The aim of this study was a detailed examination of the synthesis of 3-methyleneisoindolinones comprising various functional groups. Methylmagnesuim bromide and PTSA was employed for the synthesis of these compounds. A wide range of 3-methyleneisoindolinones were afforded in good to excellent yields. On the other hand, 3-methyleneisoindolinones was also obtained by an efficient microwave method. The frame work of these derivatives was constructed from 2- acetylbenzoic acid and various primary amines via two-component reaction. The obtained compounds were characterized by 1H NMR, 13C-NMR and IR and elemental analysis.
{"title":"Synthesis and Characterization of 3-Methylene Isoindolinones by Two Synthetic Routes","authors":"Hamida Jelali , Lamjed Mansour , Jameel Al-Tamimi , Eric Deniau , Mathieu Sauthier , Naceur Hamdi","doi":"10.1080/10406638.2021.1971269","DOIUrl":"10.1080/10406638.2021.1971269","url":null,"abstract":"<div><div>The aim of this study was a detailed examination of the synthesis of 3-methyleneisoindolinones comprising various functional groups. Methylmagnesuim bromide and PTSA was employed for the synthesis of these compounds. A wide range of 3-methyleneisoindolinones were afforded in good to excellent yields. On the other hand, 3-methyleneisoindolinones was also obtained by an efficient microwave method. The frame work of these derivatives was constructed from 2- acetylbenzoic acid and various primary amines via two-component reaction. The obtained compounds were characterized by <sup>1</sup>H NMR, <sup>13</sup>C-NMR and IR and elemental analysis.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 1-13"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89098798","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-02Epub Date: 2023-03-09DOI: 10.1080/10406638.2023.2187849
Alshimaysawee Sadeq , Yaser Mohamed Hasan , Zainab Mohsen Najm , Mustafa M. Kadhim , Zuhair I. Al Mashhadani
Diaryl sulfides and selenides are ubiquitous chemical structures found in natural products, synthetic organic semiconductors, agricultural, and various biologically active molecules. Therefore, the development of novel and efficient catalytic systems for the preparation of diaryl sulfides and selenides is an important challenge in organic synthesis. In this paper, we wish to report the construction of a novel and efficient nanomagnetic copper nanocatalyst through the immobilization of Cu(OAc)2 on the surface of magnetic nanoparticles modified with Imine-Thiazole as ligand. The as-fabricated Fe3O4@SiO2-(Imine-Thiazole)-Cu(OAc)2 nanocomposite shown high catalytic activity in the C-Se (83%-98%) and C-S bond formation at 100 °C. To the best of our knowledge, this is the first report on the use of magnetically reusable copper nanocatalyst for the synthesis of diaryl selenides and sulfides via the reaction of triarylbismuthanes with elemental Se or S powder under aerobic conditions. Recycling experiments revealed that the copper nanocatalyst could be easily recovered by a simple magnetic separation and recycled at least eight times without deterioration in catalytic activity.
{"title":"A Novel and Efficient Magnetically Recoverable Copper Catalyst for Synthesis of Symmetrical Diaryl Selenides and Sulfides","authors":"Alshimaysawee Sadeq , Yaser Mohamed Hasan , Zainab Mohsen Najm , Mustafa M. Kadhim , Zuhair I. Al Mashhadani","doi":"10.1080/10406638.2023.2187849","DOIUrl":"10.1080/10406638.2023.2187849","url":null,"abstract":"<div><div>Diaryl sulfides and selenides are ubiquitous chemical structures found in natural products, synthetic organic semiconductors, agricultural, and various biologically active molecules. Therefore, the development of novel and efficient catalytic systems for the preparation of diaryl sulfides and selenides is an important challenge in organic synthesis. In this paper, we wish to report the construction of a novel and efficient nanomagnetic copper nanocatalyst through the immobilization of Cu(OAc)<sub>2</sub> on the surface of magnetic nanoparticles modified with Imine-Thiazole as ligand. The as-fabricated Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>-(Imine-Thiazole)-Cu(OAc)<sub>2</sub> nanocomposite shown high catalytic activity in the C-Se (83%-98%) and C-S bond formation at 100 °C. To the best of our knowledge, this is the first report on the use of magnetically reusable copper nanocatalyst for the synthesis of diaryl selenides and sulfides via the reaction of triarylbismuthanes with elemental Se or S powder under aerobic conditions. Recycling experiments revealed that the copper nanocatalyst could be easily recovered by a simple magnetic separation and recycled at least eight times without deterioration in catalytic activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 118-132"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88420598","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-02Epub Date: 2022-01-07DOI: 10.1080/10406638.2021.2019064
Naceur Hamdi , Aziza Mnasri , Ibrahim S. Al Nasr , Waleed S. Koko , Tariq A. Khan , Bernhard Biersack , Ismail Özdemir , Nevin Gürbüz
The interaction of N,N-disubstituted benzimidazolium salts 2a–e with Ag2O formed new silver-(N-heterocyclic carbene) complexes 3a–e. Structural characterization of silver-(N-heterocyclic carbene) complexes was conducted by using NMR, FT-IR and elemental analysis. Preliminary catalytic studies using all the silver complexes 3a–e were performed on three-component coupling reaction of a series of aldehydes with alkynes and amines was demonstrated. Most of these reactions led to formation of the expected propargylamines in good conversions using low amounts catalyst and obviating both the use of purified reagents as employ of a glovebox. Complexes 3a and 3c exhibited good catalytic activities under neat conditions. The silver complexes 3a–e showed luminescence properties in CH3CN at room temperature.
N，N-二取代苯并咪唑盐2a-e与Ag2O相互作用形成新的银-（N-杂环碳）配合物3a-e。采用NMR、FT-IR和元素分析等手段对银- n -杂环碳烯配合物进行了结构表征。用所有的银配合物3a-e对一系列醛与炔和胺的三组分偶联反应进行了初步的催化研究。大多数这些反应导致形成预期的丙胺在良好的转化使用少量催化剂和避免纯化试剂的使用，如使用手套箱。配合物3a和3c在整洁条件下表现出良好的催化活性。银配合物3a-e在CH3CN中表现出室温下的发光性质。
{"title":"Highly Efficient Single A3-Coupling (Aldehyde-Amine-Alkyne) Reaction Catalyzed by Air Stable Silver-(N-Heterocyclic Carbene) Complexes: Synthesis and Characterization","authors":"Naceur Hamdi , Aziza Mnasri , Ibrahim S. Al Nasr , Waleed S. Koko , Tariq A. Khan , Bernhard Biersack , Ismail Özdemir , Nevin Gürbüz","doi":"10.1080/10406638.2021.2019064","DOIUrl":"10.1080/10406638.2021.2019064","url":null,"abstract":"<div><div>The interaction of N,N-disubstituted benzimidazolium salts <strong>2a–e</strong> with Ag<sub>2</sub>O formed new silver-(N-heterocyclic carbene) complexes <strong>3a–e.</strong> Structural characterization of silver-(N-heterocyclic carbene) complexes was conducted by using NMR, FT-IR and elemental analysis. Preliminary catalytic studies using all the silver complexes <strong>3a–e</strong> were performed on three-component coupling reaction of a series of aldehydes with alkynes and amines was demonstrated. Most of these reactions led to formation of the expected propargylamines in good conversions using low amounts catalyst and obviating both the use of purified reagents as employ of a glovebox. Complexes <strong>3a</strong> and <strong>3c</strong> exhibited good catalytic activities under neat conditions. The silver complexes <strong>3a–e</strong> showed luminescence properties in CH<sub>3</sub>CN at room temperature.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 14-29"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145898129","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-02Epub Date: 2023-01-24DOI: 10.1080/10406638.2023.2167217
Saade Abdalkareem Jasim , Doaa B. Mohammed , Abduladheem Turki Jalil , Ghassan F. Smaisim , Karrar Shareef Mohsen , Shaymaa Abed Hussein , Mustafa-Saleh Shafik
Due to their magnetic separation and recycling characteristics, magnetic nanocatalysts are widely used in a wide variety of organic reactions. 1,2,3-Triazoles are heterocyclic compounds with broad applications in organic chemistry, including medicine, materials, and synthetic chemistry; a wide range of 1,2,3-triazoles exhibits many biological activities, including activity against fungal, viral, allergic, and microbial infections has been also reported in the literature. In this work, a magnetic Fe3O4@SiO2 nanocatalyst modified with pyridine-tetrazole ligand supported copper (II) acetate [MNPs-Py/Tet-Cu(OAc)2] was constructed and used to catalyze this one-pot three-component reaction of NH-1,2,3-triazoles. This nanocatalyst can act as an excellent catalyst for these three-component reactions. The [MNPs-Py/Tet-Cu(OAc)2] nanocatalyst, which demonstrated effective magnetization as 43 emu/g, can be easily separate from the reaction mixture and reused for 7 times while preserving their catalytic activity. Also the diameter of the nanoparticles is about 70–97 nm with spherical morphology.
{"title":"An Efficient and Attractive Synthetic Protocol for Three-component Preparation of NH-1,2,3-Triazoles Using a Novel Magnetically Recoverable Copper Catalyst","authors":"Saade Abdalkareem Jasim , Doaa B. Mohammed , Abduladheem Turki Jalil , Ghassan F. Smaisim , Karrar Shareef Mohsen , Shaymaa Abed Hussein , Mustafa-Saleh Shafik","doi":"10.1080/10406638.2023.2167217","DOIUrl":"10.1080/10406638.2023.2167217","url":null,"abstract":"<div><div>Due to their magnetic separation and recycling characteristics, magnetic nanocatalysts are widely used in a wide variety of organic reactions. 1,2,3-Triazoles are heterocyclic compounds with broad applications in organic chemistry, including medicine, materials, and synthetic chemistry; a wide range of 1,2,3-triazoles exhibits many biological activities, including activity against fungal, viral, allergic, and microbial infections has been also reported in the literature. In this work, a magnetic Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub> nanocatalyst modified with pyridine-tetrazole ligand supported copper (II) acetate [MNPs-Py/Tet-Cu(OAc)<sub>2</sub>] was constructed and used to catalyze this one-pot three-component reaction of NH-1,2,3-triazoles. This nanocatalyst can act as an excellent catalyst for these three-component reactions. The [MNPs-Py/Tet-Cu(OAc)<sub>2</sub>] nanocatalyst, which demonstrated effective magnetization as 43 emu/g, can be easily separate from the reaction mixture and reused for 7 times while preserving their catalytic activity. Also the diameter of the nanoparticles is about 70–97 nm with spherical morphology.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 97-117"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75129773","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2026-01-02Epub Date: 2022-09-05DOI: 10.1080/10406638.2022.2118331
M. Krishna Priya , D. Reuben Jonathan , S. Muthu , B.R. Sivasankaran , G. Usha
(2E)-2-(3-(benzyloxy)-4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one [BMBD] was synthesized to obtain a single crystal. Single crystal X-ray Diffraction (SXRD) studies revealed the 3 D structure and the crystallographic information. Density Functional Theory (DFT) at the B3LYP level with 6-311++(d,p) basis set has been used for theoretical computation on the chemical reactivity of the materials. A Hirshfeld surface analysis was done to study the non-covalent interactions like hydrogen bonds, short contacts, C–H…π and π…π stacking interactions. Synthesized compounds were characterized by FT-IR, 1H-NMR and 13C-NMR spectral techniques to classify proton and carbon environments and stretching/bending vibrational frequency assignments. MTT assay was performed on the material to measure the toxicity and anticancer activity against normal Vero and MCF-7 cell lines, respectively. Molecular docking involving the title compound and protein target (PDB ID: 1M17) was also carried out to study the anti-breast cancer activity, which for the compound is outstanding.
{"title":"Synthesis and Chemical Exploration of an Organic Exocyclic Chalcone Derivative for Its Therapeutic Proficiency against Breast Cancer","authors":"M. Krishna Priya , D. Reuben Jonathan , S. Muthu , B.R. Sivasankaran , G. Usha","doi":"10.1080/10406638.2022.2118331","DOIUrl":"10.1080/10406638.2022.2118331","url":null,"abstract":"<div><div>(2E)-2-(3-(benzyloxy)-4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one [BMBD] was synthesized to obtain a single crystal. Single crystal X-ray Diffraction (SXRD) studies revealed the 3 D structure and the crystallographic information. Density Functional Theory (DFT) at the B3LYP level with 6-311++(d,p) basis set has been used for theoretical computation on the chemical reactivity of the materials. A Hirshfeld surface analysis was done to study the non-covalent interactions like hydrogen bonds, short contacts, C–H…π and π…π stacking interactions. Synthesized compounds were characterized by FT-IR, <sup>1</sup>H-NMR and <sup>13</sup>C-NMR spectral techniques to classify proton and carbon environments and stretching/bending vibrational frequency assignments. MTT assay was performed on the material to measure the toxicity and anticancer activity against normal Vero and MCF-7 cell lines, respectively. Molecular docking involving the title compound and protein target (PDB ID: 1M17) was also carried out to study the anti-breast cancer activity, which for the compound is outstanding.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 53-71"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75878863","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this research, the preparation of new (methylsulfonyl)pyrano[3,2-c]quinolone, and pyrano[3,2-c]quinoline-3-carbonitrile derivatives using starting materials including 1-methylquinoline-2,4-dione, methylsulfonylacetonitrile or malononitrile, and aromatic aldehydes in the presence of [Triazolamine][Acetate] as ionic liquid catalyst were described. A simple and green method for the synthesis of novel organic compounds in H2O as solvent under reflux temperature conditions using a green and recyclable ionic liquid as catalyst is reported. The synthesis of diverse and new pyrano[3,2-c]quinoline derivatives, easy work-up procedure, high yields of products, short reaction times, use of green solvent, easy recovery and separation of the catalyst are the advantages of this protocol.
{"title":"Synthesis of New (Methylsulfonyl)Pyrano[3,2-c]Quinoline and Pyrano[3,2-c]Quinoline-3-Carbonitrile Derivatives Using [Triazolamine][Acetate] as a Basic Ionic Liquid Catalyst","authors":"Farhad Shirzaei (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Writing – original draft Writing – review & editing) , Hamid Reza Shaterian (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/10406638.2025.2563102","DOIUrl":"10.1080/10406638.2025.2563102","url":null,"abstract":"<div><div>In this research, the preparation of new (methylsulfonyl)pyrano[3,2-<em>c</em>]quinolone, and pyrano[3,2-<em>c</em>]quinoline-3-carbonitrile derivatives using starting materials including 1-methylquinoline-2,4-dione, methylsulfonylacetonitrile or malononitrile, and aromatic aldehydes in the presence of [Triazolamine][Acetate] as ionic liquid catalyst were described. A simple and green method for the synthesis of novel organic compounds in H<sub>2</sub>O as solvent under reflux temperature conditions using a green and recyclable ionic liquid as catalyst is reported. The synthesis of diverse and new pyrano[3,2-<em>c</em>]quinoline derivatives, easy work-up procedure, high yields of products, short reaction times, use of green solvent, easy recovery and separation of the catalyst are the advantages of this protocol.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 2152-2165"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645484","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Two significant worldwide health issues that call for the creation of new therapeutic medicines are oxidative stress and antibiotic resistance. Quinazolinone-1,2,4-triazole derivatives, which have a variety of pharmacological characteristics, may be able to help with these problems. As possible antibacterial and anticancer targets, this study sought to synthesized novel quinazoline-4(3H)-one derivatives containing an NH group at position 3 with 1,2,4-triazoles (7a–7k). The chemical structures of all compounds were characterized by NMR (1H/13C), IR and mass spectroscopy. Notably, derivatives 7d and 7e exhibited the greatest MIC values against S. epidermidis, while 7f was the best against S. aureus with MIC of 3.5 μg mL−1, two-fold efficacy more than that was recorded with moxifloxacin. All of the synthesized compounds showed promising anti-proliferative activity, with one compounds 7e having potent cytotoxic activity against MDA-MB-231 cell line (IC50 = 11.80 ± 1.2 μM) and active against MCF-7 (IC50 = 11.80 ± 1.2 μM respectively) in comparison to the reference DXN (IC50 = 9.48 ± 0.6 and 7.12 ± 2.0 μM, respectively). Molecular docking was performed using the protein structure of E. coli Topoisomerase IV, with the interacting effectively with key residues IleA:116, SerA:117, ArgA:93, GluA:46, ThrA:163, and GlyA:71, consistent with their antimicrobial activity. The chemical nature of these compounds was revealed by performing the density functional theory (DFT) calculation using hybrid B3LYP functional with 6-31 g(d) basis set. Additionally, these compounds exhibited promising physicochemical properties, paving the way for discovering new antimicrobial drugs.
{"title":"Design, Synthesis, Molecular Docking, ADME/Tox Predictions and DFT Study of Quinazolinone-1,2,4-Triazole Analogues as Promising Antimicrobial Agents","authors":"Areveli Srinivas (Data curation Methodology Validation) , Jaya Shree Anireddy (Supervision Writing – review & editing) , Bhoomandla Srinu (Formal analysis Resources Software) , Konda Santosh Kumar (Conceptualization Data curation Resources Validation) , Gajula Ramesh Kumar (Formal analysis Resources) , Ramya Gollamudi (Formal analysis Validation Visualization)","doi":"10.1080/10406638.2025.2551225","DOIUrl":"10.1080/10406638.2025.2551225","url":null,"abstract":"<div><div>Two significant worldwide health issues that call for the creation of new therapeutic medicines are oxidative stress and antibiotic resistance. Quinazolinone-1,2,4-triazole derivatives, which have a variety of pharmacological characteristics, may be able to help with these problems. As possible antibacterial and anticancer targets, this study sought to synthesized novel quinazoline-4(3H)-one derivatives containing an NH group at position 3 with 1,2,4-triazoles (<strong>7a–7k</strong>). The chemical structures of all compounds were characterized by NMR (<sup>1</sup>H/<sup>13</sup>C), IR and mass spectroscopy. Notably, derivatives <strong>7d</strong> and <strong>7e</strong> exhibited the greatest MIC values against <em>S. epidermidis</em>, while <strong>7f</strong> was the best against <em>S. aureus</em> with MIC of 3.5 μg mL<sup>−1</sup>, two-fold efficacy more than that was recorded with moxifloxacin. All of the synthesized compounds showed promising anti-proliferative activity, with one compounds <strong>7e</strong> having potent cytotoxic activity against MDA-MB-231 cell line (IC<sub>50</sub> = 11.80 ± 1.2 μM) and active against MCF-7 (IC<sub>50</sub> = 11.80 ± 1.2 μM respectively) in comparison to the reference DXN (IC<sub>50</sub> = 9.48 ± 0.6 and 7.12 ± 2.0 μM, respectively). Molecular docking was performed using the protein structure of <em>E. coli</em> Topoisomerase IV, with the interacting effectively with key residues IleA:116, SerA:117, ArgA:93, GluA:46, ThrA:163, and GlyA:71, consistent with their antimicrobial activity. The chemical nature of these compounds was revealed by performing the density functional theory (DFT) calculation using hybrid B3LYP functional with 6-31 g(d) basis set. Additionally, these compounds exhibited promising physicochemical properties, paving the way for discovering new antimicrobial drugs.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 2002-2021"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cancer is a serious health issue that has affected people of all ages and everywhere for a long time. In view of it a library of thiazole—tetrahydropyridine—pyridine derivatives synthesized evaluated for their in vitro anticancer activity against human breast adenocarcinoma (MCF-7) and human lung cancer (A-549) cell lines, using Doxorubicin as the standard reference. The compound 6k with -F and -CH3 substituents found to be more potent with IC50 value of 8.72 ± 0.88 µM and 8.54 ± 0.85 µM against MCF-7 and A-549 cells, respectively, compound 6c containing trifluoromethoxy group as substituent with IC50 value of 9.45 ± 1.02 µM (MCF-7) and 9.59 ± 1.08 µM (A-549), compound 6 g with trifluoromethyl and methyl substituents presented prominent activity with IC50 value of 11.19 ± 1.03 µM (MCF-7) and 11.34 ± 1.07 µM (A-549) and compound 6 m with trifluoromethyl group showed good activity with IC50 value of 14.54 ± 1.03 µM (MCF-7) and 14.35 ± 1.05 µM (A-549). The toxicity test against Hek-293 revealed that they are not harmful to normal cells. Molecular docking study of potent ligand 6k revealed their best dock score and promising binding interactions. Presented ADME prediction of all compounds.
{"title":"Design, Synthesis, Cytotoxicity, and Molecular Docking of New Thiazole Linked Tetrahydropyridine: Pyridine Hybrids","authors":"Ram Mohan Malothu (Data curation Visualization) , Gangadhar Thalari (Data curation Visualization)","doi":"10.1080/10406638.2025.2554200","DOIUrl":"10.1080/10406638.2025.2554200","url":null,"abstract":"<div><div>Cancer is a serious health issue that has affected people of all ages and everywhere for a long time. In view of it a library of thiazole—tetrahydropyridine—pyridine derivatives synthesized evaluated for their <em>in vitro</em> anticancer activity against human breast adenocarcinoma (MCF-7) and human lung cancer (A-549) cell lines, using <em>Doxorubicin</em> as the standard reference. The compound <strong>6k</strong> with -F and -CH<sub>3</sub> substituents found to be more potent with IC<sub>50</sub> value of <strong>8.72 ± 0.88 µM</strong> and <strong>8.54 ± 0.85 µM</strong> against MCF-7 and A-549 cells, respectively, compound <strong>6c</strong> containing trifluoromethoxy group as substituent with IC<sub>50</sub> value of <strong>9.45 ± 1.02 µM</strong> (MCF-7) and <strong>9.59 ± 1.08 µM</strong> (A-549), compound <strong>6 g</strong> with trifluoromethyl and methyl substituents presented prominent activity with IC<sub>50</sub> value of <strong>11.19 ± 1.03 µM</strong> (MCF-7) and <strong>11.34 ± 1.07 µM</strong> (A-549) and compound <strong>6 m</strong> with trifluoromethyl group showed good activity with IC<sub>50</sub> value of <strong>14.54 ± 1.03 µM</strong> (MCF-7) and <strong>14.35 ± 1.05 µM</strong> (A-549). The toxicity test against Hek-293 revealed that they are not harmful to normal cells. Molecular docking study of potent ligand <strong>6k</strong> revealed their best dock score and promising binding interactions. Presented ADME prediction of all compounds.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 1909-1922"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645483","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cancer and antibiotic resistance offer serious obstacles in drug discovery and design, which could be addressed by the synthesis of novel heterocyclic compounds with diverse combinations. In view of this a library of new molecular hybrids that contain indazole, pyrimidine, and 1,2,3-triazole heterocycles (6a-l) were synthesized and screened for their in vitro anticancer efficacy against MCF-7, PC-3, and HeLa cancer cell lines, with results compared to those of Doxorubicin. Two molecules with 2-chloro (6d) and 4-nitro (6 g) substituents presented potent activity against the PC-3 cell line, with IC50 values of 3.28 ± 0.07 µM and 3.25 ± 0.06 µM, respectively, with reference to Doxorubicin (IC50 = 3.79 ± 0.02 µM). Another molecule with 3-fluoro (6i) substituent displayed substantial action against the MCF-7 cell line, with an IC50 value of 3.26 ± 0.04 µM. The 4-nitro compound (6 g) exhibited the outstanding activity, with an IC50 value of 3.25 ± 0.07 µM against the HeLa cell line. A diverse selection of bacterial and fungal strains were employed to assess the antimicrobial potential of these compounds, and against the strains 6d, 6 g, 6h, 6i, and 6 l exhibited notably robust action. Molecular docking experiments were conducted to further investigate the binding interactions of these derivatives, compound 6 l scored highest binding affinity value of −10.4 kcal/mol.a The predicted pharmacokinetics of the molecules indicate favorable drug-likeness properties.
{"title":"Design, Synthesis, Anticancer and Antimicrobial Evaluation and In Silico Study of Indazole – Pyrimidine – 1,2,3-Triazole Hybrids","authors":"Sharada Etnoori (Investigation Methodology) , Vishnu Thumma (Conceptualization Software Visualization Writing – original draft) , Nagendra Babu Chilakala (Formal analysis) , Raju Barothu (Formal analysis) , Premalatha Kokku (Conceptualization Investigation Methodology Supervision Validation Writing – original draft Writing – review & editing)","doi":"10.1080/10406638.2025.2532069","DOIUrl":"10.1080/10406638.2025.2532069","url":null,"abstract":"<div><div>Cancer and antibiotic resistance offer serious obstacles in drug discovery and design, which could be addressed by the synthesis of novel heterocyclic compounds with diverse combinations. In view of this a library of new molecular hybrids that contain indazole, pyrimidine, and 1,2,3-triazole heterocycles (<strong>6a-l</strong>) were synthesized and screened for their <em>in vitro</em> anticancer efficacy against MCF-7, PC-3, and HeLa cancer cell lines, with results compared to those of Doxorubicin. Two molecules with 2-chloro (<strong>6d</strong>) and 4-nitro (<strong>6 g</strong>) substituents presented potent activity against the PC-3 cell line, with IC<sub>50</sub> values of <strong>3.28 ± 0.07 µM</strong> and <strong>3.25 ± 0.06 µM</strong>, respectively, with reference to Doxorubicin (IC<sub>50</sub> = <strong>3.79 ± 0.02 µM</strong>). Another molecule with 3-fluoro (<strong>6i</strong>) substituent displayed substantial action against the MCF-7 cell line, with an IC<sub>50</sub> value of <strong>3.26 ± 0.04 µM</strong>. The 4-nitro compound (<strong>6 g</strong>) exhibited the outstanding activity, with an IC<sub>50</sub> value of <strong>3.25 ± 0.07 µM</strong> against the HeLa cell line. A diverse selection of bacterial and fungal strains were employed to assess the antimicrobial potential of these compounds, and against the strains <strong>6d</strong>, <strong>6 g</strong>, <strong>6h</strong>, <strong>6i</strong>, and <strong>6 l</strong> exhibited notably robust action. Molecular docking experiments were conducted to further investigate the binding interactions of these derivatives, compound <strong>6 l</strong> scored highest binding affinity value of −10.4 kcal/mol.a The predicted pharmacokinetics of the molecules indicate favorable drug-likeness properties.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 1890-1908"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645927","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this study, new low-toxicity tetrazole-based Schiff bases and their Pt(II) complexes were synthesized. The cytotoxicity profiles of the ligands and their Pt(II) complexes were evaluated using the WST-1 proliferation assay in healthy (Human umbilical vein endothelial cells [HUVEC]) and cancerous (Human lung adenocarcinoma, A549, and Human cervical carcinoma [HeLa]) cell lines, with cisplatin used as a reference drug. While the ligands exhibited negligible cytotoxicity, the Pt(II) complexes demonstrated moderate cytotoxic effects, with [Pt(Tet-SalCl)] showing higher potency than [Pt(Tet-SalH)]. To investigate the mechanism of cytotoxicity, in vitro calf thymus DNA (Ct-DNA) interaction studies and in silico molecular docking analyses were conducted. As a preliminary toxicity profiling step, in silico LD50 predictions were performed, yielding values of 747.416 mg/kg for (Tet-SalH) and 940.3818 mg/kg for (Tet-SalCl), supporting the low-toxicity profile of the synthesized ligands. Overall, this work presents the synthesis, characterization, and cytotoxic evaluation of novel low-toxicity ligands and their Pt(II) complexes, which, while showing slightly different activity and DNA interaction profiles compared to cisplatin at equivalent concentrations, demonstrate comparable behavior and underscore their promising therapeutic potential.
{"title":"DNA Binding and Anticancer Activity of Tetrazole-Based Schiff Bases and Their Platinum (II) Complexes via In Vitro and In Silico Endpoints","authors":"Fatma Okuş (Conceptualization Data curation Investigation Software Writing – original draft) , Nurşen Sarı (Conceptualization Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Yaprak Dilber Simay Demir (Investigation Methodology) , Elvan Hasanoğlu Özkan (Investigation Methodology) , Fatma Ünal (Writing – review & editing) , Deniz Yüzbaşıoğlu (Project administration Supervision Writing – review & editing) , Gonca Çakmak (Conceptualization Formal analysis Investigation Methodology Supervision Writing – review & editing)","doi":"10.1080/10406638.2025.2564767","DOIUrl":"10.1080/10406638.2025.2564767","url":null,"abstract":"<div><div>In this study, new low-toxicity tetrazole-based Schiff bases and their Pt(II) complexes were synthesized. The cytotoxicity profiles of the ligands and their Pt(II) complexes were evaluated using the WST-1 proliferation assay in healthy (Human umbilical vein endothelial cells [HUVEC]) and cancerous (Human lung adenocarcinoma, A549, and Human cervical carcinoma [HeLa]) cell lines, with cisplatin used as a reference drug. While the ligands exhibited negligible cytotoxicity, the Pt(II) complexes demonstrated moderate cytotoxic effects, with [Pt(Tet-SalCl)] showing higher potency than [Pt(Tet-SalH)]. To investigate the mechanism of cytotoxicity, <em>in vitro calf thymus</em> DNA (<em>Ct</em>-DNA) interaction studies and <em>in silico</em> molecular docking analyses were conducted. As a preliminary toxicity profiling step, <em>in silico LD<sub>50</sub></em> predictions were performed, yielding values of 747.416 mg/kg for (Tet-SalH) and 940.3818 mg/kg for (Tet-SalCl), supporting the low-toxicity profile of the synthesized ligands. Overall, this work presents the synthesis, characterization, and cytotoxic evaluation of novel low-toxicity ligands and their Pt(II) complexes, which, while showing slightly different activity and DNA interaction profiles compared to cisplatin at equivalent concentrations, demonstrate comparable behavior and underscore their promising therapeutic potential.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 2022-2043"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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