13C NMR Research Articles

Assessing [DMAP-DABCO]AcO as an effective dual basic ionic liquid for the synthesis of chromeno[2,3-d]pyrimidine derivatives and exploring their anti-cancer activity through computational analysis

Here, we report the synthesis of a new dual basic ionic liquid viz. 1-[3-(dimethylamino)propyl]-1,4-diazabicyclo[2.2.2]octan-1-ium acetate [DMAP-DABCO]AcO, and its use as a catalyst for the synthesis of chromeno[2,3-d]pyrimidine derivatives through multi-component reaction approach involving salicylaldehyde derivatives, secondary amines and malononitrile. The ionic liquid and the chromeno[2,3-d]pyrimidine derivatives were characterized using FT-IR, 1H and 13C NMR, and Mass spectrometry techniques. The synthesized derivatives were evaluated for their in vitro anti-cancer activity against the MCF7 cell line. The compound 4a showed the highest anti-cancer activity with an IC50 value of 65.25 µg/mL compared with the standard drug 5-FU. The anti-cancer activity of synthesized derivatives was additionally validated through computational studies, including molecular docking, density functional study (DFT), and absorption, distribution, metabolism, excretion, and (toxicity) ADME(T) analysis.

A novel pillar-layered MOF with urea linkers as a capable catalyst for synthesis of new 1,8-naphthyridines via the anomeric-based oxidation

Metal-based catalysts play an essential role in organic chemistry and the chemical industry. This research designed and successfully synthesized a pillar-layered metal–organic framework (MOF) with the urea linkers, namely Basu-HDI, as a novel and efficient heterogeneous catalyst. Various techniques such as FT-IR, EDX, elemental mapping, SEM, XRD, BET, and TGA/DTA studied its structure and morphology. Then, we investigated the synthesis of new 1,8-naphthyridines utilizing Basu-HDI in mild conditions via a one‐pot, three‐component tandem Knoevenagel/Michael/ cyclization/anomeric-based oxidation reaction. Final products were achieved by anomeric-based oxidation without employing an oxidation agent. Remarkably, this tandem process gave a good range of new 1,8-naphthyridines with high yields in a short reaction time. The pure products were confirmed by FT-IR, 1H NMR, 13C NMR, and mass spectrometry techniques. Moreover, the introduced catalyst showed good efficiency and stability and can be reused four times without significantly reducing efficiency.

Removal of Cr(VI) from aqueous phase using dimethylaminopropylamine anchored polystyrene‐co‐divinylbenzene polymer as adsorbent

AbstractThe current investigation delves into the effectiveness of dimethylaminopropylamine tethered onto polystyrene‐co‐divinylbenzene polymer for the proficient elimination of hexavalent chromium from simulated wastewater. The resin was characterized using SEM, FT‐IR spectroscopy, EDX, elemental analysis, thermogravimetry, and solid state 13C NMR spectroscopy. The experimental investigation into sorption dynamics involved varying process parameters, including initial Cr(VI) concentration, amount of adsorbent used, solution pH, temperature, and contact between phases. The binding modes of chromate ions, either bidentate or monodentate, were observed, with their manifestation influenced by the solution's pH. Sorption capacity was found to be pH‐dependent, with removal efficiencies of 98.27%, 96.38%, and 85.52% observed at pH levels of 3, 6, and 9, respectively. PS‐DMAPA resin demonstrated robust regeneration capabilities, throughout five consecutive adsorption–desorption cycles. The Langmuir adsorption model exhibited excellent agreement with the experimental findings (R2 = 0.9994), revealing a maximum adsorption capacity of 70.15 mg g−1 at 298 K. Additionally, the experimental findings closely matched the second‐order kinetic model. The kinetics of sorption and the thermodynamic parameters were also investigated. Performance evaluating of the PS‐DMAPA resin under dynamic conditions included analyzing the Cr(VI) breakthrough curve. The 10% sodium chloride solution was employed to effectively recover the extracted Cr(VI) quantitatively.

Synthesis and Anti-Inflammatory and Analgesic Potentials of Ethyl 2-(2,5-Dioxo-1-Phenylpyrrolidin-3-yl)-2-Methylpropanoate.

Background/Objectives: Inflammation and analgesia are two prominent symptoms and often lead to chronic medical conditions. To control inflammation and analgesia, many marketed drugs are in practice but the majority of them have severe side effects. Methods: This study involved the synthesis of a pivalate-based Michael product and evaluated it for in vitro COX-1, COX-2, and 5-LOX inhibitory potentials using specific assays. Molecular docking studies were also assessed. Based on the in vitro results, the compound was also subjected to in vivo anti-inflammatory and antinociceptive studies. Results: The pivalate-based Michael product (MAK01) was synthesized by an organocatalytic asymmetric Michael addition of ethyl isobutyrate to N-phenylmaleimide with an isolated yield of 96%. The structure of the compound was confirmed through 1H and 13C NMR analyses. The observed IC50 values for COX-1, COX-2, and 5-LOX were 314, 130, and 105 μg/mL, respectively. The molecular docking studies on the synthesized compound showed binding interactions with the minimized pockets of the respective enzymes. In a carrageenan model, a percent reduction in edema when administered at 10 mg/kg (a reduction of 33.3 ± 0.77% at the second hour), 20 mg/kg (a reduction of 34.7 ± 0.74% at the second hour), and 30 mg/kg (a reduction of 40.58% ± 0.84% after the fifth hour) was observed. The compound showed a significant response at concentrations of 50, 100, and 150 mg/kg with latency times of 10.32 ± 0.82, 12.16 ± 0.51, and 12.93 ± 0.45 s, respectively. Conclusion: In this study, we synthesized a pivalate-based Michael product for the first time. Moreover, based on its rationality and potency, it was found to be an effective future medicine for the management of analgesia and inflammation.

Enhancing CO2 uptake by aqueous K2CO3 solutions using H2O2‐derived reactive oxygen species: Novel rate promotion for CCU processes

AbstractThis study introduces a novel approach to promote CO2 absorption by aqueous K2CO3 solutions through the in‐situ generation of reactive oxygen species (ROS) via the alkali activation of H2O2. The superoxide radical anion (O2•‐) is recognized as a major contributor in this process, with its presence confirmed by UV‐Vis (Ultraviolet–visible) spectroscopy through the characteristic diformazan peak formed from the reaction between nitro blue tetrazolium (NBT) and superoxide. CO2 absorption experiments and 13C NMR (Carbon‐13 nuclear magnetic resonance) characterization demonstrate the enhanced efficiency of the promoted solution in both CO2 absorption and the conversion of K2CO3 to KHCO3. Comparative analysis with traditional promoters reveals the superior kinetic performance of the H2O2‐promoted system at room temperature. Notably, our system yields pure KHCO3 without by‐products, making it highly suitable for carbon capture and utilization (CCU) by enabling versatile subsequent transformation processes. © 2024 Society of Chemical Industry and John Wiley & Sons, Ltd.

Synthesis, characterization, proteolytic activity inhibition, ADMET prediction, and molecular docking studies of novel indole derivatives as potential SARS-CoV-2 protease inhibitors

Both the main protease (Mpro) and papain protease (PLpro) are fundamental enzymes in SARS-CoV-2 life cycle. In this study, we have targeted these two enzymes using novel indole derivatives as antiviral agents. The synthesized compounds were thoroughly characterized by Fourier-transform infrared spectroscopy (FT-IR), UV–vis, 1H, 13C, and 2D nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and melting point (m.p.). The optimized structure, reactivity, and stability of the synthesized compounds were calculated using Density Functional Theory (DFT) at the B3LYP/6–31G(d,p) level. Using in silico ADMET prediction along with molecular docking, we found that the synthesized compounds presented good docking scores and very low predicted inhibition constants (Pki) from low micromolar to nanomolar ranges. In particular, compounds 10 and 11 with respective Pki values of 1.68 μM and 387.71 nM for Mpro and 402.50 nM and 27.10 nM for PLpro. These two compounds are engaged in vast range of interactions with the active sites of both enzymes. Further in vitro investigations using fluorescence resonance energy transfer (FRET) assays demonstrated that compounds 10 and 11 inhibited Mpro proteolytic activity with approximate IC50 values of 20 µM and 10 µM, respectively. These findings suggest that these new indole derivatives could serve as promising candidates for the development of drugs against SARS-CoV-2 and potentially other future coronaviruses.

Linear‐ and Cyclo‐Hexa(amino)hexaboranes: New Routes to Synthesis of B6 Chain and B6 Ring

AbstractIn this work, a linear‐hexaborane(8) B6(NMe2)6(CH2SiMe3)2 was synthesized using a new method. By replacing one chlorine atom of Cl2B3(NMe2)3 with CH2SiMe3 group, compound ClB3(NMe2)3CH2SiMe3 was prepared. Reductive dehalogenative coupling of ClB3(NMe2)3CH2SiMe3 led to linear‐hexaborane(8). Moreover, the six‐membered boron ring, cyclo‐hexaborane B6(NEt2)6 was synthesized by reductive dehalogenation of Br2BNEt2. The first linear‐hexaborane(8) and cyclo‐hexaborane B6(NEt2)6 crystal structures were fully characterized by X‐ray structural analysis and 11B, 1H, and 13C NMR spectroscopy. While the B1⋅⋅⋅B6 chain in linear‐hexaborane(8) is strongly twisted at all B−B bonds, the B6 ring cyclo‐hexaborane B6(NEt2)6 has a chair conformation similar to cyclohexane.

Synergistic corrosion inhibition of mild steel by chalcone derivatives and KI in acidic media via computational and experimental methods

The corrosion inhibition characteristics of chalcone 4-hydroxy-6-methyl-3-(3-phenylacryloyl)-2H-pyran-2-one derivatives with different functional groups (H, Cl, -CH3, -NO2, -OCH3) studied employing density functional theory (DFT). The study identified the CH-OCH3 derivative as the most effective inhibitor among the compounds analysed. This derivative was synthesized and characterized through IR, 1H NMR and 13C NMR spectroscopy. The CH-OCH3 inhibitor then studied for its mild steel corrosion inhibition capability using Electrochemical and surface analysis in 1 M HCl. CH-OCH3 inhibitory efficacy rises in proportionately with their concentration, according to electrochemical results and reaches 85.4 % at 10−3 M. Potentiodynamic polarization revealed that it operates as mixed-kind of inhibiting nature. CH-OCH3 adheres to the Langmuir isotherm when they bind over the mild steel surface. The deposition of the inhibitors on metal surface is additionally verified by surface study utilizing AFM. Additionally, the influence of KI addition over CH-OCH3 inhibition property has been studied.

Water-Soluble Intracellular Polysaccharides (IPSW-2 to 4) from Phellinus igniarius Mycelia: Fractionation, Structural Elucidation, and Antioxidant Activity.

Phellinus igniarius is a medicinal fungus. Nonetheless, research on its water-soluble intracellular polysaccharides (IPSW-2 to 4) fractionation, structural elucidation, and antioxidant activity is limited. In this study, water-soluble intracellular polysaccharides (IPSW-2 to 4) were extracted and fractionated from P. igniarius mycelia, and their antioxidant and structural properties were assessed using GC-FID, GC-MS, FTIR, and NMR spectroscopy (1H and 13C). In the water-eluted P. igniarius polysaccharide fractions (IPS30W, IPS60W, and IPS80W) of anion-exchange chromatography, the polysaccharide content was 79.05%, 68.25%, and 62.06%, with higher yields of 25.07%, 21.38%, and 20.34%, respectively. In contrast, the salt (NaCl) elution fractions (IPS30S1, IPS60S1, IPS60S2, and IPS80S1) of anion-exchange chromatography had lower polysaccharide content and yield. Hence, water elution fractions (IPS30W, IPS60W, and IPS80W) were selected for further purification. After repeated purification using size-exclusion chromatography, IPSW-2 to 4 were obtained with a yield of 8% to 15.83%. The IPSW-2 to IPSW-4 structures were elucidated, and they showed no triple helical conformation. Based on periodate oxidation, Smith degradation, methylation analysis, and 1H and 13C NMR spectroscopy, the primary structures of IPSW-2, IPSW-3, and IPSW-4 were all glucan, with the main chain consisting of (1→6)-α-D-Glcp, (1→3,4)-α-D-Glcp, and (1→3, 6)-α-D-Glcp, with α-D-Glcp as a side chain. Finally, antioxidant analysis showed that IPS30W, IPS60W, and IPS80W were all more capable of scavenging superoxide anions than the polysaccharides of Phyllostachys (13.8%) and floribunda (15.1%) at the same concentration (0.40 mg/mL). This will serve as a guide for the development of functional foods.

Chemical Variability of the Leaf Essential Oil of Two Subspecies of Juniperus oxycedrus L. From Northwestern Algeria.

Thirty-seven essential oil samples have been isolated from leaves of individual plants of Juniperus oxycedrus (subspecies oxycedrus and macrocarpa) growing wild in Tlemcen and Aïn Témouchent provinces (Northwestern Algeria). Analysis of eight selected oil samples by GC(RI), GC/MS and 13C NMR, allowed the identification of 88 components that accounted for 84.4-99.5 % of the whole compositions. The 37 compositions were subjected to statistical analysis which suggested the existence of groups and sub-groups I, IIA and IIB. Group I, the most important group with 24 oil samples out of 37, differed from sub-groups IIA and IIB, essentially by the high content of α-pinene (mean value, 69.2 %; SD 6.24). Sub-groups IIA and IIB were differentiated by their content of α-pinene (Mean values, 49.7 % and 27.3 %, respectively) as well as δ-3-carene (10.3 %, sub-group IIA), sabinene and (Z)-6-pentadecen-2-one (8.7 % and 4.9 %, respectively, sub-group IIB).

Design, Synthesis of Flurbiprofen Based 1,3,4-Oxadiazoles and Constrained Anticancer, Antioxidant Agents: In silico Docking Analysis.

Flurbiprofen, a primary component of a nonsteroidal anti-inflammatory drug (NSAID) used to relieve symptoms of arthritis, and is a considerable interest in medicinal chemistry due to its demonstrated potential as an effective agent in various therapeutic applications. In consideration of the 1,3,4-oxadiazole therapeutic potential and anticancer activity, a new series of flurbiprofen scaffolds have been prepared through a straightforward reaction between 5-(1-(2-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazole-2-thiol (4) and various organic active 2-chloro-N-phenyl acetamides (5). The synthesized series (6a-6k) was characterized using a combination of spectroscopic techniques, including FT-IR, mass, 1H-NMR, and 13C NMR, followed by physical data. The cytotoxicity of the newly synthesized congeners was investigated against MCF-7 (human breast cancer cell line) and A-549 (human lung carcinoma epithelial) cell lines and anti-inflammatory activity as DPPH and H2O2 radical scavenging ability. In the series, analogues 6c, 6e, 6h, and 6k showed excellent inhibitory activity against MCF-7 cells in the range of IC50 values of 9.10-13.67 μg mL-1 compared to DXN (IC50=9.24 μg mL-1). In this series, analogues 6c, 6f, 6h, and 6j show remarkable H2O2 radical scavenging inhibition IC50 of 48.25±0.21, 47.33±0.15, 51.10±0.25, and 44.40±0.07 μM by using ascorbic acid as a standard, whose IC50 is 49.90±0.27 μM. According to the docking results, the most potent cytotoxic compounds have a stronger binding affinity with the Flurbiprofen complex (PDB: 1R9O) because of their interactions with residues such as Arg416(A), Trp103(A), Phe97(A), Gly279(A), Ile188(A), Glu283(A), Thr287(A), Val462(A), Phe459(A), Leu345(A), Ile417(A), and Cys418(A). Furthermore, in silico drug-likeness prediction analysis suggested that the majority of the synthesized compounds exhibit good oral bioavailability based on their Lipinski's Rule of Five and toxicity using ADME/Tox predictions.

Synthesis, spectral characterisation, DFT calculations, biological evaluation and molecular docking analysis of new Mannich compounds derived from cyclopentanone

This research outlines the efficient one-pot calcium chloride-catalysed synthesis of three novel Mannich bases: M1, M2 and M3. M1 and M2 resulted from the condensing of benzaldehyde with m-nitroaniline and m-bromoaniline, respectively, in conjunction with cyclopentanone. However, M3 was obtained through the reaction of p-methoxybenzaldehyde, m-bromoaniline and cyclopentanone. The isolated compounds were thoroughly characterised using elemental analysis and various analytical and spectroscopic techniques, including the determination of their melting points, electrospray mass spectrometry (ESMS), Fourier transform infrared (FTIR), electronic spectroscopy (UV–Vis), and nuclear magnetic resonance (NMR) spectroscopy (1H- and 13C NMR). Thermal stability (TGA and DTA analysis) of the three Mannich compounds was also examined. The newly synthesised Mannich bases exhibit remarkable potential as metal ion complexing agents and as fundamental building blocks for forming small organic molecules, particularly bioactive molecules and novel ligands for coordination chemistry. In addition to their structural significance, the biological efficacy of these compounds was assessed, revealing their excellent antimicrobial properties toward bacterial and fungal species. These activities suggest their potential use in combating microbial infections. Theoretical DFT simulations employing the B3LYP functional at the 6-311++G(d,p) level provided a thorough analysis of the stability of compounds, electrical properties, and geometry. Additionally, molecular docking studies of the Mannich compounds with two protein targets, 5IQ9 and 5VBU (both relevant for drug discovery) were performed. These studies revealed that the three Mannich compounds exhibit similar binding energies and effective interaction with both the 5IQ9 and 5VBU proteins, suggesting the potential of these Mannich compounds as dual inhibitors targeting both proteins.

PVA/AMPS hydrogels: Promising adsorbents for wastewater treatment with high efficiency and reusability

AbstractA PVAMPS hydrogel was synthesized through chemical cross‐linking and semi‐interpenetration of Poly (vinyl Alcohol) (PVA) and 2‐Acrylamido‐2‐methyl‐1‐propanesulfonic acid (AMPS) with glutaraldehyde in distilled water. Various ratios of PVA/AMPS, namely PVAMPS‐1 (2:1), PVAMPS‐2 (1:1), and PVAMPS‐3 (1:2), were examined to understand their individual impacts on gel formation. The synthesis of hydrogels was confirmed using FT‐IR and solid‐state 13C NMR spectroscopy. The PVAMPS hydrogels demonstrated high efficiency as a selective adsorbent for removing cationic dyes, such as Methylene Blue, Safranine‐O, and Thionine, from aqueous solutions, with over 90% removal of cationic dyes observed within 18 hours. Regeneration and reusability studies revealed that even after four cycles, the adsorption capacity of the PVAMPS hydrogels remained exceptionally high, with removal rates exceeding 90% for Methylene Blue. However, for Safranine‐O and Thionine, the removal rates dropped to 20% and 23%, respectively, after four cycles. These findings underscore the promising potential of PVAMPS hydrogels for the removal of cationic dyes in wastewater treatment.

Novel benzohydrazide derivative as a potential anticarcinogenic agent for breast cancer: Synthesis, crystal structure, in vitro and in silico assessments

Polycyclic aromatic compounds (PACs) are a class of organic molecules known for their significant biological activity, including anticancer properties. These compounds often interact with biological macromolecules, making them crucial in the development of new therapeutic agents. In this study, we report a new benzohydrazide derivative, (E)-4-(hexyloxy)-N'-(1-(naphthalen-2-yl)ethylidene)benzohydrazide (2), which incorporates a naphthalene ring, a typical PAC, as a core structural element. The structure of the compound was analyzed using FTIR, 1H NMR, 13C NMR and elemental analysis. Moreover, single crystal X-ray crystallography studies demonstrated that the compound adapted monoclinic crystal system with C 2/c space group. In the crystal structure, the intermolecular N–H···O hydrogen bonds link the molecules into infinite chains along the b-axis direction. The dominant interactions formed in the crystal packing were found to be hydrogen bonding and van der Waals interactions according to the Hirshfeld surface (HS) analysis. The evaluation of energy frameworks showed that stabilization of the compound was dominated by dispersion energy contribution. The anticancer activity of the compound was tested by employing several cellular assays. The compound showed strong anticancer effects, with IC50 values of 85 µM for MCF7 cells and 115 µM for MDA-MB-231 cells, indicating dose-dependent suppression of cell viability, migration, and colony formation. Computational analyses indicated favorable binding of compound 2 to ERRγ and predicted good oral availability of the generated compound. Pathway analysis using KEGG pathways identified significant enrichment in pathways related to cancer. These results highlight the compound's promise as a potential treatment option for breast cancer, prompting further exploration in future studies.

Isolation, characterization, and analysis of pure compounds from Leea macrophylla leaf extract for antibacterial, antidiabetic, cytotoxicity and phytotoxicity

This research aims to isolate, characterize, and analyze pure compounds from Leea macrophylla leaf extract to investigate its antibacterial, antidiabetic, cytotoxic, and phytotoxic effects. Fresh leaves were collected, dried, and subjected to methanol extraction to obtain a crude extract. From the petroleum ether fraction (PEF) of this extract, three fractions—designated LM1, LM2, and LM3—were prepared using column chromatography. The fractions were tried to be characterized in search for single compound by instrumental technique like ATR-FTIR, 1H NMR and 13C NMR but the 1H NMR and 13C NMR spectra were found complex which were difficult to interpret. To dispel the doubt and get clear idea about the structure, GC-MS analysis of the compounds was carried out whose result showed that all the three extracts were decomposed to several small organic compounds that made the structure elucidation difficult. For this complication, the characterization of the extracts was not possible. Numerous compounds were identified in the methanol extract of L.macrophylla through GC-MS analysis. Among these compounds, Benzene, 1,2,3-trimethyl- and Undecane were found in higher percentages in LM1. LM2 contained Azulene and Bicyclo [4.4.1]undeca-1,3,5,7,9-pentaene, while LM3 was characterized by the presence of 9,9-Dimethoxybicyclo [3.3.1]nona-2,4-dione and 11-(2-Cyclopenten-1-yl)undecanoic acid, among others. The antibacterial activity of these fractions was evaluated against various bacterial strains, demonstrating broad-spectrum effectiveness. LM1 fraction showed the highest antibacterial activity against Proteus sp. With zone of inhibition 25 mm and weak activity against S. sonnei with zone of inhibition 5 mm. LM2 showed the highest activity to both E. cocci and P. aeruginosa with the zone of inhibition of 18 mm and comparatively lower but significant against Proteus sp. LM3 was highly active to S. sonnei with zone of inhibition 20 mm and lower but quite significant against Proteus sp. Moreover, the anti-diabetic potential was assessed, with LM1 showing the strongest α-amylase inhibitory activity, outperforming quercetin (standard). The IC50 values of LM1, LM2, LM3, and quercetin were 57.36 μg/mL, 100.66 μg/mL, 164.92 μg/mL, and 97.45 μg/mL, respectively. In addition, cytotoxicity was assessed using a brine shrimp lethality bioassay, and phytotoxicity was evaluated through seed germination and growth assays. The results suggest that L.macrophylla leaf extracts have potential applications in antimicrobial, antidiabetic, and anti-cancer contexts. This comprehensive study bridges gaps in knowledge surrounding L.macrophylla's multifaceted properties, offering insights into its therapeutic and ecological potential for healthcare and environmental management.

Efficient UV-Vis-NIR Responsive CO2 Reduction Photocatalyst with Black Pinecone-Shaped Carbon Nitride Loaded with Lanthanum Oxide.

Photothermal catalysis combines the advantages of photocatalysis and thermal activation, which provides a new research angle for CO2 catalytic reduction. In this study, Black carbon nitride with a three-dimensional (3D) pinecone-shaped structure (BPCN) was prepared by a simple solvothermal method using melamine as a precursor without the aid of a template. Lanthanum oxide doping on the BPCN catalysts (BPCN-La) was achieved by ultrasonic impregnation. This unique pinecone-shaped structure consists of self-assembled and interlaced carbon nitride rods (by SEM). The lanthanum element was distributed on the surface of the CN framework in the form of La2O3 (by XPS). The chemical structures of the samples were characterized by solid-state 13C nuclear magnetic resonance (13C NMR) and elaborated by density functional theory (DFT) analysis. This black carbon nitride expanded the light absorption band edge into the near-infrared (NIR) (300-1400 nm, by UV-vis absorption spectra) and had excellent photothermal conversion activity. La atom doping can significantly boost photogenerated electron excitation (by photocurrent test) and promote carrier separation and transfer (by PL). Upon incorporation of La atoms into BPCN, the highest occupied molecular orbital (HOMO) orbital is more concentrated on the oxygen atoms of La2O3. BPCN-La considerably narrowed the band gap width, exhibited an exceptional photothermal effect, and provided a large surface area, which significantly enhanced the photocatalytic reduction of CO2 reactions. The yields of CO reached 58.2 and 104.9 μmol·h-1·g-1 for BPCN and BPCN-La, respectively, with GCN as the control (6.3 μmol·h-1·g-1). Theoretical reaction pathways and selectivity for the photoreduction of CO2 on BPCN and BPCN-La were studied by DFT simulation. This work provides a new vision for the design of photothermal synergistic without extra-thermal input and full spectral response photocatalysts with high efficiency.

Molecular docking, ADME properties and synthesis of thiophene sulfonamide derivatives

This study investigates the drug-like properties of target molecules containing thiophene sulfonamide groups (7a–7s) using computational molecular docking techniques. The binding interactions of these derivatives were assessed using protein 2NSD (Enoyl acyl carrier protein reductase InhA, complexed with N-(4-methylbenzoyl)-4-benzylpiperidine, PDB DOI: 10.2210/pdb2NSD/pdb) as the receptor. Molecular docking results revealed notable docking scores for all compounds, ranging from −6 to −12 kcal/mol. Compounds 7e, 7i, and 7f, in particular, demonstrated impressive glide scores (>11 kcal/mol) and were selected for further analysis through molecular dynamics simulations, which provided deeper insights into their dynamic behavior and stability. The drug-like properties of these molecules were evaluated based on Lipinski’s Rule of Five and ADME (Absorption, Distribution, Metabolism, and Excretion) criteria and compared with known drugs. Additionally, we synthesized these target molecules (7a–7s) using Suzuki-Miyaura coupling with a nickel catalyst replacing palladium. The chemical structures of the synthesized compounds were confirmed through elemental analysis, LC-MS,1H-NMR, and 13C-NMR spectroscopy.

Carborane Conjugates with Ibuprofen, Fenoprofen and Flurbiprofen: Synthesis, Characterization, COX Inhibition Potential and In Vitro Activity.

The most effective anticancer drugs currently entail substantial and formidable side effects, and resistance of tumors to chemotherapeutic agents is a further challenge. Thus, the search for new anticancer drugs as well as novel therapeutic methods is still extremely important. Non-steroidal anti-inflammatory drugs (NSAIDs) can inhibit COX (cyclooxygenase), overexpressed in some tumors. Carboranes are emerging as promising pharmacophores. We have therefore combined both moieties in a single molecule to design drugs with a dual mode of action and enhanced effectiveness. The NSAIDs ibuprofen, flurbiprofen, and fenoprofen were connected with 1,2-dicarba-closo-dodecaborane(12) via methylene, ethylene or propylene spacers. Three sets of carborane-NSAID conjugates were synthesized and analyzed through multinuclear (1H, 11B, and 13C) NMR spectroscopy. Conjugates with methylene spacers exhibited the most potent COX inhibition potential, particularly conjugates with flurbiprofen and fenoprofen, displaying higher selectivity towards COX-1. Furthermore, conjugates with methylene and ethylene spacers were more efficient in suppressing the growth of human cancer cell lines than their propylene counterparts. The carborane-flurbiprofen conjugate with an ethylene spacer was the most efficient and selective toward the COX-2-negative cell line HCT116. Its mode of action was basically cytostatic with minor contribution of apoptotic cell death and dominance of cells trapped in the division process.

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.

Three new spirocyclic terpenoids from Euphorbia amygdaloides exhibit cytotoxicity against cancerous cell lines through early and late apoptosis

Bioassay-guided fractionation led to the isolation of three new spirocyclic terpenoid compounds from Euphorbia amygdaloides L., named Zagrosin I–III. Their structures were identified by 1D and 2D NMR (1H NMR, 13C NMR, DEPT 135, HMBC, and HSQC-TOCSY) and LC-MS-MS spectrometry. The cytotoxicity of the isolated spirocyclic terpenoids (Zagrosin I-III) was assessed against human breast cancer (MCF-7), human fibrosarcoma (HT1080), and normal human foreskin fibroblast cells with MTT assays (24, 48, and 72 h treatments). The FITC-Annexin V apoptosis flow cytometry assays and cell cycle analysis were performed for Zagrosin I–III.These isolated compounds were identified as: (9)-8a-((benzoyloxy)methyl)-2-methoxy-4,9-dimethyltetrahydro-4H,5H-2,4a-methanobenzo[d] [1,3] dioxine-4-carboxylate (Zagrosin I), ((9)-4-hydroxy-2-methoxy-4,9-dimethyltetrahydro-4H,8aH-2,4a-methanobenzo[d] [1,3] dioxin-8a-yl) methyl benzoate (Zagrosin II), and (9)-2-methoxy-4,9-dimethyl-8a-(phenoxy methyl) tetrahydro-4H,5H-2,4a-methanobenzo[d][1,3]dioxin-4-yl 4-methylpentanoate (Zagrosin III).The IC50 of Zagrosin I on 48-h-treated MCF-7 was calculated as 1.5 μg/mL. Zagrosin II and III exhibited cytotoxicity on 48-h-treated MCF-7 with IC50s of 14.04 and 12.50 μg/mL, respectively. The IC50 of Zagrosin I on human fibrosarcoma (HT1080) was 115.5 μg/mL, Zagrosin III, 16.81 μg/mL (48 h treatment), and Zagrosin II, 142.7 μg/mL (72 h treatment). Zagrosin I-III exhibited significant cytotoxicity against the MCF-7 cell line and human fibrosarcoma (HT1080), with the mechanism of early and late apoptosis affecting cells mostly in G0/G1 fallowed by S and G2 phases. MCF-7 had a higher rate of phosphatidyl serine exposure on the cell membrane than two other studied cells. The cytotoxicity on normal human foreskin fibroblasts was low. Zagrosin I-III can be considered an effective chemical backbone for anticancer drug development.Abbreviations: 2D NMR: Two-Dimensional Nuclear Magnetic Resonance Spectroscopy; API: Atmospheric Pressure Ionization; DEPT: Distortionless Enhancement by Polarization Transfer; ELISA: Enzyme-Linked Immunosorbent assay; ERK: Extracellular signal-regulated kinase; ESI: Electrospray ionization; FBS: Fetal Bovine Serum; FITC: Fluorescein isothiocyante; fr: fraction; HMBC: Heteronuclear Multiple Bond Correlation; HPLC: High-Performance Liquid Chromatography; HSQC: Heteronuclear Single Quantum Coherence; HT1080: Human fibrosarcoma cell line; IC50: Half-maximal inhibitory concentration; MCF-7: Human breast cancer cell line; MHz: Megahertz; MTT: 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide; NMR: Nuclear Magnetic Resonance; PBS: Phosphate Buffered Saline; PI: Propidium Iodide; ppm: Part Per Million; Rf: Retention Factor; TLC: Thin-layer chromatography; TOCSY: Total Correlation Spectroscopy; VLC: Vacuum Liquid Chromatography.