In this research, novel derivatives of spiropyrrolo[3,4-b]pyridine derivatives were synthesized in high yields by using multicomponent reaction (MCR) of ninhydrin, ammonium acetate, ethyl 2,4-dioxo-4-arylbutanoates, primary amines, methyl propiolate, and triethyl amine (Et3N) in aqueous media. The antioxidant activity of new synthesized spiropyrrolo[3,4-b]pyridine derivatives is due to having OH group which was evaluated by two procedures. This employed procedure for preparation of spiropyrrolo[3,4-b]pyridine derivatives conveys benefits including reaction with low time, products with high yields, and easy separation of products using an easy procedure.
{"title":"Synthesis of New Spiropyrrolo[3,4-b]Pyridine Derivatives Employed Multicomponent Reactions","authors":"Nafiseh Tabarsa , Ramin Zafar Mehrabian , S. Zahra Sayyed Alangi , Zinatossadat Hossaini","doi":"10.1080/10406638.2023.2273882","DOIUrl":"10.1080/10406638.2023.2273882","url":null,"abstract":"<div><div>In this research, novel derivatives of spiropyrrolo[3,4-b]pyridine derivatives were synthesized in high yields by using multicomponent reaction (MCR) of ninhydrin, ammonium acetate, ethyl 2,4-dioxo-4-arylbutanoates, primary amines, methyl propiolate, and triethyl amine (Et<sub>3</sub>N) in aqueous media. The antioxidant activity of new synthesized spiropyrrolo[3,4-b]pyridine derivatives is due to having OH group which was evaluated by two procedures. This employed procedure for preparation of spiropyrrolo[3,4-b]pyridine derivatives conveys benefits including reaction with low time, products with high yields, and easy separation of products using an easy procedure.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 170-182"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138563274","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}
While the underlying causes of neurodegenerative diseases are varied, neuroinflammation is a common feature in most cases. Targeting neuroinflammation through anti-inflammatory strategies has emerged as a promising approach to prevent neurodegeneration. In addition, monoamine oxidase (MAO) inhibition has been suggested as an effective target in neurodegeneration. In this context, both cyclooxygenase (COX) and monoamine oxidase (MAO) inhibition have gained attention for their potential neuroprotective effects. In this study, novel hydrazone derivatives bearing benzoxazolinone structure were designed and synthesized as potential multifunctional MAO/COX inhibitors with antioxidant properties. Due to their structural and conformational flexibility, hydrazone compounds can form tautomers and isomers. Consequently, signals corresponding to these isomers have been detected in the 1H-NMR spectra of the synthesized compounds, prompting detailed spectral analyses (NOESY) to determine their isomeric ratios. In vitro biological activity tests have shown that most of the compounds exhibited significant COX inhibition and good antioxidant activity. MAO-B inhibitor capacity of the compounds is better than that of MAO-A. The cytotoxicity of all compounds in the series was negligible. Among the series, compounds 3g exhibited notable dual COX/MAO-B inhibition while 3c displayed potent MAO-B inhibition accompanied by antioxidant activity, highlighting their potential for further investigation.
{"title":"New Acyl Hydrazone Derivatives: Synthesis, Conformational Analysis by NMR Spectroscopy, and Enzyme Inhibitory and Antioxidant Activities in Alzheimer Disease","authors":"Hayrünnisa Taşci (Data curation Formal analysis Investigation Methodology Resources Software Supervision Validation Visualization Writing – original draft) , Begüm Nurpelin Sağlık (Methodology Resources Writing – original draft) , Şenel Teke Tuncel (Investigation Methodology Resources Validation Visualization Writing – original draft) , İpek Baysal (Methodology Resources) , Birsen Tozkoparan (Investigation Methodology Supervision) , İlknur Doğan (Investigation Methodology Resources Validation Visualization Writing – original draft) , Nesrin Gökhan Kelekçi (Investigation Methodology Supervision Writing – original draft)","doi":"10.1080/10406638.2025.2571572","DOIUrl":"10.1080/10406638.2025.2571572","url":null,"abstract":"<div><div>While the underlying causes of neurodegenerative diseases are varied, neuroinflammation is a common feature in most cases. Targeting neuroinflammation through anti-inflammatory strategies has emerged as a promising approach to prevent neurodegeneration. In addition, monoamine oxidase (MAO) inhibition has been suggested as an effective target in neurodegeneration. In this context, both cyclooxygenase (COX) and monoamine oxidase (MAO) inhibition have gained attention for their potential neuroprotective effects. In this study, novel hydrazone derivatives bearing benzoxazolinone structure were designed and synthesized as potential multifunctional MAO/COX inhibitors with antioxidant properties. Due to their structural and conformational flexibility, hydrazone compounds can form tautomers and isomers. Consequently, signals corresponding to these isomers have been detected in the <sup>1</sup>H-NMR spectra of the synthesized compounds, prompting detailed spectral analyses (NOESY) to determine their isomeric ratios. <em>In vitro</em> biological activity tests have shown that most of the compounds exhibited significant COX inhibition and good antioxidant activity. MAO-B inhibitor capacity of the compounds is better than that of MAO-A. The cytotoxicity of all compounds in the series was negligible. Among the series, compounds <strong>3g</strong> exhibited notable dual COX/MAO-B inhibition while <strong>3c</strong> displayed potent MAO-B inhibition accompanied by antioxidant activity, highlighting their potential for further investigation.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 235-257"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147388060","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, we invented a heterogeneous and efficient TiO2@SiO2@SCu nanocomposite in which the coating of the photocatalytically active TiO2 with SiO2 is stabilized by doping with S and Cu. It is characterized by applying transmission electron microscopy (HR-TEM), field emission SEM (FE-SEM), energy-dispersive X-ray spectroscopy (EDAX), fourier-transform infrared spectroscopy (FT-IR), and X-ray diffraction (XRD). The TiO2@SiO2@SCu nanocomposite is an environmentally friendly and cost-effective catalyst for the synthesis of 2-amino-4H-benzo[b]pyran through a three-component condensation of aromatic or aliphatic aldehyde, 1,3-dicarbonyl compound, and malononitrile; similarly, 1,8-dioxo-octahydroxanthenes are effectively prepared through a pseudo-three-component condensation of aromatic or aliphatic aldehydes and dimedone in ethanol under reflux conditions. Good yields, minimal catalyst loading, simple purification and work-up, excellent atom economy, and easy recovery and recycling are among the key advantages of this approach. Throughout five recycling cycles, isolated derivatives have been confirmed by FT-IR,1H NMR,13C NMR, and HRMS without compromising the product’s yield or quality.
{"title":"Heterogeneous TiO2@SiO2@SCu Nanocatalyst Synthesis, Characterization for Green Synthesis of Benzo[b]Pyran and Xanthenes","authors":"Sajid Pinjari (Data curation Methodology Writing – original draft) , Rahul Aher (Formal analysis Resources Validation) , Bhagwat Uphade (Software Writing – review & editing) , Anil Gadhave (Conceptualization Data curation Formal analysis Methodology Supervision Writing – review & editing)","doi":"10.1080/10406638.2025.2582834","DOIUrl":"10.1080/10406638.2025.2582834","url":null,"abstract":"<div><div>In this study, we invented a heterogeneous and efficient TiO<sub>2</sub>@SiO<sub>2</sub>@SCu nanocomposite in which the coating of the photocatalytically active TiO<sub>2</sub> with SiO<sub>2</sub> is stabilized by doping with S and Cu. It is characterized by applying transmission electron microscopy (HR-TEM), field emission SEM (FE-SEM), energy-dispersive X-ray spectroscopy (EDAX), fourier-transform infrared spectroscopy (FT-IR), and X-ray diffraction (XRD). The TiO<sub>2</sub>@SiO<sub>2</sub>@SCu nanocomposite is an environmentally friendly and cost-effective catalyst for the synthesis of 2-amino-4<em>H</em>-benzo[<em>b</em>]pyran through a three-component condensation of aromatic or aliphatic aldehyde, 1,3-dicarbonyl compound, and malononitrile; similarly, 1,8-dioxo-octahydroxanthenes are effectively prepared through a pseudo-three-component condensation of aromatic or aliphatic aldehydes and dimedone in ethanol under reflux conditions. Good yields, minimal catalyst loading, simple purification and work-up, excellent atom economy, and easy recovery and recycling are among the key advantages of this approach. Throughout five recycling cycles, isolated derivatives have been confirmed by FT-IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, and HRMS without compromising the product’s yield or quality.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 258-278"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147388094","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}
Parthenin (1) is the phytotoxin present in abundantly available Parthenium hysterophorus L., which is a highly invasive species in many countries. Various Heck analogues of parthenin were prepared by reaction with aryl halides. This method tolerates the wide functionalities present in the aryl iodides, including halides, methyl, trifluoromethyl, hydroxy, methoxy, cyano, carboxylic acid, nitro, and amino groups. Good yields (54–90%) were observed for all the Heck products (3a-3r) of parthenin. All the compounds were evaluated for drug-likeness, ADME attributes, and toxicity assessment, which revealed that only three derivatives (3e, 3f, and 3 l, containing -F, -Cl, and -CN functional groups, respectively, on the substituted aryl ring) met all standards, including Lipinski’s rule & toxicity evaluation. In contrast, the parent compound 1 satisfied only Lipinski’s rule. ADME and toxicity predictions were performed through ADMETlab 3.0 and ProTox, while molecular docking with receptor proteins was conducted using the CB-Dock 2 tool. Molecular docking studies of selected analogues, viz. 3e, 3f, and 3 l against top receptor proteins, namely AP-1 and Cox-2 (−7.4 to −9.9 kcal/mol), found comparable to the reference drug dexamethasone (−7.9 to −10 kcal/mol). Due to their strong binding affinity toward the targeted proteins, the synthesized analogues may serve as promising candidates for the development of anti-diabetic, anti-inflammatory, and antioxidant agents, as they showed noteworthy interaction with the key receptor proteins involved in these pathways.
{"title":"Synthesis of Parthenin Analogues via Palladium-Catalyzed Heck Coupling Reaction, Their Toxicity Analysis, and In Silico Molecular Docking Studies","authors":"Ekta Bala (Data curation Investigation Methodology Writing – original draft) , Sunita Sharma (Investigation Methodology) , Ankit Kachore (Methodology Software) , Rohit Sharma (Investigation Methodology) , Manju Bala (Investigation Methodology) , Varun Aggarwal (Data curation Formal analysis Software) , Hemant Singh (Formal analysis Resources Software) , Saima (Formal analysis Resources) , Rakesh Kumar (Formal analysis Visualization) , Praveen Kumar Verma (Writing – review & editing Supervision Validation Visualization Conceptualization) , Bikram Singh (Validation Visualization Conceptualization)","doi":"10.1080/10406638.2025.2611789","DOIUrl":"10.1080/10406638.2025.2611789","url":null,"abstract":"<div><div>Parthenin (<strong>1</strong>) is the phytotoxin present in abundantly available <em>Parthenium hysterophorus</em> L., which is a highly invasive species in many countries. Various Heck analogues of parthenin were prepared by reaction with aryl halides. This method tolerates the wide functionalities present in the aryl iodides, including halides, methyl, trifluoromethyl, hydroxy, methoxy, cyano, carboxylic acid, nitro, and amino groups. Good yields (54–90%) were observed for all the Heck products (<strong>3a-3r</strong>) of parthenin. All the compounds were evaluated for drug-likeness, ADME attributes, and toxicity assessment, which revealed that only three derivatives (<strong>3e</strong>, <strong>3f</strong>, and <strong>3 l</strong>, containing -F, -Cl, and -CN functional groups, respectively, on the substituted aryl ring) met all standards, including Lipinski’s rule & toxicity evaluation. In contrast, the parent compound <strong>1</strong> satisfied only Lipinski’s rule. ADME and toxicity predictions were performed through ADMETlab 3.0 and ProTox, while molecular docking with receptor proteins was conducted using the CB-Dock 2 tool. Molecular docking studies of selected analogues, <em>viz</em>. <strong>3e, 3f</strong>, and <strong>3 l</strong> against top receptor proteins, namely AP-1 and Cox-2 (−7.4 to −9.9 kcal/mol), found comparable to the reference drug dexamethasone (−7.9 to −10 kcal/mol). Due to their strong binding affinity toward the targeted proteins, the synthesized analogues may serve as promising candidates for the development of anti-diabetic, anti-inflammatory, and antioxidant agents, as they showed noteworthy interaction with the key receptor proteins involved in these pathways.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 218-234"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147388059","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 : 2026-02-07Epub Date: 2025-09-25DOI: 10.1080/10406638.2025.2562216
Bader A. Salameh (Conceptualization Data curation Investigation Methodology Project administration Resources Supervision Validation Writing – original draft Writing – review & editing) , Duaa Alashram (Data curation Formal analysis Investigation) , Wamidh H. Talib (Data curation Methodology Validation) , Amneh Shtaiwi (Software Validation) , Rawan W. Hadi (Data curation Methodology Validation) , Raed Al-Qawasmeh (Conceptualization Methodology Visualization)
A series of amino derivatives of coumarin-maleimide hybrid compounds was synthesized, beginning with 7-amino-4-methylcoumarin. This compound reacts with 2,3-dichloromaleic anhydride to produce the corresponding 3,4-dichloromaleimide. By substituting the chlorine atom with various secondary or aromatic amines, a collection of 3-amino-4-chloromaleimides was obtained. Nineteen coumarin-maleimide hybrid compounds were tested for cytotoxicity against three cancer cell lines a breast cancer cell line (T47D), a cervical cancer cell line (HeLa), and a lung cancer cell line (A549), in addition to a normal monkey kidney cell line (VERO). Among these compounds, compound 3t exhibited the highest activity against the breast cancer cells (T47D, IC50 = 5.5 µM), surpassing the positive control doxorubicin (IC50 = 7.36 µM), followed by compounds 3p, 3n, and 3r, all of which demonstrated good IC50 values. In contrast, compounds 3c, 3a, and 3p exhibited the greatest activity against the lung cancer cell line. Notably, all compounds showed no toxicity against the normal VERO cells. Molecular docking studies indicated that compound 3t has an excellent binding affinity for two proteins: the human estrogen receptor alpha (hER) and the progesterone receptor (PR).
{"title":"Coumarin-Maleimide Hybrids: Design, Synthesis, Cytotoxic Activities, and Molecular Docking","authors":"Bader A. Salameh (Conceptualization Data curation Investigation Methodology Project administration Resources Supervision Validation Writing – original draft Writing – review & editing) , Duaa Alashram (Data curation Formal analysis Investigation) , Wamidh H. Talib (Data curation Methodology Validation) , Amneh Shtaiwi (Software Validation) , Rawan W. Hadi (Data curation Methodology Validation) , Raed Al-Qawasmeh (Conceptualization Methodology Visualization)","doi":"10.1080/10406638.2025.2562216","DOIUrl":"10.1080/10406638.2025.2562216","url":null,"abstract":"<div><div>A series of amino derivatives of coumarin-maleimide hybrid compounds was synthesized, beginning with 7-amino-4-methylcoumarin. This compound reacts with 2,3-dichloromaleic anhydride to produce the corresponding 3,4-dichloromaleimide. By substituting the chlorine atom with various secondary or aromatic amines, a collection of 3-amino-4-chloromaleimides was obtained. Nineteen coumarin-maleimide hybrid compounds were tested for cytotoxicity against three cancer cell lines a breast cancer cell line (T47D), a cervical cancer cell line (HeLa), and a lung cancer cell line (A549), in addition to a normal monkey kidney cell line (VERO). Among these compounds, compound <strong>3t</strong> exhibited the highest activity against the breast cancer cells (T47D, IC50 = 5.5 µM), surpassing the positive control doxorubicin (IC50 = 7.36 µM), followed by compounds <strong>3p</strong>, <strong>3n</strong>, and <strong>3r</strong>, all of which demonstrated good IC50 values. In contrast, compounds <strong>3c</strong>, <strong>3a</strong>, and <strong>3p</strong> exhibited the greatest activity against the lung cancer cell line. Notably, all compounds showed no toxicity against the normal VERO cells. Molecular docking studies indicated that compound <strong>3t</strong> has an excellent binding affinity for two proteins: the human estrogen receptor alpha (hER) and the progesterone receptor (PR).</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 202-217"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147388061","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 the research work, a novel and recoverable nanomagnetic pallidum catalyst [Fe3O4-Bis(Py-Imine)-PdCl2] based on the immobilization of Pd on the surface of magnetic Fe3O4 nanoparticles modified with picolylamine as ligand was designed and fabricated. The structure of the as-fabricated Fe3O4-Bis(Py-Imine)-PdCl2 nanocatalyst was characterized by FT-IR spectroscopy, SEM, TEM, EDX, ICP-OES, TGA, VSM, XRD and EDX mapping techniques. The Fe3O4-Bis(Py-Imine)-PdCl2 nanocomposite demonstrated the high activity in the preparation of diaryl ketones through one-pot three-component Suzuki reactions of phenylboronic acids with aryl iodides and Mo(CO)6. The recycling of the Fe3O4-Bis(Py-Imine)-PdCl2 catalyst was examined in the coupling of phenylboronic acid with 4-methyl iodobenzene and Mo(CO)6; the results revealed that this catalyst could be reused for more than 6 consecutive runs without a loss of activity. This method offers several remarkable features, such as high yield of products, simplicity of separation of products from catalysts, performing reactions in green solvent and mild conditions, ability to recycle and reusing the catalyst without significant reduction in its catalytic activity.
在本研究中，以吡啶胺为配体修饰的磁性Fe3O4纳米颗粒为载体，将Pd固定在Fe3O4- bis (Py-Imine)-PdCl2上，设计并制备了一种新型可回收的纳米磁性球催化剂[Fe3O4- bis (Py-Imine)-PdCl2]。采用FT-IR、SEM、TEM、EDX、ICP-OES、TGA、VSM、XRD和EDX作图技术对制备的Fe3O4-Bis(Py-Imine)-PdCl2纳米催化剂的结构进行了表征。Fe3O4-Bis（py -亚胺）-PdCl2纳米复合材料通过苯基硼酸与芳基碘化物和Mo(CO)6的一锅三组分铃木反应制备二芳基酮具有较高的活性。考察了苯硼酸与4-甲基碘苯和Mo(CO)6偶联反应中Fe3O4-Bis(Py-Imine)-PdCl2催化剂的再循环；结果表明，该催化剂可以连续重复使用6次以上而不损失活性。该方法具有收率高、产品与催化剂分离简单、在绿色溶剂和温和条件下进行反应、催化剂可回收再利用而不显著降低其催化活性等特点。
{"title":"Fabrication of Fe3O4-Bis(Py-Imine)-PdCl2 Nanocomposite as a Highly Active Nanomagnetic Catalyst for Carbonylative Suzuki Reactions of Phenylboronic Acid with Aryl Iodides and Mo(CO)6","authors":"Sulieman Ibraheem Shelash Al-Hawary , Rahman S. Zabibah , Muataz S. Alhassan , Yasir Q. Almajidi , Reena Gupta , Dahlia N. Al-Saidi , Fatime Satar Sheri , Rosario Mireya Romero-Parra , Adnan Shafiq","doi":"10.1080/10406638.2023.2231597","DOIUrl":"10.1080/10406638.2023.2231597","url":null,"abstract":"<div><div>In the research work, a novel and recoverable nanomagnetic pallidum catalyst [Fe<sub>3</sub>O<sub>4</sub>-Bis(Py-Imine)-PdCl<sub>2]</sub> based on the immobilization of Pd on the surface of magnetic Fe<sub>3</sub>O<sub>4</sub> nanoparticles modified with picolylamine as ligand was designed and fabricated. The structure of the as-fabricated Fe<sub>3</sub>O<sub>4</sub>-Bis(Py-Imine)-PdCl<sub>2</sub> nanocatalyst was characterized by FT-IR spectroscopy, SEM, TEM, EDX, ICP-OES, TGA, VSM, XRD and EDX mapping techniques. The Fe<sub>3</sub>O<sub>4</sub>-Bis(Py-Imine)-PdCl<sub>2</sub> nanocomposite demonstrated the high activity in the preparation of diaryl ketones through one-pot three-component Suzuki reactions of phenylboronic acids with aryl iodides and Mo(CO)<sub>6.</sub> The recycling of the Fe<sub>3</sub>O<sub>4</sub>-Bis(Py-Imine)-PdCl<sub>2</sub> catalyst was examined in the coupling of phenylboronic acid with 4-methyl iodobenzene and Mo(CO)<sub>6</sub>; the results revealed that this catalyst could be reused for more than 6 consecutive runs without a loss of activity. This method offers several remarkable features, such as high yield of products, simplicity of separation of products from catalysts, performing reactions in green solvent and mild conditions, ability to recycle and reusing the catalyst without significant reduction in its catalytic activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 153-169"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88694608","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 : 2026-02-07Epub Date: 2025-09-16DOI: 10.1080/10406638.2025.2552424
Eman A. E. El-Helw (Conceptualization Data curation Investigation Methodology Visualization Writing – original draft Writing – review & editing) , Sayed K. Ramadan (Conceptualization Data curation Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , Sobhi M. Gomha (Software Supervision Validation Writing – review & editing) , Amira T. Ali (Conceptualization Investigation Methodology Writing – original draft Writing – review & editing)
Heterocyclic systems including benzoquinolines are targeted molecules in synthetic and medicinal chemistry because they represent an essential framework in many biologically active agents. Thus, some benzo[h]quinoline-based thiazolidinone, thiazole, and pyrimidinethione candidates were designed and synthesized through reactions of benzo[h]quinoline-thiosemicarbazone with diverse carbon-centered electrophiles. The purity of compounds obtained was also confirmed with HPLC analysis. The in vitro antiproliferative activity against HepG2 and MCF-7 cancer cell lines showed the most potency of thiazolidinone 4 (IC50 = 10.18 ± 1.5 & 8.22 ± 1.3 µM) and pyrimidinethione 9 (IC50 = 8.16 ± 1.4 & 9.23 ± 1.2 µM) compared to doxorubicin (IC50 = 4.52 ± 0.3 & 4.15 ± 0.1 µM), being capable of possible chelation with key nucleobases. In silico target prediction recognized kinase as a more probable target, and molecular docking simulation toward EGFR enzyme (breast cancer kinase, PDB ID: 3W32) offered the best docking score of thiazolidinone 4 (S-score = −7.6064 kcal/mol), exhibiting main binding to EGFR enzyme active pockets with a binding energy nearer to doxorubicin (reference, S-score = −7.7989 kcal/mol) and W32 (co-crystallized ligand, S-score = −7.9107 kcal/mol). This indicated strong bonding to key nucleobases and amino acids through H-bonding (between carbonyl oxygen and LYS 745, common with doxorubicin) and hydrophobic interactions (between benzene ring and VAL 726), which may reveal its potential action as an antiproliferative agent and EGFR inhibitor. Also, modeling pharmacokinetics offered their desirable drug-likeness and oral bioavailability. This work may aid in developing new potent antitumor agents.
{"title":"Synthesis and In Silico Evaluation of Thiazole, Thiazolidinone, and Pyrimidinethione Candidates Bearing A Benzo[h]Quinoline Scaffold as Potential Antiproliferative Agents","authors":"Eman A. E. El-Helw (Conceptualization Data curation Investigation Methodology Visualization Writing – original draft Writing – review & editing) , Sayed K. Ramadan (Conceptualization Data curation Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , Sobhi M. Gomha (Software Supervision Validation Writing – review & editing) , Amira T. Ali (Conceptualization Investigation Methodology Writing – original draft Writing – review & editing)","doi":"10.1080/10406638.2025.2552424","DOIUrl":"10.1080/10406638.2025.2552424","url":null,"abstract":"<div><div>Heterocyclic systems including benzoquinolines are targeted molecules in synthetic and medicinal chemistry because they represent an essential framework in many biologically active agents. Thus, some benzo[<em>h</em>]quinoline-based thiazolidinone, thiazole, and pyrimidinethione candidates were designed and synthesized through reactions of benzo[<em>h</em>]quinoline-thiosemicarbazone with diverse carbon-centered electrophiles. The purity of compounds obtained was also confirmed with HPLC analysis. The <em>in vitro</em> antiproliferative activity against HepG2 and MCF-7 cancer cell lines showed the most potency of thiazolidinone <strong>4</strong> (IC<sub>50</sub> = 10.18 ± 1.5 & 8.22 ± 1.3 µM) and pyrimidinethione <strong>9</strong> (IC<sub>50</sub> = 8.16 ± 1.4 & 9.23 ± 1.2 µM) compared to doxorubicin (IC<sub>50</sub> = 4.52 ± 0.3 & 4.15 ± 0.1 µM), being capable of possible chelation with key nucleobases. <em>In silico</em> target prediction recognized kinase as a more probable target, and molecular docking simulation toward EGFR enzyme (breast cancer kinase, PDB ID: 3W32) offered the best docking score of thiazolidinone <strong>4</strong> (S-score = −7.6064 kcal/mol), exhibiting main binding to EGFR enzyme active pockets with a binding energy nearer to doxorubicin (reference, S-score = −7.7989 kcal/mol) and W32 (co-crystallized ligand, S-score = −7.9107 kcal/mol). This indicated strong bonding to key nucleobases and amino acids through H-bonding (between carbonyl oxygen and LYS 745, common with doxorubicin) and hydrophobic interactions (between benzene ring and VAL 726), which may reveal its potential action as an antiproliferative agent and EGFR inhibitor. Also, modeling pharmacokinetics offered their desirable drug-likeness and oral bioavailability. This work may aid in developing new potent antitumor agents.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 2","pages":"Pages 183-201"},"PeriodicalIF":2.6,"publicationDate":"2026-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147388062","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: 2023-08-08DOI: 10.1080/10406638.2023.2212103
Azhar Kamel , Ali khalaf Hasan , Ali Hussein Demin Al-Khafaji , Wesam R. Kadhum , Rosario Mireya Romero-Parra , M. Abdulfadhil Gatea , Hesham S. Mustafa
In this research work, Fe3O4@DABA-PA-CuBr2 nanocomposite was fabricated by a simple and inexpensive method by immobilizing copper(II) bromide on the surface of magnetic nanoparticles modified with 3,4-diaminobenzoic acid and picolinic acid. Deep eutectic solvents or DESs are green and environmentally friendly solvents that are used as catalyst or solvent in many reactions. The utilization of Fe3O4@DABA-PA-CuBr2 nanocatalyst in ChCl–Urea at 100 °C presented an attractive, environmentally benign and highly efficient catalytic system for the preparation of a broad range of diaryl sulfones through one-pot three-component coupling of aryl iodides, aryl boronic acids, and DABSO (as SO2 source). It should be noted that the Fe3O4@DABA-PA-CuBr2 catalyst was used several times without significant reduction of the catalytic activity. VSM, TEM, and ICP-OES analysis of the reused Fe3O4@DABA-PA-CuBr2 catalyst after eight cycles revealed that that the structure, magnetic property, shape, and size of the particles did not change significantly.
{"title":"A Green and Efficient Approach for Preparation of Diaryl Sulfones: Fe3O4@DABA-PA-CuBr2 Nanocomposite Catalyzed One-Pot Three-Component Aryl Iodides, Aryl Boronic Acids, and DABSO (as SO2 Source)","authors":"Azhar Kamel , Ali khalaf Hasan , Ali Hussein Demin Al-Khafaji , Wesam R. Kadhum , Rosario Mireya Romero-Parra , M. Abdulfadhil Gatea , Hesham S. Mustafa","doi":"10.1080/10406638.2023.2212103","DOIUrl":"10.1080/10406638.2023.2212103","url":null,"abstract":"<div><div>In this research work, Fe<sub>3</sub>O<sub>4</sub>@DABA-PA-CuBr<sub>2</sub> nanocomposite was fabricated by a simple and inexpensive method by immobilizing copper(II) bromide on the surface of magnetic nanoparticles modified with 3,4-diaminobenzoic acid and picolinic acid. Deep eutectic solvents or DESs are green and environmentally friendly solvents that are used as catalyst or solvent in many reactions. The utilization of Fe<sub>3</sub>O<sub>4</sub>@DABA-PA-CuBr<sub>2</sub> nanocatalyst in ChCl–Urea at 100 °C presented an attractive, environmentally benign and highly efficient catalytic system for the preparation of a broad range of diaryl sulfones through one-pot three-component coupling of aryl iodides, aryl boronic acids, and DABSO (as SO<sub>2</sub> source). It should be noted that the Fe<sub>3</sub>O<sub>4</sub>@DABA-PA-CuBr<sub>2</sub> catalyst was used several times without significant reduction of the catalytic activity. VSM, TEM, and ICP-OES analysis of the reused Fe<sub>3</sub>O<sub>4</sub>@DABA-PA-CuBr<sub>2</sub> catalyst after eight cycles revealed that that the structure, magnetic property, shape, and size of the particles did not change significantly.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 133-151"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80715724","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: 2022-01-18DOI: 10.1080/10406638.2021.2023591
A. Mejri , L. Mansour , N. Hamdi
A range of N-substituted isoindolin-1-one-3-phosphonate compounds 4 under mild and solvent-free conditions was prepared. The synthesized compounds were screened for their antimicrobial activities against gram-positive bacterial strains (Micrococcus luteus, Listeria monocytogenes, Staphylococcus aureus and Bacillus cereus), a gram-negative bacterial strain (Salmonella typhimurium). The compounds 4a and 4 b were the most active against M. luteus bacteria with inhibition zones (IZ) of 35 and 24 mm, respectively, and 4a was the most active against L. monocytogenes ATCC 1911 with an IZ of 22 mm. Minimum inhibitory concentration (MIC) of the synthesized compounds 4 and the two standards tetracycline and fluconazole was assessed against the four indicator microorganisms: L. monocytogenes ATCC 1911, S. aureus ATCC 6538, S. typhimurium ATCC 14028 and C. albicans (ATCC 90028). The lowest MIC values were obtained for the compound 4d. Against C. albicans (ATCC 90028).
{"title":"Synthesis and Antimicrobial Activity of Some of Isoindolin-1-One-3-Phosphonates under Mild and Solvent-Free Conditions","authors":"A. Mejri , L. Mansour , N. Hamdi","doi":"10.1080/10406638.2021.2023591","DOIUrl":"10.1080/10406638.2021.2023591","url":null,"abstract":"<div><div>A range of N-substituted isoindolin-1-one-3-phosphonate compounds <strong>4</strong> under mild and solvent-free conditions was prepared. The synthesized compounds were screened for their antimicrobial activities against gram-positive bacterial strains (<em>Micrococcus luteus</em>, <em>Listeria monocytogenes</em>, <em>Staphylococcus aureus</em> and <em>Bacillus cereus</em>), a gram-negative bacterial strain (<em>Salmonella typhimurium</em>). The compounds <strong>4a</strong> and <strong>4 b</strong> were the most active against <em>M. luteus</em> bacteria with inhibition zones (IZ) of 35 and 24 mm, respectively, and 4a was the most active against <em>L. monocytogenes</em> ATCC 1911 with an IZ of 22 mm. Minimum inhibitory concentration (MIC) of the synthesized compounds <strong>4</strong> and the two standards tetracycline and fluconazole was assessed against the four indicator microorganisms: L. <em>monocytogenes</em> ATCC 1911, <em>S. aureus ATCC 6538, S. typhimurium</em> ATCC 14028 and <em>C. albicans (ATCC 90028)</em>. The lowest MIC values were obtained for the compound <strong>4d</strong>. Against C. albicans (ATCC 90028).</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"46 1","pages":"Pages 30-39"},"PeriodicalIF":2.6,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79076029","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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