Journal of Molecular Structure最新文献

{"title":"Three benzo-nitrogen-containing heterocyclic probes for gradually improving the activity of γ-Glutamyltranspeptidase detection and its application","authors":"Xiaoming Wu ,&nbsp;Leyuan Ding ,&nbsp;Shaoxiang Yang,&nbsp;Hongyu Tian,&nbsp;Baoguo Sun","doi":"10.1016/j.molstruc.2025.141587","DOIUrl":"10.1016/j.molstruc.2025.141587","url":null,"abstract":"<div><div>Three benzo-nitrogen-containing heterocyclic probes with continuously tuned characteristics were designed to detect γ-Glutamyltranspeptidase (GGT) activity. The specific recognition site is the γ-glutamine bond, which is a specific chemical bond, and the activity of GGT leads to the hydrolysis of this bond. Probe 1 was synthesized by designing ' d-π-A ' structure and using benzimidazole acetonitrile as a fluorescent group. The UV absorption change was obvious and the fluorescence intensity was extremely weak. The detection limit was as low as 0.0608 U/mL. Under natural light, the probe solution gradually changed from colorless to slightly yellow with the increase of GGT activity. The benzo-pyrrole acetonitrile with weak charge transfer was used as the fluorescent group to synthesize probe 2, and the fluorescence intensity quenching was obvious, its detection limit was 0.244 U/mL. By designing ' d-π-A ' structure and benzothiazole with strong charge transfer ability was used as a fluorescent group to design and synthesize probe 3, and the fluorescence enhancement was more obvious. The solution gradually changed from colorless to blue under 365 nm UV irradiation. The enzymatic hydrolysis of probe 2, probe 3 take 25 mins to complete. In addition, the B value of probe 1, probe 3 solution and the G value of probe 2 solution were linearly connected with GGT activity, respectively. At the same time, it was found that the GGT activity of probe 2 and probe 3 had a linear correlation with △E, while probe 1 did not. Therefore, by optimizing the fluorescent group, the performance of the probe and the detection effect are improved. These three probes can be used as a practical tool for identifying GGT activity.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141587"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195534","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 and computational insight into the reactivity of chromium isoporphyrins","authors":"Debashis Bora ,&nbsp;Prakash J. Saikia ,&nbsp;Jagannath Bhuyan","doi":"10.1016/j.molstruc.2025.141603","DOIUrl":"10.1016/j.molstruc.2025.141603","url":null,"abstract":"<div><div>The synthesis, characterization and theoretical studies of three new chromium isoporphyrins are reported because a comprehensive study on chromium isoporphyrin is not known in the literature. On treatment with ammonium ceric nitrate as an oxidizing agent in a methanol medium chromium porphyrins easily form compounds which have strong absorbance at lower energy region (800 to 900 nm) which is the unique indication of isoporphyrin formation. Based on the standard spectroscopic (UV–Visible, Mass, PXRD and IR spectroscopy) analysis used for isoporphyrin characterization it is reasonable to conclude that the synthesized compounds are most probably methoxy chromium isoporphyrins, and accordingly named as chloro[5-(methoxy)-5,10,15,20-tetrakis-5,21H porphinato]chromium(III) nitrate,(<strong>1b</strong>), chloro[5-(methoxy)-5,10,15,20-tetrakis(4-methyl)- 5,21H-porphinato]chromium(III) nitrate,(<strong>2b</strong>), chloro[5-(methoxy)-5,10,15,20-tetrakis(4- methoxy)-5,21H-porphinato]chromium(III) nitrate, (<strong>3b</strong>). The parent compounds for the isoporphyrins are respectively [Cr^IIITPPCl] (<strong>1a</strong>), [Cr^III(4-MeTPP)Cl](<strong>2a</strong>) and [Cr^III(4- OMeTPP)Cl](<strong>3a</strong>). We have also performed theoretical studies at DFT levels, such as geometry optimization, energy calculation, simulation of UV–Vis spectra, NBO, and global reactivity indices to understand the distinctive properties of the chromium isoporphyrins for the first time. The theoretical UV-visible spectra and HOMO-LUMO energy gap supported experimental results. Moreover, Rietveld refinement showed that the experimental PXRD plots closely match the theoretical plots supporting that the experimental structures are similar to the theoretically optimized structures. Chromium isoporphyrins are found to have a lower HOMO-LUMO energy gap than their parent porphyrins, which accounts for their ease of reduction and the appearance of UV–Vis spectra at lower energy regions. Furthermore, we investigated the antioxidant properties of chromium methoxy isoporphyrins and compared them to their parent porphyrins and observed that complex <strong>3b</strong> (77 %) has the highest antioxidant activity.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141603"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195535","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 and corrosion inhibition of 1-(4-anisyl)-3-(4-(pyridin-4-ylmethyl)phenyl)carbamide on mild steel in 1M HCl: A comprehensive study from experimental, theoretical and microscopic modelling perspectives","authors":"Gopal Senthilkumar ,&nbsp;Arumugam Ramachandran ,&nbsp;Panneerselvam Anitha ,&nbsp;Solaiyappan Ayyappan ,&nbsp;Pitchai Marimuthu","doi":"10.1016/j.molstruc.2025.141589","DOIUrl":"10.1016/j.molstruc.2025.141589","url":null,"abstract":"<div><div>In the present study, a novel, cost-effective organic corrosion inhibitor, 1-(4-anisyl)-3-(4-(pyridin-4-ylmethyl)phenyl)carbamide (U–OCH₃), was synthesized and characterized by spectroscopic techniques. The corrosion inhibition properties of U–OCH₃ against mild steel (MS) in 1 M HCl medium were evaluated through weight loss measurements, electrochemical tests, surface analysis, and theoretical calculations. The experimental results demonstrated that 200 ppm of U–OCH₃ exhibits excellent corrosion inhibition, with a high inhibition efficiency of 98.62 % at 303 K, though its effectiveness decreases with increasing temperature. Kinetic and thermodynamic analyses suggested that U–OCH₃ inhibits corrosion through physisorption, with a mixed-type inhibitive action that adheres to Langmuir's adsorption isotherm. Surface analysis using Scanning Electron Microscopy (SEM), Energy Dispersive X-ray Analysis (EDX), Atomic Force Microscopy (AFM), and X-ray Photoelectron Spectroscopy (XPS) confirmed the formation of a thin inhibitor film, which adsorbs onto the steel surface via interactions with the heteroatoms (pyridine and phenyl rings) in U–OCH₃. Density Functional Theory (DFT) calculations revealed a strong correlation between the inhibitor's molecular structure and efficacy. Fukui index analysis identified specific attack sites on the metal surface. At the same time, Molecular Dynamics Simulations (MDS) provided insights into the interaction energies between the inhibitor and the steel surface, further validated by Radial Distribution Function (RDF) measurements. The study also assessed the self-diffusion coefficient, fractional free volume (FFV), and interactions between the inhibitor film and corrosive species, with experimental results aligning closely with theoretical predictions.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141589"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195633","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":"Multi-stimuli circular dichroism responses, UV-enhanced emission in solution and circularly polarized luminescence of a pair of chiral cuprous complexes","authors":"Yu-Jie Kong ,&nbsp;Wen-Xiang Chai ,&nbsp;Zhong-Xu Wang ,&nbsp;Jia-Qi Hong ,&nbsp;Li Song","doi":"10.1016/j.molstruc.2025.141613","DOIUrl":"10.1016/j.molstruc.2025.141613","url":null,"abstract":"<div><div>A pair of chiral cuprous complexes, R/S-[Cu₂(BINAP)₂(3-CN-Py)(CH₃CN)₂](PF₆)₂·2CH₂Cl₂ (BINAP = 1,1′-binaphthyl-2,2′-diphenyl phosphine, 3-CN-Py = 3-cyanopyridine) (abbreviated as R/S-Cu2), was synthesized. The crystal structures, circular dichroism (CD) and circularly polarized luminescence (CPL) spectra of R/S-Cu2 showed good mirror symmetry. Multi-stimuli CD responses of R/S-Cu2 in DMSO solution to water as poor solvent, ultraviolet irradiation time, H₂O₂ as well as temperature and corresponding mechanisms were discovered for the first time in the field of cuprous compounds. The solid state luminescence of R/S-Cu2 may be ascribed to (M + L)L'CT transition according to TD-DFT calculations. The emission of R-Cu2, taken as an example, in DMSO solution showed enhancement upon short time UV irradiation, which may be due to the removal of the luminescence quencher of oxygen. The CPL properties of R/S-Cu2 in solution before and after short time UV irradiation were investigated (<em>g</em>_lum = ±5.3 × 10⁻³). This work provides a new research strategy and opens up a prospect for the multiple applications of chiral cuprous materials.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141613"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195983","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 highly efficient and magnetically separable Fe3O4@CeO2 nanoparticles for the catalytic production of some substituted 1, 5-benzodiazepines as potential orthopedic agents","authors":"Xingyu Jiang ,&nbsp;Ning Ma ,&nbsp;Hongwei Liu ,&nbsp;Chunyan Zhang ,&nbsp;Pengfei Lv ,&nbsp;Juan Zhang","doi":"10.1016/j.molstruc.2025.141590","DOIUrl":"10.1016/j.molstruc.2025.141590","url":null,"abstract":"<div><div>1, 5-Benzodiazepines are significant compounds that are commonly used in orthopedics, primarily for their anxiolytic and muscle relaxant properties. Heterogeneous catalysis offers a promising approach for conducting eco-friendly and sustainable organic transformations. Benzodiazepines are important nitrogen-containing heterocyclic compounds with numerous biological activities. The use of Fe₃O₄@CeO₂ as a catalyst for the synthesis of some substituted 1, 5-benzodiazepines is innovative and efficient. Characterization techniques including FT-IR (Fourier transform infrared), XRD (X-ray diffraction), FE-SEM (field emission scanning electron microscopy), TEM (transmission electron microscopy), EDS (energy dispersive X-ray spectroscopy), DRS (diffuse reflectance specroscopy), XPS (X-ray photoelectron spectroscopy) and VSM (vibrating magnetometry) are used to identify the catalyst physicochemical structure. Some important experimental parameters such as reaction time, mole ratio of reagents, and temperature are evaluated to assess the optimum reaction condition. The best reaction condition includes 1 mmol of aryl aldehyde, dimedone, and 1, 2-phenylenediamine in the presence of 20 mg Fe₃O₄@CeO₂ catalyst in 10 mL ethanol for 90 min. Moreover, stability and reusability studies have confirmed acceptable results for the performed catalytic reaction in multiple runs, indicating its practical applicability.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141590"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195540","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 and spectroscopic analysis in GdVO4:RE3+ (RE=Sm, Eu) by solid state metathesis for optical applications","authors":"Gopal Warutkar ,&nbsp;Nilesh Ugemuge ,&nbsp;Esarat Ansari ,&nbsp;Ashvini Pusdekar ,&nbsp;Shruti Dhale ,&nbsp;Priya Tumram ,&nbsp;Shruti Patle ,&nbsp;S.V. Moharil","doi":"10.1016/j.molstruc.2025.141591","DOIUrl":"10.1016/j.molstruc.2025.141591","url":null,"abstract":"<div><div>Solid state metathesis was successfully used to synthesize pristine and Sm³⁺, Eu³⁺ doped GdVO₄ phosphor. Emission spectra could be interpreted on the basis of the known energy level structure. Observed lifetimes in the millisecond range are consistent with the forbidden nature of the transitions. The excitation could be achieved through the absorption by the host vanadate group. Results for the phosphors synthesized by the metathesis method are similar to those reported previously for the phosphors prepared by the conventional methods like solid state reaction. These results show that solid state metathesis can accomplish a simple, fast, economic route for producing vanadate based luminescent materials for various applications.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1332 ","pages":"Article 141591"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143332332","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 thermally stable Ce3+ activated green phosphor for illuminating and temperature sensing application","authors":"Wei Lv ,&nbsp;Yan Gao ,&nbsp;Qingguang Zeng ,&nbsp;Xinxin Han ,&nbsp;Tao Hu","doi":"10.1016/j.molstruc.2025.141618","DOIUrl":"10.1016/j.molstruc.2025.141618","url":null,"abstract":"<div><div>The discovery of efficient green phosphor is of great interest in wide range of applications in lighting, display, scintillator, and temperature sensing. Herein, an innovated Ce³⁺-substituted green-emitting gallate phosphor is presented. The green emission in CaYGaO₄:Ce³⁺ originates from Ce³⁺occupying at octahedrally coordinated Y³⁺ site rather than Ca²⁺site. This preferential substitution is identified by DFT-based formation energy calculations and supported by Rietveld refinement and photoluminescence spectra. The Ce³⁺ ion experiences a strong crystal field splitting on the 5d states, and ultimately shifts the emission into green spectra region with dual emission band at 508 and 588 nm (λ_ex = 460 nm). The phosphor exhibits excellent thermal quenching property, as its integrated photoluminescence intensity at 150 °C and 250 °C can retain 72.33 % and 54.11 % of that at room temperature, respectively, resulting from the reduced nonradiative losses. A prototype WLED fabricated by coating the green emitting CaYGaO₄:Ce³⁺phosphor and red emitting CaAlSiN₃:Eu²⁺ phosphor onto a blue LED chip yields a warm light with uniform light distribution. And also, by utilizing the fluorescent intensity ratio of the two emission bands as a temperate index, the promising application of the phosphor for remote temperature sensing is also demonstrated.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141618"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195359","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":"Microwave synthesis, X-ray analysis, in vitro and in silico evaluation of the antioxidant and anti-urease activities of novel acridines derived from β-enaminones","authors":"Yousra Ouafa Bouone ,&nbsp;Abdeslem Bouzina ,&nbsp;Abdelhak Djemel ,&nbsp;Farouk Benaceur ,&nbsp;Chawki Bensouici ,&nbsp;Malika Ibrahim-Ouali ,&nbsp;Nour-Eddine Aouf","doi":"10.1016/j.molstruc.2025.141609","DOIUrl":"10.1016/j.molstruc.2025.141609","url":null,"abstract":"<div><div>A series of 14 acridine derivatives was synthesized from the condensation of different β-enaminones and aromatic aldehydes, under microwave irradiation in catalyst-free conditions. The synthesis was favored for its rapidity, good yields, and environmental friendliness as it avoided the use of dangerous products and involved the employment of simple reactants and benign reaction conditions. The introduction of an <em>ortho</em> substituent in the aromatic aldehyde ring led to novel acridine-derived molecules containing hydroxyl groups. The structure of imino-acridine <strong>5d</strong> was fully determined using XRD method and confirmed the obtainment of both <em>E</em>-(<em>R</em>) and <em>E</em>-(<em>S</em>) isomers. <em>In vitro</em> studies were performed to evaluate the antioxidant capacity of the synthesized compounds as well as the anti-urease activity. The results showed that the novel hydroxylated compound <strong>5m</strong> was potent in the DPPH antioxidant test (IC₅₀ = 0.99 ± ¦0.13 µmol/mL) and gave an interesting activity against urease enzyme with an IC₅₀ of 0.03 ± ¦0.01 µmol/mL that is considered better than the standard molecule thiourea (IC₅₀ = 0.10 ± ¦0.004 µmol/mL). An <em>in silico</em> investigation that consisted of a molecular docking study and molecular dynamics simulation was completed to predict the binding mode of the novel hydroxylated compound <strong>5m</strong> towards active sites of both xanthine oxidase and urease enzymes as antioxidant and anti-urease targets, respectively. Furthermore, we employed DFT calculations to analyze the electronic and geometric properties of the optimal compound, <strong>5m</strong> The HOMO and LUMO band gap energies, as well as the molecular electrostatic potential surface, were deduced for the stable structure.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141609"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195525","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":"Two Zn-based metal-organic frameworks constructed with the mixed ligands for fluorescence detection of Cu2+ and Co2+","authors":"Xiaojing Mao ,&nbsp;Huachang Li ,&nbsp;Yehong Shi ,&nbsp;Jiemin Liu ,&nbsp;Lijun Kuai ,&nbsp;Jijun Liu ,&nbsp;Yan Han ,&nbsp;Yuexi Huang ,&nbsp;Haijiao Xie","doi":"10.1016/j.molstruc.2025.141608","DOIUrl":"10.1016/j.molstruc.2025.141608","url":null,"abstract":"<div><div>Two zinc-based metal-organic frameworks, namely [Zn(L₁)(Phen)H₂O]_n (<strong>1</strong>) and {[Zn(L₂)(Phen)]⋅(H₂O)}_n (<strong>2</strong>), were successfully constructed by mixed ligands strategy (HL₁=1,4-benzendicarboxylic acid, Phen=1,10-phenanthroline monohydrate, HL₂=5-hydroxyisophthalic acid), and characterized by X-ray single crystal diffraction, elemental analysis, powder X-ray diffraction (PXRD), etc. The X-ray single crystal diffraction demonstrate that both <strong>1</strong> and <strong>2</strong> show 1D chain structure. The orbital energies of <strong>1, 2</strong> and ligands have been investigated using the Density Functional Theory (DFT) calculations. The fluorescent sensing experimental revealed that both <strong>1</strong> and <strong>2</strong> exhibited excellent selectivity and sensitivity towards Cu²⁺ and Co²⁺ions over other metal ions, and the detection limit (LOD) of Cu²⁺ and Co²⁺ for <strong>1</strong> were 0.077 μM and 0.15 μM, and the LOD of Cu²⁺ and Co²⁺ for <strong>2</strong> were 0.81 μM and 0.48 μM, respectively. In addition, the fluorescence quenching mechanism of Cu²⁺and Co²⁺can be attributed to energy competitive absorption. Furthermore, in the real sample detection, the recoveries of Cu²⁺ and Co²⁺ were 92.6 - 109.1 % and 96.7 - 110.0 %, respectively. This work provided a reliable method for the quantitative detection of Cu²⁺ and Co²⁺ and was successfully applied in river water with satisfactory recovery and precision.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141608"},"PeriodicalIF":4.0,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195357","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 adamantane derivatives for enhanced EGFR inhibition in MCF-7 breast cancer cells","authors":"Pradeep M. Uppar ,&nbsp;Keshav Kumar Harish ,&nbsp;Narasimha M Beeraka ,&nbsp;Zhang Xi ,&nbsp;Chaithanya Somu ,&nbsp;Mahendra Madegowda ,&nbsp;Mamatha Shinduvalli Kempasiddegowda ,&nbsp;Sindhu M. Parameshwaraiah ,&nbsp;Peter E. Lobie ,&nbsp;Kanchugarakoppal S. Rangappa ,&nbsp;Vijay Pandey ,&nbsp;Basappa Basappa","doi":"10.1016/j.molstruc.2025.141554","DOIUrl":"10.1016/j.molstruc.2025.141554","url":null,"abstract":"<div><div>Epidermal growth factor receptor (EGFR) is a key target in breast cancer (BC) treatment due to its significant role in disease progression. This study aims to synthesize novel heterocyclic compounds by tailoring adamantane with pyrazoline followed by piperazines to target EGFR in breast cancer cells. Synthesis of the heterocyclic compounds was performed by Claisen–Schmidt reaction followed by cyclization and concludes with substitution by secondary amines. Structure of the lead compound 1-(3-((3r,5r,7r)-adamantan-1-yl)-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-(4-(2-nitrophenyl)piperazin-1-yl)ethenone (6c) is confirmed by HRMS, ¹H &amp; ¹³C NMR, IR and Single crystal XRD. <em>In silico</em> docking studies were performed to investigate the molecular interactions of the compound 3, 4 &amp; 6c with the EGFR binding site and to calculate their binding energies. Molecular dynamics simulations were conducted to explore stability of protein-ligand complex for compound 6c within the active site groove of <em>EGFR protein</em> in comparison with its precursors. Additionally, cytotoxic effects of these compounds against MCF-7 breast cancer cells were evaluated using IC-50 assays. Among the synthesized compounds, 6c exhibited significant cytotoxic effects against MCF-7 cells, with IC-50 values of 1.22 μM. Compound 6c had binding energy of -8.6 kcal/mol, indicating strong interactions within the EGFR binding site indicating their anti-breast cancer potential.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1331 ","pages":"Article 141554"},"PeriodicalIF":4.0,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143195537","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}