Journal of Molecular Structure最新文献

{"title":"Genipin-crosslinked biopolymer hydrogels for controlled quercetin delivery: Antibacterial activity, cytocompatibility and docking-assisted protein interaction","authors":"Gunasekaran Vidhyadevi,&nbsp;S.R. Suseem","doi":"10.1016/j.molstruc.2026.145521","DOIUrl":"10.1016/j.molstruc.2026.145521","url":null,"abstract":"<div><div>In this study, genipin-crosslinked hydrogel films composed of chitosan, poly (vinyl alcohol), and silk fibroin (GPQH) were developed to promote full-thickness wound healing and enable sustained delivery of the natural bioactive flavonoid quercetin (Q). GPQH films containing 1 %, 2 %, and 3 % (w/w) genipin were fabricated and systematically evaluated for their physicochemical properties, mechanical strength, antibacterial activity, biocompatibility, and quercetin release behaviour. Mechanical testing showed a significant improvement in tensile strength, increasing from 1.51 MPa for the neat hydrogel to 7.49 MPa for the 3 % GPQH film. The hydrogels also exhibited enhanced water absorption (52.6 ± 1.24 % to 90.4 ± 0.64 %) and increased water contact angle (5.8° to 29.4°), indicating improved hydrophilicity and moisture retention. Antibacterial assays against <em>Staphylococcus epidermidis</em> and <em>Proteus mirabilis</em> revealed progressively larger inhibition zones with increasing genipin concentration, reaching 14–15 mm for the 3 % GPQH film. Quercetin-loaded GPQH films demonstrated sustained and concentration-dependent release profiles, with the 2 % GPQH formulation providing the most controlled release over 48 h. Release kinetics were best described by the Higuchi diffusion model (R² = 0.9909), supported by the Korsmeyer–Peppas model (R² = 0.9792), indicating diffusion-dominated, non-Fickian transport. Cytotoxicity studies using an MTT assay on NIH-3T3 fibroblast cells confirmed excellent biocompatibility, with cell viability exceeding 90 % for all formulations. Additionally, molecular docking analysis predicted strong binding affinity (–9.0 kcal/mol) between quercetin and a wound-healing-related protein (PDB ID: 3SHI). Overall, the 2 % GPQH hydrogel film achieved an optimal balance of mechanical integrity, sustained bioactive release, antibacterial efficacy, and cytocompatibility, highlighting its potential as a multifunctional wound-healing dressing.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145521"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192479","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A bifunctional ligand-derived anionic metal-organic framework with 9-connected Ni3(μ3-OH) SBUs for efficient C2H6/C2H4 separation","authors":"Ping Zhang,&nbsp;Qin-Wen Shi,&nbsp;Wen-Yuan Wu,&nbsp;Jun-Feng Bai","doi":"10.1016/j.molstruc.2026.145545","DOIUrl":"10.1016/j.molstruc.2026.145545","url":null,"abstract":"<div><div>An anionic 3D MOF featuring 9-connected Ni₃(<em>μ</em>₃-OH) secondary building units (SBUs), (Me₂NH₂)₂[Ni₆(OH)₂(Bpdc)₃(4-Ptz)₆]·11H₂O (NJTU-Bai90; NJTU-Bai denotes Nanjing Tech University Bai’s group), was hydrothermally synthesized using the bifunctional ligands bicyclo[1.1.1]pentane-1,3-dicarboxylic acid (H₂Bpdc) and 4-(2H-tetrazol-5-yl)pyridine (4-HPtz). This MOF crystallizes in <em>I-43</em> <em>m</em> space group and possesses intersecting 3D channels packed by trigonal-pyramidal and tetrahedral cages. Tailored for reversible C₂H₆ adsorption and one-step purification of polymer-grade C₂H₄, NJTU-Bai90 not only has a high BET surface area of 1465.7 m² g⁻¹ but also exhibits excellent stability in aqueous solutions at room temperature for at least one month. NJTU-Bai90 exhibits superior C₂H₆ uptake (97.6 cm³ g⁻¹ at 298 K and 82.5 cm³ g⁻¹ at 308 K, both measured at 1 bar) in comparison with C₂H₄ (85.5 cm³ g⁻¹ at 298 K and 68.4 cm³ g⁻¹ at 308 K, both measured at 1 bar). Remarkable IAST selectivity values (1.51 and 1.56, respectively) are maintained even at elevated temperatures. Furthermore, dynamic breakthrough experiments demonstrate that a C₂H₆/C₂H₄ mixture (1/15, v/v) can be efficiently separated in one step and that polymer-grade C₂H₄ yielding with a productivity of 19.1 mL g⁻¹ at 298 K and 1 bar. The distinct retention times of C₂H₆ and C₂H₄ on NJTU-Bai90-packed separation columns further highlight the material’s great potential for industrial gas separation applications.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145545"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192481","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A novel NLO active 4-bromoanilinium hydrogen malonate single crystal: Experimental and theoretical analysis of structural, spectral, topological and Z-scan properties","authors":"D. Beryl Jacksy ,&nbsp;D. Arul Dhas ,&nbsp;I. Hubert Joe ,&nbsp;G. Vinitha","doi":"10.1016/j.molstruc.2026.145564","DOIUrl":"10.1016/j.molstruc.2026.145564","url":null,"abstract":"<div><div>The novel organic single crystal 4-Bromoaniline hydrogen malonate (4-BRMAL) was grown using methanol with slow evaporation method. The crystal was analysed using UV–Vis, FT-IR, FT-Raman spectra and single-crystal diffraction. Theoretical calculations were performed using density functional theory (DFT) with the B3LYP/6–31G(d, p) basis set. These studies were aimed to investigate the molecular structure and vibrational frequencies of 4-BRMAL. Natural bond orbital (NBO) and natural charge analysis (NCA) have provided a detailed evaluation of the compound’s stability by confirming the presence of both intra and intermolecular interactions. UV–visible spectroscopy revealed electronic transitions with a lower cut-off wavelength of 263 nm, while fluorescence spectroscopy demonstrated yellow and an orange emission spectra at 591 nm, indicating its potential for NLO applications. TG/DTA showed thermal stability up to 149.80 °C with significant weight loss of 4-BRMAL. Hirshfeld surface analysis and two-dimensional fingerprint plots identified key atomic interactions in the crystal packing. The frontier molecular analysis showed a 4.78 eV energy gap indicating significant charge transfer characteristics. Electron-hole distribution, interatomic interaction (IRI) and atoms in molecule (AIM) analysis revealed strong hydrogen bonding and electron delocalization confirming the compound's favorable electronic structure. Density of states (DOS) analysis further highlighted the potential for non-linear optical (NLO) applications. Theoretical NLO calculations indicated a second-order hyperpolarizability of 561.33 <span><math><mo>×</mo></math></span> 10⁻³⁰ e.s.u, demonstrating 4-BRMAL’s suitability for optoelectronic device applications. Z-scan analysis confirmed that 4-BRMAL is a promising potential candidate for NLO activity with a third-order hyperpolarizability of 6.05 × 10⁻⁶ e.s.u. These analyses suggest that the title compound 4-BRMAL is a promising candidate for optoelectronics and NLO devices.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145564"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Adamantane-tetrazole hybrid derivatives: Synthesis, crystal structure, molecular docking, molecular dynamics simulations and in vitro evaluation of antibacterial, antifungal, and anti-proliferative activities","authors":"Eman T. Warda ,&nbsp;Mahmoud B. El-Ashmawy ,&nbsp;Mohammed S.M. Abdelbaky ,&nbsp;El-Sayed E. Habib ,&nbsp;Santiago Garcia-Granda ,&nbsp;Annesha Chakraborty ,&nbsp;Subbiah Thamotharan ,&nbsp;Ali A. El-Emam","doi":"10.1016/j.molstruc.2026.145551","DOIUrl":"10.1016/j.molstruc.2026.145551","url":null,"abstract":"<div><div>A series of adamantane-tetrazole hybrid derivatives was synthesized and their structures were confirmed by ¹H NMR, ¹³C NMR and by X-ray crystallography. The <em>in vitro</em> antimicrobial activities of the synthesized compounds were evaluated against eight Gram-positive and Gram-negative bacteria, and pathogenic fungi. Compound <strong>5b</strong> exhibited notable antibacterial activity, particularly against <em>Staphylococcus aureus</em> and <em>Escherichia coli.</em> In addition, optimal anti-proliferative activity was demonstrated by compound <strong>5c</strong>, which showed potent inhibitory activity against all tested human cancer cell lines. The crystal structure of the potent compound <strong>5c</strong> crystallized in the triclinic system with space group <em>P</em>-1 and is stabilized by a network of C–H···N, C–H···S, and C–H···π interactions. Molecular docking analysis revealed that compound <strong>5c</strong> exhibits good binding affinity toward the DHFR and ERα receptors. Compound <strong>5a-c</strong> exhibited encouraging physicochemical properties and drug-likeness as potential antibacterial and/or anti-proliferative agents.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145551"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192497","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Role of inorganic ions in the photocatalytic performance of Cu(I)/Cu(II) metal-organic framework nanosheets","authors":"Shixiong Li ,&nbsp;Wei Guo ,&nbsp;Chuqing Zhang ,&nbsp;Xueling Liu ,&nbsp;Qiaoping Kong","doi":"10.1016/j.molstruc.2026.145646","DOIUrl":"10.1016/j.molstruc.2026.145646","url":null,"abstract":"<div><div>The field of photocatalysis has long been constrained by two core challenges: insufficient utilization of visible light and low charge-separation efficiency. In this study, a two-dimensional Cu(I)/Cu(II) metal-organic framework (MOF), [Cu₃(L)₂(ClO₄)(H₂O)₄]_n (<strong>Cu₃−MOF</strong>), was synthesized <em>in-situ</em> using 2-hydroxyisophthalic acid (H₂L) and Cu(ClO₄)₂·6H₂O as precursors. The TEM, AFM, and UV–Vis absorption spectroscopy revealed that the obtained <strong>Cu₃−MOF</strong> nanosheets (<strong>Cu₃−MOF-N</strong>), with a particle diameter of approximately 50 nm, exhibit strong visible-light absorption and an estimated band gap of 2.50 eV. <strong>Cu₃−MOF-N</strong> exhibited superior photocatalytic activity in methylene blue (MB) degradation, with degradation rates 7.34 and 1.63 times higher than those of P25 and UiO-66-NH₂, respectively, ranking it among the most active MOF photocatalysts. Co-existing inorganic ion experiments further indicated that Fe³⁺ and NO₃⁻ could enhance MB degradation by synergistically promoting ·OH generation, whereas Na⁺, K⁺, Ca²⁺, Cl⁻, SO₄^2- and PO₄^3- inhibited the degradation process through various mechanisms.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145646"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192666","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Elucidating the temperature-dependent structural and optoelectronic properties of Ag4V2O7 microhexagons","authors":"A.W. Miranda ,&nbsp;F.F. Sousa ,&nbsp;Thiago M.B.F. Oliveira ,&nbsp;M.L. Vega ,&nbsp;C. Luz-Lima ,&nbsp;J.S. Silva ,&nbsp;J.V.B. Moura ,&nbsp;A.S. de Menezes ,&nbsp;P.T.C. Freire ,&nbsp;G.S. Pinheiro","doi":"10.1016/j.molstruc.2026.145579","DOIUrl":"10.1016/j.molstruc.2026.145579","url":null,"abstract":"<div><div>Silver pyrovanadate (Ag₄V₂O₇) microhexagons were synthesized by coprecipitation and characterized to investigate their temperature-dependent structural and optoelectronic properties. The information framework was obtained by powder X-ray diffraction, differential scanning calorimetry, scanning electron microscopy, UV–visible spectroscopy, Raman spectroscopy, and Fourier-transform infrared spectroscopy, and is discussed in detail throughout this article. In summary, the data indicated that the orthorhombic phase (<em>Pbca</em> space group) of Ag₄V₂O₇ with microhexagonal morphology and 2.15 eV band-gap was produced, maintaining the synthesis conditions at 298 K. The Ag₄V₂O₇ phase undergoes a complete and irreversible phase transition to the monoclinic <em>β</em>-AgVO₃ phase when exposed to laser excitation power ≥ 6.16 <em>m</em>W. Additionally, two exothermic events were identified at 543 and 658 K, corresponding to the parallel formation of vanadium oxide and the subsequent melting of this material, respectively. In contrast, the material demonstrated good structural stability at low temperatures (135 - 300 K). Upon cooling back to room temperature (298 K), the sample recrystallized as a mixture of Ag₄V₂O₇ and vanadium oxide. Furthermore, the structural robustness and thermal responsiveness exhibited by Ag₄V₂O₇ microhexagons complement the database on this ceramic material with innovative insights, in addition to making it a strong candidate for advanced optoelectronic devices.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145579"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192447","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Solid-state structure and physicochemical characterization of the hydrocortisone–β-cyclodextrin inclusion complex","authors":"Aleksandra Kowalska ,&nbsp;Łukasz Szeleszczuk ,&nbsp;Kostas Bethanis ,&nbsp;Elias Christoforides ,&nbsp;Marta K. Dudek ,&nbsp;Monika Zielińska-Pisklak ,&nbsp;Dariusz Maciej Pisklak","doi":"10.1016/j.molstruc.2026.145607","DOIUrl":"10.1016/j.molstruc.2026.145607","url":null,"abstract":"<div><div>The inclusion complex formed between hydrocortisone and β-cyclodextrin was successfully obtained and structurally characterized in the solid state. Single-crystal X-ray diffraction provided direct evidence of hydrocortisone encapsulation within the β-cyclodextrin cavity, revealing a 2:1 host–guest stoichiometry and positional disorder of the guest molecules accommodated within head-to-head β-cyclodextrin dimers. The crystal packing adopts a channel-type arrangement stabilized by intermolecular hydrogen bonding and hydration networks. Complementary solid-state techniques, including PXRD, DSC–TGA, FT-IR spectroscopy, cryo-SEM, and ¹³C CP/MAS NMR, confirmed the formation of a distinct solid phase with reduced crystallinity and altered physicochemical properties compared with the parent compounds and their physical mixture. Periodic density functional theory calculations supported the experimental structure, demonstrating that the two crystallographically observed guest orientations represent energetically accessible configurations. Together, these results provide a comprehensive structural description of the hydrocortisone–β-cyclodextrin inclusion complex and clarify the molecular basis of its solid-state organization.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145607"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structure-guided design and synthesis of selective butyrylcholinesterase inhibitors","authors":"Christine Shing Wei Law ,&nbsp;Zhe Ying Ha ,&nbsp;Xavier Brazzolotto ,&nbsp;Keng Yoon Yeong","doi":"10.1016/j.molstruc.2026.145611","DOIUrl":"10.1016/j.molstruc.2026.145611","url":null,"abstract":"<div><div>Alzheimer’s disease (AD) is a progressive neurodegenerative disorder marked by cognitive and non-cognitive decline. Cholinesterase inhibitors remain among the few available treatments, acting by preventing the hydrolysis of acetylcholine to alleviate cholinergic deficits. As butyrylcholinesterase (BChE) activity progressively increases in advanced AD while acetylcholinesterase activity declines, selective BChE inhibition has emerged as a promising therapeutic approach. Benzimidazole is a versatile pharmacophore with diverse biological activities, including cholinesterase inhibition. This study aimed to develop more potent benzimidazole-based cholinesterase inhibitors by modifying the 1- and 2-positions of the benzimidazole core. Among the synthesized compounds, <strong>5IIa</strong> exhibited the most potent selective BChE inhibition at a low micromolar level (IC₅₀ = 0.4 μM). Human BChE (<em>h</em>BChE) was co-crystallized with <strong>5IIa</strong> to resolve the structure of the protein–ligand complex by X-ray crystallography. Owing to its labile nature, <strong>5IIa</strong> was subsequently modified to yield a series of derivatives (<strong>5IIa1</strong>–<strong>7</strong>), which demonstrated potent and selective inhibition of equine BChE (<em>eq</em>BChE), with IC₅₀ values ranging from 1.07 to 7.86 μM. Lead compound <strong>5IIa6</strong> inhibited <em>h</em>BChE with an IC₅₀ of 5.9 μM and was identified as a mixed-mode inhibitor based on kinetic studies. <strong>5IIa6</strong> was also predicted to have high blood-brain barrier permeability in an <em>in vitro</em> model, while cell viability assay against neuroblastoma and microglial cells indicated no significant toxicity. Taken together, these findings identify <strong>5IIa6</strong> as a promising and selective BChE inhibitor that warrants further investigation as a potential therapeutic agent for AD.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145611"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192402","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Experimental and theoretical aspects of Hydroxyarylbenzimidazole (HABI) as an effective corrosion sensor and inhibitor in different corrosive environments","authors":"Sonia Rani ,&nbsp;Vijay Luxami ,&nbsp;Shweta Goyal","doi":"10.1016/j.molstruc.2026.145538","DOIUrl":"10.1016/j.molstruc.2026.145538","url":null,"abstract":"<div><div>Hydroxy-aryl benzimidazole (<strong>HABI</strong>) organic molecule has been synthesised and explored as a corrosion sensor and inhibitor for steel in different corrosive environments (acidic and basic). The sensing behaviour of the molecule was studied by UV-Vis and fluorescence spectroscopy, and corrosion inhibition efficiency was investigated through gravimetric, electrochemical measurements and theoretical studies. <strong>HABI</strong> fluorescence is turned off in the presence of Fe³⁺ due to the formation of the <strong>HABI</strong>-Fe³⁺ complex. In both acidic (97.4%) and basic (87.5%) environments, more than 85% corrosion inhibition efficiency at <strong>1.0 mM</strong> was achieved through gravimetric and electrochemical studies. The inhibitor acts on both anodic and cathodic sites and the value of <span><math><mrow><mstyle><mi>Δ</mi></mstyle><msubsup><mi>G</mi><mrow><mi>a</mi><mi>d</mi><mi>s</mi></mrow><mn>0</mn></msubsup></mrow></math></span> -37.7 (acidic) and -31.8 (basic) KJmol^-1 proposed the adsorption of inhibitor on the steel surface through physio-chemisorption. The surface analysis used microscopic and spectroscopic techniques like FE-SEM, FTIR, and XPS, they suggest that inhibitor form protective layer on the steel surface. The binding mechanism of the <strong>HABI</strong> inhibitor with Fe³⁺ was investigated through DFT studies, providing HOMO-LUMO gap of 4.42 eV for inhibitor that reduces significantly to 1.80 eV upon binding with Fe³⁺ proving the efficient corrosion inhibition mechanism through charge transfer that agreed with experimental results. Practical application on the steel sample coated with <strong>HABI</strong> was done and obtained excellent corrosion inhibition (99%) efficiency.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145538"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192405","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Flavones with bulky pyrrole substituents: Synthesis, physicochemical characteristics and potential applications in medicine","authors":"Stepan Sysak ,&nbsp;Barbara Wicher ,&nbsp;Malgorzata Kucinska ,&nbsp;Pawel Bakun ,&nbsp;Joanna Kuzminska ,&nbsp;Philippe Grellier ,&nbsp;Roman Lesyk ,&nbsp;Anna Jelinska ,&nbsp;Ewa Tykarska ,&nbsp;Marek Murias ,&nbsp;Tomasz Goslinski ,&nbsp;Wojciech Szczolko","doi":"10.1016/j.molstruc.2026.145577","DOIUrl":"10.1016/j.molstruc.2026.145577","url":null,"abstract":"<div><div>This study presents the synthesis, physicochemical characterisation, and biological evaluation of a series of novel pyrrole-substituted flavone derivatives with potential therapeutic applications. Phenylated and halogenated pyrrole derivatives of flavones were obtained via Paal–Knorr condensation of 6- and 7-aminoflavones with various 1,4-diketones and their subsequent halogenation. The physicochemical properties and chemical structures of the novel compounds were confirmed using UV–VIS and NMR spectroscopy, mass spectrometry, X-ray diffraction and thermal analyses. Crystallographic studies revealed distinct packing motifs, with halogenated derivatives demonstrating recurring structural patterns and isostructurality, suggesting a crucial role of halogen bonding in crystal organisation. A combination of X-ray powder diffraction and thermal analyses confirmed the purity and stability of the compounds. Biological screening against <em>Plasmodium falciparum</em> identified 2-phenyl-7-(2,3,5-triphenylpyrrol-1-yl)chromen-4-one as the most potent antiplasmodial agent with the IC₅₀ value of 1.37 µg/ml, whereas moderate activity was noted for 2-phenyl-6-(2,3,5-triphenylpyrrol-1-yl)chromen-4-one and other analogues. Preliminary cytotoxicity assays on the human bladder cancer 5637 cell line revealed that halogen substitution at position 6 of the flavone scaffold, particularly in 6-(3,4-diiodo-2,5-dimethyl-pyrrol-1-yl)-2-phenyl-chromen-4-one, significantly increased cytotoxic potential (IC₅₀ &lt; 5 µM), albeit with limited selectivity toward non-cancerous cells. Overall, these findings highlight the importance of structural modifications in influencing biological activity and suggest that selected pyrrole-flavone derivatives, especially 2-phenyl-7-(2,3,5-triphenylpyrrol-1-yl)chromen-4-one and 6-(3,4-diiodo-2,5-dimethyl-pyrrol-1-yl)-2-phenyl-chromen-4-one, may serve as promising scaffolds for further optimisation as antiparasitic and anticancer agents.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1360 ","pages":"Article 145577"},"PeriodicalIF":4.7,"publicationDate":"2026-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146192491","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}