synthesized and their structures were determined using ESI–MS spectrometry, 1H NMR spectroscopy, and single-crystal X-ray diffraction. The results showed that the ligands 2-(4-nitrophenyl)-4-phenylquinolin-8-ol (HOQ) and N,N′-bis(2-hydroxybenzylidene)benzene-1,4-diamine (H2BS) were deprotonated by triethyl-amine, forming the counter-ion Et3NH+, which interacts via an N—H...O hydrogen bond with the ligand. The ZnII atoms have a distorted trigonal–pyramidal (ZnOQ) and distorted tetrahedral (ZnBS) geometries with a coordination number of four, coordinating with the ligands via N and O atoms. The N atoms coordinating with ZnII correspond to the heterocyclic nitrogen for the HOQ ligand, while for the H2BS ligand, it is the nitrogen of the imine (CH=N). The crystal packing of ZnOQ is characterized by C—H...π interactions, while that of ZnBS by C—H...Cl interactions. The emission spectra showed that ZnBS complex exhibits green fluorescence in the solid state with a small band-gap energy, and the ZnOQ complex does exhibit non-fluorescence.

Synthesis of Tryptamine-Thiazolidin-4-one Derivatives and the Combined In Silico and In Vitro Evaluation of their Biological Activity and Cytotoxicity.

Tryptamine, a monoamine alkaloid with an indole ring structure, is derived from the decarboxylation of the amino acid tryptophan, which is present in fungi, plants, and animals. Tryptamine analogues hold significant therapeutic potential due to their broad pharmacological activities, including roles as neurotransmitters and potential therapeutic agents for various diseases. Structural modifications of tryptamine enhance receptor selectivity and metabolic stability, improving therapeutic efficacy. These modifications are crucial for optimizing pharmacokinetic and pharmacodynamic properties, making the analogues more effective and safer for clinical use. In this study, novel tryptamine-thiazolidin-4-one (YS1-12) derivatives were synthesized via a one-pot three-component condensation reaction. The synthesized compounds are characterized by different spectroscopy techniques such as FT-IR, 1H NMR, 13C NMR, and HR-NMS. The synthesized compounds were subjected to binary QSAR disease models for bioactivity prediction and a target prediction model for target analysis. Potential targets were identified, and physics-based molecular simulations were conducted. Additionally, MM/GBSA binding free energy analysis was performed to calculate the average binding free energies of YS1-12 compared to reference molecules. Our computational results indicated promising biological activities for these new compounds. To further investigate these activities, the compounds were tested in vitro using two different cancer cell lines: YKG-1 glioblastoma and SH-SY5Y neuroblastoma cells. The results confirmed the potential activities of these novel compounds. Notably, compounds YS4 and YS10 exhibited favorable activities compared to the control compounds 5-FU and Temozolomide. YS4 demonstrated an IC50 value of 20 nM against YKG-1 cells, while YS10 exhibited an IC50 value of 0.44 nM against SH-SY5Y cells.

Synthesis of novel meta-diamide compounds containing pyrazole moiety and their insecticidal evaluation

Abstract A novel series of meta-diamide compounds incorporating a pyrazole moiety (2a–2v) were designed and synthesized based on cyproflanilide. Their structures were validated through 1H NMR, 13C NMR, and HRMS analyses. These compounds were evaluated for their insecticidal activity against Plutella xylostella, Mythimna separate, Tetranychus cinnabarinus, and Nilaparvata lugens. Most of the title compounds exhibited good activity against N. lugens at 400 mg/L. Compound 2k demonstrated potential for further optimization as an insecticidal lead, thereby extending the application of meta-diamide compounds in the field of sucking mouthparts.

A Double‐walled Noncovalent Carbon Nanotube by Columnar Packing of Nanotube Fragments

Herein, we report the synthesis of double‐walled noncovalent carbon nanotubes (CNTs) through host–guest complexation of nanotube fragments and tube‐forming crystal engineering. As the smallest fragment of double‐walled CNTs, a host–guest complex of perfluorocycloparaphenylene (PFCPP) and carbon nanobelt (CNB) was synthesized by mixing them in solvents. The immediate complexation of the PF[12]CPP⊃(6,6)CNB complex with a remarkably high association constant (Ka) of 2×105 L/mol was observed. Time‐dependent 1H NMR and thermogravimetry measurements revealed that the stability of (6,6)CNB was significantly improved by encapsulation. X‐ray crystallography confirmed the robust belt‐in‐ring structure of this complex. As indicated by the short distance between PF[12]CPP and (6,6)CNB (2.8 Å), intermolecular orbital interactions exist between the belt and the ring, which were further supported by theoretical calculation and phosphorescence quenching experiments. While the PF[12]CPP⊃(6,6)CNB complex adopts various crystal packing structures, chloroform was discovered to be a magic “glue” solvent inducing one‐dimensional alignment of the PF[12]CPP⊃(6,6)CNB complex to build an unprecedented double‐walled noncovalent CNT structure.

Conformational Plasticity Enhances the Brain Penetration of a Metabolically Stable, Dual-Functional Opioid-Peptide CycloAnt.

CycloAnt is an opioid peptide that produces potent and efficacious antinociception with significantly reduced side effects upon systemic administration in mice. To verify its CNS-mediated antinociception, we determined its binding affinity at the opioid receptors, its proteolytic stability in mouse serum, metabolic stability in mouse liver microsomes, and pharmacokinetics in mice. CycloAnt exhibited stability toward proteolytic degradation in serum and resistance against metabolism mediated by cytochrome P450 enzymes (CYP450s) and UDP-glucuronosyl transferases (UGTs) in mouse liver microsomes. A pharmacokinetic study of CycloAnt in mice confirmed that CycloAnt crossed the blood-brain barrier (BBB) with a brain-to-plasma ratio of 11.5%, a high extent of BBB transport for a peptide. To elucidate the structural basis underlying its BBB penetration, we investigated its conformation in water and DMSO using 1H NMR spectroscopy. The results show that CycloAnt displays an extended conformation in water with most amide NHs being exposed, while in less polar DMSO, it adopts a compact conformation with all amide NHs locked in intramolecular hydrogen bonds. The chameleonic property helps CycloAnt permeate the BBB.

Monomer extraction from polymers using supercritical CO2

Polymerization reactions often leave unreacted monomers in the polymer. These unreacted monomers can emit vapors at ambient temperatures that cause unpleasant odors, pose both environmental and safety risks, and negatively impacts polymer properties. Therefore, a purification step is necessary after polymerization to remove these residual monomers. High temperature devolatilization is the currently applied technique of removing these monomers, however this treatment can also negatively impact the properties of the polymer. In this study the possibility of using supercritical CO2 (scCO2) as an extraction medium of these residual monomers, which are considered as Volatile Organic Compounds (VOCs), has been investigated experimentally. Polymer samples of either PS or PMMA with 4–7 wt% of residual monomers were extracted continuously with scCO2 at temperatures ranging from 50 to 90 °C and pressures of 100–400 bar. The measured extraction efficiencies, based on 1H NMR analysis, were 99+% and was reached between 4 and 16 h depending on the experimental conditions. In general, higher temperatures and higher pressures lead to enhanced extraction rates and thus higher efficiencies at shorter process times. The experimental results were successfully modelled with an empirical extraction simulation model as originally proposed by Sovová.

A Double-walled Noncovalent Carbon Nanotube by Columnar Packing of Nanotube Fragments.

Herein, we report the synthesis of double-walled noncovalent carbon nanotubes (CNTs) through host-guest complexation of nanotube fragments and tube-forming crystal engineering. As the smallest fragment of double-walled CNTs, a host-guest complex of perfluorocycloparaphenylene (PFCPP) and carbon nanobelt (CNB) was synthesized by mixing them in solvents. The immediate complexation of the PF[12]CPP⊃(6,6)CNB complex with a remarkably high association constant (Ka) of 2×105 L/mol was observed. Time-dependent 1H NMR and thermogravimetry measurements revealed that the stability of (6,6)CNB was significantly improved by encapsulation. X-ray crystallography confirmed the robust belt-in-ring structure of this complex. As indicated by the short distance between PF[12]CPP and (6,6)CNB (2.8 Å), intermolecular orbital interactions exist between the belt and the ring, which were further supported by theoretical calculation and phosphorescence quenching experiments. While the PF[12]CPP⊃(6,6)CNB complex adopts various crystal packing structures, chloroform was discovered to be a magic "glue" solvent inducing one-dimensional alignment of the PF[12]CPP⊃(6,6)CNB complex to build an unprecedented double-walled noncovalent CNT structure.

Effects of three elicitors on primary metabolism six days after treatment in healthy <i>Vitis vinifera</i> leaves and eight days after treatment in healthy and downy mildew-inoculated leaves

Elicitors can be used to reduce the application of conventional pesticides against grapevine diseases; however, they may disrupt plant primary metabolism. The long-term effects (more than 6 days after treatment) of applying plant defence stimulators (PDS) to protect grapevine from Plasmopara viticola were investigated. We studied the effect of three PDS (acibenzolar-S-methyl/ASM, potassium phosphonate/PHOS, methyl jasmonate/MeJA) and one surfactant (Triton) on gene expression and metabolite production in leaves of Vitis vinifera cv. Cabernet-Sauvignon before or after their inoculation with P. viticola. The molecular and biochemical results show the impact of these PDS on grapevine metabolism more than 6 days after treatment, and after inoculation. High-throughput q-RT-PCR revealed that sixty of the primary metabolism genes (ion homeostasis and hormones pathways) were modulated by all treatments, some modulations being specific to a given PDS. Meanwhile, 1H NMR studies revealed variations in metabolite abundances (amines, amino acids, organic acids, polyphenols and sugars), with some being common to all treatments (organic acid increase) and others specific to a single one. By combining two methodological approaches, it was possible to determine the specific effects of each PDS on Vitis. All PDS-induced resistance involved modulation of the primary metabolism. This innovative approach can be extended to vineyard studies in order to help better understand the variability of PDS effects in natura.

Rapidly Screening the Correlation between the Rotational Mobility and the Hydrogen Bonding Strength of Confined Water.

Automated Deuterium Relaxation-Ordered SpectroscopY in solution (ADROSYS), an automated two-dimensional deuterium NMR methodology, discriminates between D2O populations (as well as deuterium-labeled alcohol groups) whose properties differ as a result of being confined inside nanoscale volumes. In this contribution, a proof-of-principle demonstration on reverse micelles (RMs) yields the insight that as the length scale of the confinement decreases from several nanometers down to less than a nanometer, the position of the signal peak migrates through the two-dimensional (2D) spectrum, tracing out a distinctive path in the 2D space (of relaxation time vs chemical shift). The signals typically follow a relatively gentle linear path for water confined on the scale of several nanometers, before curving once the surfactants confine the water molecules to length scales smaller than 1-2 nm. The qualitative shape of this path, especially in the regime of strong confinement, can change with different choices of surfactants, i.e., a different choice of chemistry at the edges of the confining environment. An important facet of this research was to demonstrate the relatively wide applicability of these techniques by showing that both: (1) Standard modern NMR instrumentation is capable of deploying an automated measurement, even though the choice of a deuterium nucleus is nonstandard and frequently requires companion proton spectra in order to reference the chemical shifts; and (2) well-established (though underutilized) modern techniques can process the resulting signal even though it involves the somewhat unusual combination of chemical shifts along one dimension and a distribution of relaxation times along another dimension. In addition to demonstrating that this technique can be deployed across many samples of interest, detailed facts pertaining to the broadening or shifting of resulting signals upon inclusion of various guest molecules are also discussed.

Thiazolidine-4-one Analogues: Synthesis, In-Silico Molecular Modeling, and In-vivo Estimation for Anticonvulsant Potential.

Epilepsy is a critically deep-rooted CNS disorder affecting above 50 million people all over the world. Thus, a safe and effective treatment that proves its worth in this ailment is urgently needed. Thiazolidine-4-ones possess the molecules to be used as anticonvulsants. The thiazolidinedione is a cyclic analogue of thiosemicarbazides and thioureas as well as a (bio)isostere of hydantoin (imidazolidine-2,4-dione), which are recognized as novel anticonvulsant designs. This study aimed to develop and evaluate a novel thiazolidine-4-one derivative by three-component condensation in one pot reaction method. A novel thiazolidine-4-one derivative was formulated by three-component condensation. The selected OH (Alcohol) derivatives were found to be more potent; hence, a molecular docking study against a selected target LGI1 LRR domain was performed. Various analytical tests like FTIR and H1 NMR were accomplished. The FTIR was used to validate the existence of multiple functional moieties like C-S, O-H, C=O, C-N, N=O, C-NH, C-O in the wave region from 3075 cm-1 - 1236 cm-1 and H1 NMR was employed to ascertain if the synthesized analogues had the complete set of protons. Then, the anti-seizure activity of the selected compound was examined using PTZ models in mice at three successive doses, i.e., 25, 50, and 100mg/kg, and compared with standard ethosuximide. The docking simulations were initiated using PyMOL after the binding site was determined and the receptor and ligand were suitably prepared. It showed higher binding frequency in comparison to the standard marketed drug Ethosuximide. FTIR and H1 NMR spectroscopy were used to characterize the chemical components. Numerous functional groups, including O-H (alcohol), C=O (ketones), N=O, C-NH, C-N, C-S, and C-O bending stretching, were visible in the synthesized molecule accordingly. The synthesized compound was effective in inhibiting the convulsions at the concentration of 100 mg/kg. The novel thiazolidine-4-one derivative showed promising activity and could be considered for further investigation and dosage form preparation.

The First N,O-Chelated Diphenylboron-Based Fluorescent Probe for Peroxynitrite and Its Bioimaging Applications

Peroxynitrite (ONOO−) is a reactive oxygen species (ROS) that takes part in the oxidation-reduction homeostasis while at the same time being responsible for activating numerous pathological pathways. Accordingly, monitoring the dynamic changes in ONOO− concentration has attracted a great deal of attention, undoubtedly prompting the development of appropriate fluorescent chemosensors. Herein, we developed a novel N,O-chelated diphenylboron-based fluorescent probe (DPB) for ONOO− featuring high selectivity, a quick response time (2.0 min), and a low detection limit (55 nM). DPB incorporates tetra-coordinated boron in the center of the fluorogenic core and a three-coordinated boron from the pinacolphenylboronate fragment, which acts as the recognition site for ONOO−. As confirmed by HR-MS and 1H NMR, the interaction of DPB with ONOO− led to an oxidative cleavage of pinacolphenylboronate moiety to produce strongly emissive derivative DPB-OH. The fluorescence enhancement is likely a result of a substantial deactivation of non-radiative decay due to the replacement of the bulky pinacolphenylboronate moiety with a compact hydroxyl group. Importantly, DPB probe exhibits negligible cytotoxicity and favorable biocompatibility allowing for an efficient tracking of ONOO− in living cells and zebrafish. Overall, the current study does not only represents the first N,O-chelated diphenylboron-based fluorescent probe for a specific analyte, but also serves as a guideline for designing more potent fluorescent probes based on the chemistry of boron chelates.

Physicochemical and biological evaluation of ‘click’ synthesized vinyl epoxide-chitosan film for active food packaging

Chitosan (Cs) being a natural biopolymer serves as an excellent template to construct active packaging materials for achieving sustainable development. In this study, Cs was chemically modified via epoxide ring opening click reaction using vinyl epoxide to obtain a novel chitosan vinyl epoxide (Cs-VE) derivative with hydroxyl and olefinic functional groups. The Cs-VE transparent film was fabricated through the eco-friendly solution casting technique. A meticulous investigation into the chemical structure and physicochemical properties of the synthesized films was conducted using FT-IR, 1H NMR and XRD analyses. The thermal stability and homogeneity of the film were verified by thermogram and FE-SEM images respectively. Improved mechanical properties (tensile strength of 24.64 MPa and 12.08 % elongation at break) and excellent UV-light blocking ability (9.3 % transmittance at 350 nm and 22.15 % transparency at 600 nm) were observed. Also, important parameters such as water vapor permeability (WVP), swelling degree, water solubility and UV-barrier properties were found to be adequate for food packaging application. Similarly, enhanced antioxidant activity with 27.2 % and 73.6 % radical scavenging against DPPH and ABTS radicals respectively was observed for the synthesized Cs-VE film. The film showed antimicrobial activity against both bacteria and fungi. These results along with food packaging studies on Grewia asiatica fruit established the developed Cs-VE film as a suitable candidate for active food packaging application.

Analysis of Water Adsorption Capacity, Thermal Behavior, Antioxidant Activity, and Smoke Volume by Polyol Ester in Reconstituted Tobacco.

A series of ester derivatives with hydroxyl groups were created by esterification of 1,2-propanediol and glycerol with o-toluoyl chloride via the catalyst 4-dimethylaminopyridine (DMAP). All the compounds were verified using nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy, and high resolution mass spectrometry. Moisture absorption and desorption experiments were carried out on the compounds' pure systems and their systems in reconstituted tobacco, while their hygroscopicity and moisturizing properties were evaluated using low-field nuclear magnetic resonance imaging. Two compounds with better absorption and moisture retention were selected: 4 (1-hydroxypropan-2-yl 2-methylbenzoate) and 6 (2,3-dihydroxypropyl 2-methylbenzoate), respectively. Moreover, the thermal stability of compounds 4 and 6 were investigated using thermogravimetric (TG) analysis. The results of TG-DTG showed that the maximum mass loss rate of compound 4 appeared at 251.67 °C, with a mass loss rate of 87.61%. At the peak temperature of 291.83 °C, 6 showed the highest decomposition rate with 49.23% mass loss rate. To explore the antioxidant properties, we constructed three different antioxidant systems. Furthermore, compound 6 showed excellent effects, with scavenging rates reaching 69.28%, 71.92%, and 75.93%, respectively. Smoke volume results indicated that the compounds optimally replaced propanediol and glycerol at a rate of 40%. The results provide a theoretical reference for the development of new moisturizing agents based on polyol esters in the tobacco industry.

Synthesis and self-assembly of perylene-cored poly(amidoamine) dendrimers with poly[2-(dimethylamino)ethyl methacrylate]-modified arms as fluorescent bio-imaging probes and doxorubicin carriers

A poly(amidoamine) (PAMAM) dendrimer is prepared using a divergent method, with perylene-3,4,9,10-tetracarboxylic diimide (PTCDI) as luminescent core. The peripheral amines are modified using α-bromoisobutyryl bromide, allowing the dendrimers to act as macroinitiators for the synthesis of poly[2-(dimethylamino)ethyl methacrylate] (PDMAEMA) through atom transfer radical polymerization (ATRP) with three different degrees of polymerization. The successful synthesis is verified by conducting a range of analyses, including Fourier-transform infrared (FT-IR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy, and X-ray diffraction (XRD). Additionally, the impact of changes in solution pH on the self-assembly of dendrimers is explored. Field emission scanning electron microscopy (FE-SEM) and dynamic light scattering (DLS) showed unique morphologies, including spherical micelles and cubic-hexagonal structures, at varying pH levels. The self-assembled dendrimers are utilized to load doxorubicin (DOX) and the drug release kinetics are studied under various conditions. The biocompatibility of the dendrimers is assessed using the MTT assay against SH-SY5Y cells. Additionally, higher dendrimer generations improved the solubility, compatibility, and fluorescent properties of the core. The dendrimers' capacity for cellular uptake and fluorescence imaging is also evaluated using SH-SY5Y cells, demonstrating their effectiveness in live-cell fluorescence imaging.

Dibenzoxanthene-β-lactam hybrids as potential antioxidant and anticancer agents: Synthesis, biological evaluation, and docking study

In this study, we designed and synthesized a series of β-lactam compounds bearing 14-phenyl-14H-dibenzo[a,j]xanthene moiety attached to the N-1 position of the β-lactam ring through a [2 + 2] cycloaddition process. All the synthesized compounds have been characterized by elemental analysis, Fourier-transform infrared (FT-IR) and nuclear magnetic resonance (1H NMR and 13C NMR) spectral analysis. These derivatives were evaluated for their anticancer and antioxidant activities. The in vitro anticancer activity of new compounds was examined against MCF-7 (breast cancer), HepG2 (liver hepatocellular carcinoma), and TC-1 (mouse lung epithelial) cell lines by 3-(4, 5-dimethylthiazolyl-2)-2, 5-diphenyltetrazolium bromide (MTT) assay. Notably, compounds 4c, 4e and 4 g demonstrated significant anticancer activity against TC-1 cell line. Additionally, compounds 4c, 4f and 4 g exhibited promising levels of efficacy against the MCF-7 cell line. The diphenylpicrylhydrazyl (DPPH) radical scavenging assay indicated that 4h and 4i are more potent antioxidant agents than the Vitamin C, while 4a, 4b, 4c, and 4j exhibited moderate antioxidant capabilities. Furthermore, the docking simulations are consistent with the biological assay results, indicating that the hybrids may bind to protein targets through hydrogen bonding and other nonvalent interactions.

Passivator materials based on the benzothiazole-sulfonamide hybrid: Synthesis, optical, electrochemical properties, and molecular modeling for perovskite solar cells

This study presents the synthesis of N-(4-(N-carbamimidoylsulfamoyl)phenyl)benzo[d]thiazole-2-carbohydrazonoyl cyanide (NCSBC), a novel passivator material for perovskite solar cells (PSCs). The structure was confirmed by FTIR, ¹H NMR, and ¹³C NMR, while Hall-effect measurements revealed a hole mobility of 1.15 × 10³ cm²/Vs. UV–Vis analysis showed absorption peaks at 295 and 422 nm, corresponding to transitions related to azo groups and aromatic rings in NCSBC. The compound exhibited an optical energy gap of 2.47 eV, consistent with DFT-based molecular modeling. Thermal stability and electrochemical properties further validated its suitability for photovoltaic applications. Incorporating NCSBC into PSCs with an FTO/c-TiO2/MAPbI3/NCSBC/spiroMeOTAD/Ag device configuration resulted in a power conversion efficiency (PCE) of 16.21 %, compared to 14.47 % for the control. This work highlights NCSBC's potential for cost-effective, high-efficiency defect passivation in PSCs.

Synthesis and Anti-Inflammatory Activity of New Nicotinoyl Amides

The article presents the results of a study of the amination reaction of nicotinic acid chlorohydride with amines morpholine, cytisine, and 1-aminoadamantane, which are often used in the search and creation of drugs for respiratory and circulatory stimulants. The study was conducted to search for new biologically active compounds with anti-inflammatory activity. The synthesis of new aminoamides was carried out by the interaction of nicotinic acid with molecules of morpholine, cytisine, and adamantane in anhydrous ethanol. As a result of the conducted studies, new amides of nicotinic acid with high yields (90.7–93.1%) were obtained. The structures of the new compounds were determined using NMR 1H and 13C spectroscopy methods, as well as data from two-dimensional spectra of COSY (1H-1H), HMQC (1H-13C), HMBC (1H-13C) and mass spectrometry. The results of an experimental study of the anti-inflammatory activity of synthesized new amides are presented. The anti-inflammatory effect of nicotinic acid N-adamantylamide was established, other new amides were ineffective compared with ibuprofen (p2 < 0.05).

Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione

The reactions of lupinine alkaloid and its chlorine derivative with cinnamoyl chloride and 2-K-isoindole-1,3-dione were investigated to obtain 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester and 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione, respectively. The optimal conditions for carrying out the aforementioned reactions were determined, taking into account the nature of the solvent and medium. It was established that acylation of the molecule in a benzene medium, in the presence of trimethylamine, resulted in the formation of 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester, with an 82% yield. It was demonstrated that the interaction of chlorolupinine with 2-K-isoindole-1,3-dione under Gabriel reaction conditions resulted in the formation of 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione. The conformer with an axial orientation of the isoindole-1,3-dione substituent was observed to exhibit greater stability than the conformer with an equatorial orientation. The structure of the synthesized compounds was investigated by IR, 1H, and 13C NMR spectroscopy. The use of two-dimensional spectra in COSY (1H-1H) and HMQC (1H-13C) formats enabled the establishment of homo- and heteronuclear interactions, thereby confirming the structure of the compounds under investigation. The values of chemical shifts, multiplet and integrated intensity of 1H and 13C signals in one-dimensional NMR spectra of the novel compounds were determined. The crystal structures of 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester and 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione were elucidated through X-ray analysis.

Intermolecular Anionic Mixed‐Valence and π‐Dimer Complexes of ortho‐Pentannulated Bisazacoronene Diimide

AbstractThis study reports the serendipitous discovery of intermolecular anionic mixed‐valence (MV) and π‐dimer species in ortho‐pentannulated BisAzaCoroneneDiimides (BACDs) during their electrochemical reduction in a non‐aqueous solvent. A library of nitrogen‐containing extended PDIs was synthesized via an aza‐benzannulation reaction followed by a Pd‐catalysed ortho‐pentannulation reaction. Ortho‐pentannulated BACDs revealed strong aggregation abilities in solution. Concentration‐dependent UV/Vis absorption spectra, variable temperature 1H NMR experiments, and atomic force microscopy coupled to molecular dynamics support their self‐assembly into columnar aggregates. Cyclic voltammetry experiments in dichloromethane reveal prominent splitting of the first reduction wave, attributed to the formation of unprecedented intermolecular anionic MV and π‐dimers in organic solvent. These species were thoroughly characterized by real‐time spectroelectrochemistry, electrochemical simulations and theoretical calculations. Remarkably, this work underscores the tuneable nature of AzaBenzannulatedPerylene Diimides (AzaBPDIs) and BACDs, emphasizing their potential as a promising scaffold for designing supramolecular materials with long‐range radical anion delocalization. The observation of this phenomenon provides insights into the fundamental behaviour of supramolecular organic semiconductors, thereby paving the way for the development of novel electronic devices and electron‐deficient materials.