Journal of Molecular Structure最新文献

{"title":"In-silico studies of 3-tert-butyl-7-[2-phenyl ethenyl]-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4] triazin-4-one as a Potential SARS-CoV-2 Inhibitor: Insights from an experimental and computational approach","authors":"Chandra ,&nbsp;T.N. Lohith ,&nbsp;B.H. Gayathri ,&nbsp;Mehran Feizi-Dehnayebi ,&nbsp;Karthik V． ,&nbsp;Shamantha Kumar ,&nbsp;K. Divya ,&nbsp;M.A. Sridhar ,&nbsp;M. Mahendra ,&nbsp;Ghodsi Mohammadi Ziarani","doi":"10.1016/j.molstruc.2025.141356","DOIUrl":"10.1016/j.molstruc.2025.141356","url":null,"abstract":"<div><div>The novel thiadiazole-triazine derivative <em>3-tert-butyl-7-[2-phenyl ethenyl]-4H-[1,3,4]thiadiazolo[2,3-c][1,2,4] triazin-4-one</em> (<strong>TCA1</strong>) has been synthesized and characterized spectroscopically. The molecular structure of the compound has been determined by single crystal X-ray diffraction (XRD) study. Hirshfeld surface analysis was carried out to know the various non-covalent interactions present in the crystal. Also, density functional theory (DFT) calculations were performed to explore the electronic properties of the molecule and various physicochemical properties of the compound (<strong>TCA1</strong>), which were correlated well with the results finding from XRD. Frontier molecular orbitals (FMO) analysis, Molecular Electronic Potential (MEP), and quantum chemical reactivity analyses have been performed. Further, Molecular docking analysis was carried out to elucidate the binding ability of <strong>TCA1</strong> with Omicron version of SARS-COV-19 spike protein. The binding efficacy of <strong>TCA1</strong> with the molecular targers was compared with that of remdesivir (SARS-CoV-2). The molecular docking study was validated by molecular dynamics simulation study of Omicron version of SARS-COV-19 spike protein.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1330 ","pages":"Article 141356"},"PeriodicalIF":4.0,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143454378","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":"Antihyperglycemic hydantoin derivative: Design, molecular docking, synthesis, crystal structure, computational studies, pharmacological and toxicological activities","authors":"Walid Guerrab ,&nbsp;Salma Mortada ,&nbsp;Abderrazzak El Moutaouakil Ala Allah ,&nbsp;Güneş Demirtaş ,&nbsp;Joel T. Mague ,&nbsp;Abdullah Yahya Abdullah Alzahrani ,&nbsp;Mohammed H. AL Mughram ,&nbsp;My El Abbes Faouzi ,&nbsp;Youssef Ramli","doi":"10.1016/j.molstruc.2025.141802","DOIUrl":"10.1016/j.molstruc.2025.141802","url":null,"abstract":"<div><div>The phenytoin-derived compound 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)-N-(4-methoxyphenyl)acetamide referred to as <strong><em>Cpd3</em></strong>, investigated in this paper, was studied using Density Functional Theory (DFT) with the B3LYP method and 6–311++G(d,p) basis set, and its theoretical structure was validated against the experimental one. Frontier Molecular Orbitals (FMOs) analysis determined the energy gap between LUMO and HOMO, while a Molecular Electrostatic Potential (MEP) map identified nucleophilic and electrophilic regions. Hirshfeld Surface (HS) analysis examined intermolecular interactions. Then Molecular docking revealed strong binding affinities for α-glucosidase and α-amylase, with binding energies of -7.2 and -7.8 kcal/mol, respectively. These interactions were stabilized by various bonds, including hydrogen bonds and aromatic interactions. <em>In vitro,</em> the newly synthesized compound was evaluated for its antidiabetic activity against α-glucosidase and α-amylase enzymes and for antioxidant activity by utilizing several tests as DPPH (1, 1-diphenyl-2-picryl hydrazyl), ABTS (2, 2′-azino-bis(3-ethyl benzthiazoline-6-sulfonicacid) and reducing power test (FRAP). Hydrolase enzyme inhibition assays showed potent inhibitory effects, with an IC50 of 43.58 ± 1.02 µM for α-glucosidase and 108.28 ± 1.20 µM for α-amylase, comparable to the standard drug approved Acarbose. These findings suggest <strong><em>Cpd3</em></strong> as a promising candidate for antihyperglycemic therapy.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141802"},"PeriodicalIF":4.0,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143453344","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":"NaLaCaWO6 double perovskite: Structure analysis, efficient Bi3+ to Eu3+ energy transfer and favourable visual optical thermometry","authors":"Xuyan Xue ,&nbsp;Sihan Yang ,&nbsp;Weigang Liu ,&nbsp;Liang Dong ,&nbsp;Qi Zhu ,&nbsp;Xuejiao Wang ,&nbsp;Ji-Guang Li","doi":"10.1016/j.molstruc.2025.141797","DOIUrl":"10.1016/j.molstruc.2025.141797","url":null,"abstract":"<div><div>Herein, we report a series of NaLaCaWO₆: Bi³⁺, Eu³⁺ double perovskite phosphors with a monoclinic crystal structure, achieving high-precision optical thermometry. Comprehensive characterisations, including X-ray diffraction, Raman spectroscopy, X-ray photoelectron spectroscopy, scanning electron microscopy and thermoluminescence, revealed detailed material properties. The electronic structure and formation energies of NaLaCaWO₆: Bi³⁺, Eu³⁺ were calculated using density functional theory (DFT), and the influence of luminescent centers (Bi³⁺ and Eu³⁺) on the optical properties was analyzed. The emission colour was tuned from green to red with increasing Eu³⁺, and efficient Bi³⁺ → Eu³⁺ energy transfer was achieved through dipole–dipole interaction, with an energy transfer efficiency of 59.4 %. In addition, the distinct temperature response characteristics of Bi³⁺ and Eu³⁺ fulfilled the prerequisites for efficient temperature signal resolution, demonstrating a high relative sensor sensitivity of 0.74 % K⁻¹ (at 298 K) and minimal temperature resolution (δ<em>_T</em> = 0.14 K) for the NaLaCaWO₆: 0.05Bi³⁺, 0.01Eu³⁺. The moisture resistance of the phosphor was confirmed through a water immersion test, demonstrating excellent moisture resistance. These findings not only elucidate the photoluminescence behaviour of Bi³⁺ and Eu³⁺ in NaLaCaWO₆ but also highlights its promising application prospects in optical thermometry.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141797"},"PeriodicalIF":4.0,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463469","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":"Optimizing 3-MeO-BTFMAN thin films: Structural insights and photonic performance for advanced optoelectronic applications","authors":"Leyla Babali Özen ,&nbsp;Gül Yakalı ,&nbsp;Furkan Özen ,&nbsp;Öner Ekici ,&nbsp;Bayram Gündüz ,&nbsp;Günseli Turgut Cin ,&nbsp;Muhittin Aygün","doi":"10.1016/j.molstruc.2025.141793","DOIUrl":"10.1016/j.molstruc.2025.141793","url":null,"abstract":"<div><div>Thin films of 2-(3,5-Bistrifluoromethylphenyl)-3-(3-Methoxyphenyl)acrylonitrile (3-MeO- BTFMAN) were prepared with different film thicknesses (8.51 µm, 16.72 µm, and 27.06 µm) using the spin-coating method, with DMSO as the solvent. The photonic properties and refractive indices of the prepared 3-MeO-BTFMAN solution and films were thoroughly investigated using a combination of experimental and theoretical methods. However, as the effect of film thickness on photonic properties could not be explored using Density Functional Theory (DFT) method, this aspect was analyzed solely through experimental approaches. The molecular structure of the 3-MeO-BTFMAN compound was analyzed through a combination of theoretical calculations using the DFT method and experimental analyses involving via X-ray diffraction and spectroscopic techniques. Results showed that the optical band gap of the 3- MeO-BTFMAN film decreased from 3.268 eV to 3.199 eV with increasing film thickness, which demonstrates the impact of film thickness on photonic properties. Additionally, the refractive index of the film exhibited normal dispersion behavior. These findings suggest that the 3-MeO-BTFMAN films hold promise for applications in optoelectronic devices.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141793"},"PeriodicalIF":4.0,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143464279","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":"Synthesis, antimicrobial activity, molecular docking and molecular dynamics studies of novel bioactive compounds derived from propylthiouracil","authors":"Mostafa Ahmed ,&nbsp;Mahmoud M. Hamed ,&nbsp;Mostafa Sayed ,&nbsp;Ahmed A. El-Rashedy ,&nbsp;Adel M. Kamal El-Dean ,&nbsp;Mohammad H.A. Hassan ,&nbsp;Mohamed F. Mady ,&nbsp;Mahmoud S. Tolba","doi":"10.1016/j.molstruc.2025.141779","DOIUrl":"10.1016/j.molstruc.2025.141779","url":null,"abstract":"<div><div>Propylthiouracil (PTU) and its derivatives exhibit a wide range of biological activities, making them valuable compounds in pharmacology and medicinal chemistry. In the present work some new heterocyclic compounds (<strong>2</strong>–<strong>9</strong>) were synthesized through multi steps using propylthiouracil (PTU) <strong>1</strong> as starting material. The claimed chemical structures of all new synthesized compounds were elucidated by spectral analysis including FTIR, NMR and Mass spectroscopy. Furthermore, the antimicrobial activity for all synthesized compounds were investigated against different strains of bacteria and fungi. The results suggested that compounds <strong>3, 5, 6a, 6b, 6c, 7b</strong> demonstrate positive results against the Fluconazole\" as the antifungal positive control, while compounds <strong>5, 6a 6c, 8</strong> show positive results against Cefotaxime\" as the antibacterial positive control. Moreover, molecular dynamic simulations revealed that compound <strong>5</strong> demonstrated significant interactions with essential residues of the binding site, resulting in a stable complex throughout the entire simulation run.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141779"},"PeriodicalIF":4.0,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452811","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":"Synthesis, characterization of europium(III) and terbium(III) complexes containing lawsone ligand and their interaction with DNA, HSA, and topoisomerases","authors":"Josias S. Rocha ,&nbsp;George B.S. Pereira ,&nbsp;Marcos V. Palmeira-Mello ,&nbsp;Willyan F. Oliveira ,&nbsp;Jocely L. Dutra ,&nbsp;Tamara Teixeira ,&nbsp;Nádija N.P. da Silva ,&nbsp;Gabriela P. Oliveira ,&nbsp;Paulo C. Gomes-Junior ,&nbsp;Anna C.S.J. Passaes ,&nbsp;João H. Araujo-Neto ,&nbsp;Alzir A. Batista ,&nbsp;Javier Ellena ,&nbsp;José D.L. Dutra ,&nbsp;Renan L. Farias ,&nbsp;Fillipe V. Rocha","doi":"10.1016/j.molstruc.2025.141790","DOIUrl":"10.1016/j.molstruc.2025.141790","url":null,"abstract":"<div><div>In this study, two complexes based on Europium [Eu(LAW)₃(H₂O)₃] <strong>(1)</strong> and Terbium [Tb(LAW)₃(H₂O)₃] <strong>(2)</strong>, each containing the lawsone ligand, were synthesized and comprehensively characterized using Infrared and UV-Visible spectroscopies, Cyclic Voltammetry, Conductivity, and Magnetic Susceptibility measurements. Crystal structure information was determined via X-ray diffraction (XRD), and elemental analysis confirmed the compounds’ purity. Experimental and theoretical UV-Vis data were compared through TD-DFT calculations, providing insights into the low luminescence of both Eu(III) and Tb(III) complexes, with excited states calculated both with and without solvent effects. DNA-binding experiments with ct-DNA were conducted using viscosity measurements, UV-Vis titrations, circular dichroism, and fluorescence competition assays to explore the complexes' primary interactions with the DNA target. Additionally, DNA cleavage properties were examined using pBR322 plasmid DNA with agarose gel electrophoresis. Although no cleavage activity was observed, DNA interaction studies suggested covalent binding, supported by viscosity and circular dichroism data. Furthermore, analyzing the docking results, both compounds demonstrated stable conformations within the Sudlow I site also the lawsone-based compounds demonstrated an ability to bind to human serum albumin (HSA) with binding constants (K_b) in the range of 10⁵-10⁶ and showed Topoisomerase IIα inhibition at 50 µM. Both compounds remained stable for up to 48 hours.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141790"},"PeriodicalIF":4.0,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143463442","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":"Synthesis, computational analysis, and exploring antiproliferative activity of triazolo- and thiazolo-pyrimidine derivatives as potential EGFR inhibitors","authors":"Ali H. Abdelrahman ,&nbsp;Mohammad E. Azab ,&nbsp;Mohamed A. Hegazy ,&nbsp;Ahmed Labena ,&nbsp;Abdullah Y.A. Alzahrani ,&nbsp;Sayed K. Ramadan","doi":"10.1016/j.molstruc.2025.141789","DOIUrl":"10.1016/j.molstruc.2025.141789","url":null,"abstract":"<div><div>Anticancer drug acquiring usually discloses with an in vitro testing in cell panels to certainly detect the lead compounds. EGFR is a tyrosine kinase cell surface receptor that plays a key function in signal transduction processes and is observed on most cell surfaces. One of the promising frameworks in drug detection is pyrimidine and its fused heteroannulated bicyclic derivatives which exhibited promising anticancer activity. The prepared triazolopyrimidine and thiazolopyrimidine derivatives were proposed to fit into the ATP binding site of EGFR protein. The <em>in vitro</em> antiproliferative screening against MCF7 and HCT116 cancer cell panels disclosed the most influence of triazolopyrimidine <strong>3</strong>, thiazolopyrimidine <strong>9</strong>, and pyrimidinethione <strong>1</strong> compared to the reference drug, roscovitine (imidazopyrimidine hybrid). The inhibitory action of the most promising compounds was explored versus EGFR enzyme, which displayed the highest efficacy of triazolopyrimidine <strong>3</strong> compared to the standard drug (erlotinib). The structure-activity relationship (SAR) probe demonstrated that specific structural modifications had a significant impact on the antiproliferative action. <em>In silico</em> molecular docking was performed on these promising compounds versus EGFR enzyme (breast cancer protease, PDB ID: <span><span>3W32</span><svg><path></path></svg></span>) to show the enzyme-inhibitor interactions, which uncovered the superlative binding interactions of triazolopyrimidine <strong>3</strong> with key nucleobases and amino acids of EGFR kinase. Among DFT calculations, E_LUMO of compounds <strong>3</strong> <strong>&lt; 1</strong> <strong>&lt; 9</strong>, which enriched its binding affinity of with nucleophilic receptor's active pockets. Regarding ADME simulation, they had gastrointestinal tract (GIT) absorption, good bioavailability score, and worthy lead-likeness. This work may contribute to developing new effective EGFR inhibitor.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141789"},"PeriodicalIF":4.0,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143471305","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":"The liquid crystalline and optical properties of chiral symmetrical dimers with two azo groups and 1,2-propanediol chiral moiety","authors":"Yan Chen ,&nbsp;Yajuan Chen ,&nbsp;Niuniu Zhang ,&nbsp;Weijie Gao ,&nbsp;Jianshe Hu ,&nbsp;Guiyang Yan","doi":"10.1016/j.molstruc.2025.141794","DOIUrl":"10.1016/j.molstruc.2025.141794","url":null,"abstract":"<div><div>Six symmetric dimers were synthesised with 1,2-propanediol as the chiral center, azobenzene as the side arm, and substituents with different electron withdrawal ability groups ( C₄H₉O, C₂H₅O, CH₃O, H, F and CF₃) as the end groups. All dimers exhibit photoisomerism with E to Z isomerisation being much faster than Z to E. The end groups, which have different electron-donating and withdrawing abilities, significantly influence the liquid crystal and optical properties of the dimers. Specifically, E to Z photoisomerisation rates are faster for dimers with C₄H₉O, C₂H₅O, and CH₃O end groups than for those with H, F, and CF₃ end groups. The dimers with C₄H₉O, C₂H₅O and CH₃O end groups display a monotropic chiral nematic (N*) phase on cooling, while those with H, F, and CF₃ end groups do not exhibit liquid crystal properties. Notably, (CH₃O-Azoben-C₄)₂-PD shows obvious selective reflectivity in the visible light range on cooling. Using short alkyl chains (CH₃O) as terminal groups reduces the melting and crystallisation temperature and weakens the alternating arrangement of high and low polarisability, which is conducive to liquid crystal phase formation.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141794"},"PeriodicalIF":4.0,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143464287","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":"Synthesis, biological evaluation, ADMET studies, and molecular docking of novel coumarin–isoxazole derivatives as dual inhibitors of Hsp90 protein and acetylcholinesterase enzyme","authors":"Amina Benazzouz-Touami ,&nbsp;karima Ighilahriz ,&nbsp;Malika Makhloufi-Chebli ,&nbsp;Amina Chouh ,&nbsp;Nadia Hadhoum ,&nbsp;Jean-Bernard Behr","doi":"10.1016/j.molstruc.2025.141776","DOIUrl":"10.1016/j.molstruc.2025.141776","url":null,"abstract":"<div><div>In this work we designed and evaluated a new series of coumarin–isoxazole hybrids with the aim of combining their individual biological attributes into one single chemical structure. All newly synthesized derivatives <strong>3a-g</strong> were evaluated for their antioxidant activity using the CUPRAC method and tested for their <em>in vitro</em> anticholinesterase activity. The results showed that the synthesized compounds <strong>3b,3c</strong> and <strong>3f</strong> display significant antioxidant activity. Moreover, the coumarin-isoxazoles showed promising AChE inhibitory potential, making them valuable candidates for further investigations in the context of neurodegenerative disorders. Molecular modeling studies were conducted to dock the compounds into the Hsp90 protein, revealing a strong affinity for the active site. Additionally, physicochemical properties, drug-likeness, bioactivity scores, and Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) profiles were predicted. These assessments revealed that all compounds have favorable pharmacokinetic properties and were predicted to be non-carcinogenic.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141776"},"PeriodicalIF":4.0,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143464283","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":"Tetrahydropyrazolopyrazolones: Synthesis, X-ray crystallography and antimicrobial activity","authors":"Jovana P. Bugarinović ,&nbsp;Dragana Stevanović ,&nbsp;Marko S. Pešić ,&nbsp;Anka Todosijević ,&nbsp;Slađana Novaković ,&nbsp;Goran Bogdanović ,&nbsp;Vladimir Mihailović ,&nbsp;Jelena Katanić Stanković ,&nbsp;Ivan Damljanović","doi":"10.1016/j.molstruc.2025.141778","DOIUrl":"10.1016/j.molstruc.2025.141778","url":null,"abstract":"<div><div>1,3-Dipolar cycloaddition is a valuable reaction for synthesizing heterocycles which form the core of pharmacophores with diverse bioactivities. In this study, structurally intriguing <em>cis</em>/<em>trans</em> pairs of 6-acyl-5-aryltetrahydropyrazolo[1,2-a]pyrazol-1(5<em>H</em>)-ones were synthesized via the 1,3-dipolar cycloaddition of <em>N,N’</em>-cyclic azomethine imines and vinyl-containing enones to assess their antimicrobial activity. The crystal structures of two <em>cis</em> and two <em>trans</em> tetrahydropyrazolopyrazolone derivatives were analyzed and their geometrical features were compared with structurally related compounds from the Cambridge Structural Database (CSD). The antimicrobial activity evaluation of the synthesized tetrahydropyrazolopyrazolones against bacteria and fungi revealed weak to moderate efficacy, with minimum inhibitory concentration (MIC) values ranging from 2 to 8 mM for most species. Notably, the compounds exhibited a stronger inhibitory effect on mold growth compared to <em>Candida albicans</em>. Furthermore, the tested compounds demonstrated greater efficacy against Gram-positive bacteria than Gram-negative bacteria.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1333 ","pages":"Article 141778"},"PeriodicalIF":4.0,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143464284","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}