A highly efficient and environmentally friendly synthetic strategy has been developed for the construction of novel bis(trifluoromethyl)phenyl-quinoline-benzamide-[1, 8]-naphthyridine and imidazo[1,2-a][1, 8]-naphthyridine derivatives. The structures of the synthesized compounds were confirmed by 1HNMR,13CNMR, and Mass data. The synthesized compounds (5/7a-e) were evaluated for their anticancer activity against three human cancer cell lines: MCF-7, A549, and SiHa. Among them, derivatives 5b and 5e displayed the most potent activity with IC50 values 11.25 ± 0.09 μM, 23.19 ± 0.45 μM, 29.22 ± 0.35 μM and 13.45 ± 0.09 μM, 26.24 ± 0.41 μM, 30.18 ± 0.39 μM. The synthesized derivatives were evaluated for their antimicrobial activity against pathogenic bacterial and fungal strains. All synthesized compounds demonstrated notable biological activity. Molecular docking studies were performed to evaluate the interactions of compounds 5/7a–e with selected target proteins. The results revealed strong binding affinities and favorable molecular interactions, supporting their potential as therapeutic agents. These derivatives exhibited significant antimicrobial and anticancer properties. Structure–activity relationship (SAR) analysis indicated that the presence of electron-withdrawing groups and hydrogen bond donors substantially enhanced cytotoxic effects.
{"title":"Synthesis, Biological Evaluation, and Molecular Docking Studies of [1, 8]-Naphthyridine Derivatives as Potential Anticancer and Antimicrobial Agents","authors":"Sontireddy Surender Reddy (Formal analysis Methodology Writing – original draft) , Kavati Shireesha (Validation) , Kumara Swamy Jella (Supervision)","doi":"10.1080/10406638.2025.2550361","DOIUrl":"10.1080/10406638.2025.2550361","url":null,"abstract":"<div><div>A highly efficient and environmentally friendly synthetic strategy has been developed for the construction of novel bis(trifluoromethyl)phenyl-quinoline-benzamide-[1, 8]-naphthyridine and imidazo[1,2-a][1, 8]-naphthyridine derivatives. The structures of the synthesized compounds were confirmed by <sup>1</sup>HNMR,<sup>13</sup>CNMR, and Mass data. The synthesized compounds (<strong>5/7a-e)</strong> were evaluated for their anticancer activity against three human cancer cell lines: MCF-7, A549, and SiHa. Among them, derivatives <strong>5b</strong> and <strong>5e</strong> displayed the most potent activity with IC<sub>50</sub> values 11.25 ± 0.09 μM, 23.19 ± 0.45 μM, 29.22 ± 0.35 μM and 13.45 ± 0.09 μM, 26.24 ± 0.41 μM, 30.18 ± 0.39 μM. The synthesized derivatives were evaluated for their antimicrobial activity against pathogenic bacterial and fungal strains. All synthesized compounds demonstrated notable biological activity. Molecular docking studies were performed to evaluate the interactions of compounds 5/7a–e with selected target proteins. The results revealed strong binding affinities and favorable molecular interactions, supporting their potential as therapeutic agents. These derivatives exhibited significant antimicrobial and anticancer properties. Structure–activity relationship (SAR) analysis indicated that the presence of electron-withdrawing groups and hydrogen bond donors substantially enhanced cytotoxic effects.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 1988-2001"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645928","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}
The development of targeted catalysts for environmental applications in the synthesis of biological compounds can be incredibly important. In the last few years, many catalysts have been reported that are potentially developable at the current time. In this research, Fe-based MOF as a bed and thiourea functionalities were constructed on it via a post-modification method. This method introduced the MOF(Fe)-TUR catalyst with hydrogen bonding ability, which selectively catalyzes the synthesis of new nicotinonitriles as well as chromeno[4,3-b]pyridine derivatives with good yields (70%–85%), suitable temperature (100 °C), easy purification and easy catalyst separation. The last step of the reaction process occurred via a cooperative vinylogous anomeric based oxidation. The structure of MOF(Fe)-TUR as a new H-bond catalyst was confirmed using several techniques such as FT-IR, XRD, XPS, SEM, EDX, Elemental mapping, BET, and BJH. The structure of the synthesized products was evaluated and confirmed by melting point, FT-IR, 1H-NMR, and 13C-NMR techniques. The novelty of this work lies in the development of a green and mild synthetic route and making MOF(Fe)-TUR as an environmentally friendly catalyst. Additionally, recycle and reusability of the presented catalyst are other advantages of the described methodology.
{"title":"Synthesis and Application of MOF(Fe)-TUR as a New H-Bond Catalyst for Synthesis of New Nicotinonitriles and Chromeno[4,3-b] Pyridines","authors":"Mahrokh Farrokh (Investigation Methodology Validation) , Hassan Sepehrmansourie (Investigation Writing – original draft) , Elham Tavakoli (Investigation Methodology Validation) , Mohammad Ali Zolfigol (Conceptualization Funding acquisition Project administration Resources Supervision Writing – review & editing) , Maryam Hajjami (Conceptualization Funding acquisition Project administration Resources Supervision Writing – review & editing)","doi":"10.1080/10406638.2025.2547604","DOIUrl":"10.1080/10406638.2025.2547604","url":null,"abstract":"<div><div>The development of targeted catalysts for environmental applications in the synthesis of biological compounds can be incredibly important. In the last few years, many catalysts have been reported that are potentially developable at the current time. In this research, Fe-based MOF as a bed and thiourea functionalities were constructed on it <em>via</em> a post-modification method. This method introduced the MOF(Fe)-TUR catalyst with hydrogen bonding ability, which selectively catalyzes the synthesis of new nicotinonitriles as well as chromeno[4,3-<em>b</em>]pyridine derivatives with good yields (70%–85%), suitable temperature (100 °C), easy purification and easy catalyst separation. The last step of the reaction process occurred <em>via</em> a cooperative vinylogous anomeric based oxidation. The structure of MOF(Fe)-TUR as a new H-bond catalyst was confirmed using several techniques such as FT-IR, XRD, XPS, SEM, EDX, Elemental mapping, BET, and BJH. The structure of the synthesized products was evaluated and confirmed by melting point, FT-IR, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR techniques. The novelty of this work lies in the development of a green and mild synthetic route and making MOF(Fe)-TUR as an environmentally friendly catalyst. Additionally, recycle and reusability of the presented catalyst are other advantages of the described methodology.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 1968-1987"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645926","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 : 2025-11-26DOI: 10.1080/10406638.2025.2531009
Ahmed M. El‑Saghier (Data curation Methodology Supervision) , Laila Abosella (Formal analysis Methodology) , Magda H. Abdellattif (Data curation Formal analysis Software) , Mohamed A. Gad (Formal analysis Writing – original draft Writing – review & editing)
The significant problems with the use of pesticides have made the use of safe substitutes essential. Consequently, families of new, ecologically safe norfloxacin series that are effective in killing insects were found using 5-substituted 1,2,4-thiadiazoles. If the thiadiazole ring were isosterically added to the norfloxacin ring, more potent biological activity and/or a greater variety of sap-feeding bugs were anticipated. The target synthesized compounds will undergo both modern elemental and characterization analyses (IR,1H NMR,13C NMR) to confirm their structure. The second category involved testing the generated chemicals on Aphis gossypii, the cotton aphid, nymphs, and adults. The most impacted synthetic chemical, compound 1, had an LC50 of 0.907 mg/L, according to the available information, whereas the LC50 of commercial thiacloprid was 0.255 mg/L. Molecular docking studies confirmed these findings, with compounds 1, 4, 7, and 10 displaying significantly stronger binding affinities to the hydrolase enzyme (−7.90, −7.70, −7.80, −7.70 kcal/mol) compared to the reference compound thiacloprid.
{"title":"Synthesis, Characterization, Insecticidal Activities, and in Silico Molecular Docking Study of Some New Norfloxacin Analogues Based on 5-Spiro-1,2,4-Thiadiazoles","authors":"Ahmed M. El‑Saghier (Data curation Methodology Supervision) , Laila Abosella (Formal analysis Methodology) , Magda H. Abdellattif (Data curation Formal analysis Software) , Mohamed A. Gad (Formal analysis Writing – original draft Writing – review & editing)","doi":"10.1080/10406638.2025.2531009","DOIUrl":"10.1080/10406638.2025.2531009","url":null,"abstract":"<div><div>The significant problems with the use of pesticides have made the use of safe substitutes essential. Consequently, families of new, ecologically safe norfloxacin series that are effective in killing insects were found using 5-substituted 1,2,4-thiadiazoles. If the thiadiazole ring were isosterically added to the norfloxacin ring, more potent biological activity and/or a greater variety of sap-feeding bugs were anticipated. The target synthesized compounds will undergo both modern elemental and characterization analyses (IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR) to confirm their structure. The second category involved testing the generated chemicals on <em>Aphis gossypii</em>, the cotton aphid, nymphs, and adults. The most impacted synthetic chemical, compound <strong>1</strong>, had an LC<sub>50</sub> of 0.907 mg/L, according to the available information, whereas the LC<sub>50</sub> of commercial thiacloprid was 0.255 mg/L. Molecular docking studies confirmed these findings, with compounds <strong>1</strong>, <strong>4</strong>, <strong>7</strong>, and <strong>10</strong> displaying significantly stronger binding affinities to the hydrolase enzyme (−7.90, −7.70, −7.80, −7.70 kcal/mol) compared to the reference compound thiacloprid.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 1923-1943"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645923","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 : 2025-11-26DOI: 10.1080/10406638.2025.2573682
Maha Salih Hussein (Conceptualization Investigation Methodology Project administration Resources Supervision Validation Writing – original draft Writing – review & editing) , Luay Ali Dhahi (Data curation Formal analysis Investigation Methodology Writing – original draft) , Hamid J. Mohammad (Data curation Formal analysis Investigation Methodology Writing – original draft) , Ghada F. Elmasry (Data curation Investigation Software Writing – original draft Writing – review & editing)
Over the past few decades, discovering new anticancer drugs was considered one of the biggest challenges for researchers. In this study, two series of acylhydrazones Z1-6 and hydrazones K1-6 were synthesized via reacting isoniazid or 2-hydrazinopyridine with some aromatic heterocyclic aldehydes under acidic conditions. The structures of all compounds were proven spectrophotometrically using proton nuclear magnetic resonance (1HNMR) and carbon-13 NMR (13CNMR), in addition to liquid chromatography-mass (LCMS) spectra, infrared (IR) spectra, and elemental analyses. Our compounds were evaluated for their anticancer activity against three types of cancer cells: colon HCT-116, lung A-549, and MCF-7 breast Adenocarcinoma cancer cells by the SRB method. Compounds Z3 and K4 showed the highest inhibition against colon cancer cells with IC50 values of 1.59 and <1 μM, respectively. Moreover, flowcytometric analysis revealed the ability of Z3 to cause cell cycle arrest at sub G1 phase and S phase in HCT-116 colon cancer cell line, in addition to prominent apoptotic effects. Subsequently, molecular docking was conducted to gain insight into the plausible mechanism of action for the most active compounds Z3 and K4 and it suggested Topoisomeras I as a potential biological target of the new counterparts. Absorption, Distribution, Metabolism Excretion, and Toxicity (ADMET) study predicted physicochemical and pharmacokinetic aspects. Furthermore, density functional theory (DFT) was carried out to better understand the structural properties, stability, and chemical reactivity of the most promising derivatives. In summary, this study offers new anticancer candidates with acylhyrazone/hydrazone scaffolds which may need further optimization.
{"title":"Unraveling the Anticancer Activity of Newly Synthesized Acylhydrazones and Hydrazones: In Vitro and Computational Insights","authors":"Maha Salih Hussein (Conceptualization Investigation Methodology Project administration Resources Supervision Validation Writing – original draft Writing – review & editing) , Luay Ali Dhahi (Data curation Formal analysis Investigation Methodology Writing – original draft) , Hamid J. Mohammad (Data curation Formal analysis Investigation Methodology Writing – original draft) , Ghada F. Elmasry (Data curation Investigation Software Writing – original draft Writing – review & editing)","doi":"10.1080/10406638.2025.2573682","DOIUrl":"10.1080/10406638.2025.2573682","url":null,"abstract":"<div><div>Over the past few decades, discovering new anticancer drugs was considered one of the biggest challenges for researchers. In this study, two series of acylhydrazones <strong>Z1-6</strong> and hydrazones <strong>K1-6</strong> were synthesized <em>via</em> reacting isoniazid or 2-hydrazinopyridine with some aromatic heterocyclic aldehydes under acidic conditions. The structures of all compounds were proven spectrophotometrically using proton nuclear magnetic resonance (<sup>1</sup>HNMR) and carbon-13 NMR (<sup>13</sup>CNMR), in addition to liquid chromatography-mass (LCMS) spectra, infrared (IR) spectra, and elemental analyses. Our compounds were evaluated for their anticancer activity against three types of cancer cells: colon HCT-116, lung A-549, and MCF-7 breast Adenocarcinoma cancer cells by the SRB method. Compounds <strong>Z3</strong> and <strong>K4</strong> showed the highest inhibition against colon cancer cells with IC<sub>50</sub> values of 1.59 and <1 μM, respectively. Moreover, flowcytometric analysis revealed the ability of <strong>Z3</strong> to cause cell cycle arrest at sub G1 phase and S phase in HCT-116 colon cancer cell line, in addition to prominent apoptotic effects. Subsequently, molecular docking was conducted to gain insight into the plausible mechanism of action for the most active compounds <strong>Z3</strong> and <strong>K4</strong> and it suggested Topoisomeras I as a potential biological target of the new counterparts. Absorption, Distribution, Metabolism Excretion, and Toxicity (ADMET) study predicted physicochemical and pharmacokinetic aspects. Furthermore, density functional theory (DFT) was carried out to better understand the structural properties, stability, and chemical reactivity of the most promising derivatives. In summary, this study offers new anticancer candidates with acylhyrazone/hydrazone scaffolds which may need further optimization.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 10","pages":"Pages 2044-2063"},"PeriodicalIF":2.6,"publicationDate":"2025-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145645931","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 : 2025-10-21DOI: 10.1080/10406638.2025.2509695
Rohit Kumar , Tahir Hussain Wani , Rashid Ali
In recent years, pyrrole and related compounds have engrossed a remarkable interest of the research community, as they have not only been a part of diverse natural and non-natural products but also played a vital role in molecular recognition, sensing, catalysis, and biological as well as material sciences, besides many more promising applications in other fields as well. In this minireview, we have for the first time disclosed the developments in the Piloty-Robinson pyrrole synthesis protocol, since its discovery in 1910 by O. Piloty and report in 1918 by G.M. Robinson and R. Robinson. Herein, we have tried to assemble all the reported pyrrole-based systems constructed by means of the Piloty-Robinson tactic. The authors believe that this specific and sole report for the preparation of substituted pyrroles via the Piloty-Robinson approach will provide a new avenue for the synthesis of a variety of valued pyrrole derivatives of specific interests.
{"title":"The Piloty-Robinson Reaction: A Versatile Tool for the Synthesis of 3,4-Disubstituted Pyrroles","authors":"Rohit Kumar , Tahir Hussain Wani , Rashid Ali","doi":"10.1080/10406638.2025.2509695","DOIUrl":"10.1080/10406638.2025.2509695","url":null,"abstract":"<div><div>In recent years, pyrrole and related compounds have engrossed a remarkable interest of the research community, as they have not only been a part of diverse natural and non-natural products but also played a vital role in molecular recognition, sensing, catalysis, and biological as well as material sciences, besides many more promising applications in other fields as well. In this minireview, we have for the first time disclosed the developments in the Piloty-Robinson pyrrole synthesis protocol, since its discovery in 1910 by O. Piloty and report in 1918 by G.M. Robinson and R. Robinson. Herein, we have tried to assemble all the reported pyrrole-based systems constructed by means of the Piloty-Robinson tactic. The authors believe that this specific and sole report for the preparation of substituted pyrroles via the Piloty-Robinson approach will provide a new avenue for the synthesis of a variety of valued pyrrole derivatives of specific interests.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1853-1873"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475872","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 : 2025-10-21DOI: 10.1080/10406638.2025.2508250
Shafieq Ahmad Wagay , Rashid Ali
A novel coumarin-based strapped calix[4]pyrrole, C4P9, was synthesized through an acid cyclization reaction followed by the reaction of coumarin with dipyrromethane. The structure of C4P9 was confirmed using 1H-NMR,13C-NMR, and mass spectrometry. Structural analysis revealed a pre-organized conformation for anion recognition, facilitated by intramolecular hydrogen bonding and the rigid strapping unit. An in-depth investigation of anion binding with various species such as F−, Br−, Cl−, I−, AcO−, NO3−, HSO4−, SCN−, and H2PO4− was conducted using UV-vis and NMR spectroscopy. The anion binding studies were validated by comparing 1H-NMR spectra of free receptor C4P9 with that of C4P9@F. The results from the online supramolecular Bindfit v0.5 program and Job’s plots indicated a 1:1 stoichiometry for the complexation between C4P9 and anions. The coumarin strap enhanced the binding ability and selectivity toward anions, as evidenced by calculations of binding constants. This was observed through interactions such as anion—π (involving aromatic moieties at the meso-position) and C–H—anion (involving the strapped linker and aromatic moiety) as well as N–H—anion interactions. This study demonstrates the potential of coumarin-based strapped calix[4]pyrrole as a versatile platform for developing functional anion receptors, particularly in anion/ion-pair coordination chemistry and supramolecular chemistry in general.
{"title":"Probing and Evaluating the Anion Binding Studies in Novel Coumarin Based Strapped Calix[4]Pyrrole","authors":"Shafieq Ahmad Wagay , Rashid Ali","doi":"10.1080/10406638.2025.2508250","DOIUrl":"10.1080/10406638.2025.2508250","url":null,"abstract":"<div><div>A novel coumarin-based strapped calix[4]pyrrole, C4P9, was synthesized through an acid cyclization reaction followed by the reaction of coumarin with dipyrromethane. The structure of <strong>C4P9</strong> was confirmed using <sup>1</sup>H-NMR,<sup>13</sup>C-NMR, and mass spectrometry. Structural analysis revealed a pre-organized conformation for anion recognition, facilitated by intramolecular hydrogen bonding and the rigid strapping unit. An in-depth investigation of anion binding with various species such as F<sup>−</sup>, Br<sup>−</sup>, Cl<sup>−</sup>, I<sup>−</sup>, AcO<sup>−</sup>, NO<sub>3</sub><sup>−</sup>, HSO<sub>4</sub><sup>−</sup>, SCN<sup>−</sup>, and H<sub>2</sub>PO<sub>4</sub><sup>−</sup> was conducted using UV-vis and NMR spectroscopy. The anion binding studies were validated by comparing <sup>1</sup>H-NMR spectra of free receptor <strong>C4P9</strong> with that of <strong>C4P9@F</strong>. The results from the online supramolecular Bindfit v0.5 program and Job’s plots indicated a 1:1 stoichiometry for the complexation between <strong>C4P9</strong> and anions. The coumarin strap enhanced the binding ability and selectivity toward anions, as evidenced by calculations of binding constants. This was observed through interactions such as anion—π (<em>involving aromatic moieties at the meso-position</em>) and C–H—anion (<em>involving the strapped linker and aromatic moiety</em>) as well as N–H—anion interactions. This study demonstrates the potential of coumarin-based strapped calix[4]pyrrole as a versatile platform for developing functional anion receptors, particularly in anion/ion-pair coordination chemistry and supramolecular chemistry in general.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1791-1806"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475880","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 a series of triazole linked vanillin derivatives were synthesized via Click chemistry and characterized using FTIR,1H NMR,1³C NMR, and HRMS/MS. Among the synthesized compounds, 6k, 6f, and 6b showed strong α-amylase inhibitory activity (IC50 = 50.70, 51.36, and 53.25 μg/mL, respectively) and α-glucosidase inhibitory activity (IC50 = 36.85, 37.99, and 38.49 μg/mL), comparable to acarbose (IC50 = 54.38 and 39.04 μg/mL). Compound 6e exhibited potent antibacterial activity (MIC = 0.5–2 μg/mL) against all tested strains, including S. aureus, S. pyogenes, S. typhi, and P. aeruginosa, comparable to streptomycin, while 6k also showed notable inhibition (MIC = 2–4 μg/mL). In antioxidant assays, 6a and 6j demonstrated IC50 values (48.25 and 49.31 μg/mL) comparable to ascorbic acid (IC50 = 49.18 μg/mL). Anti-inflammatory activity was significant for 6a and 6j (IC50 = 36.66 and 37.21 μg/mL), surpassing diclofenac (IC50 = 37.89 μg/mL). The compounds were nontoxic in cytotoxicity studies, with IC50 values >120 μg/mL for Vero cells, significantly higher than cisplatin (35.15 μg/mL). Molecular docking supported the in vitro results, with active compounds showing strong binding affinities, and SwissADME analysis indicated favorable pharmacokinetic properties. These findings highlight the multifunctional therapeutic potential of the designed compounds as anti-diabetic, antibacterial, antioxidant, and anti-inflammatory agents.
{"title":"A Click Chemistry Approach for the Synthesis of Triazole Linked Vanillin Scaffolds as Potent Pharmacophores: Anti-Diabetic, Anti-Inflammatory, Antioxidant, Molecular Docking and ADMET Investigations","authors":"Vardhaman Babagond , Kariyappa Katagi , Mahesh Akki , Vinuta Kamat , Delicia Avilla Barretto , Ashwini Jaggal , Surekha Kademani , Arunkumar Shirahatti","doi":"10.1080/10406638.2025.2507335","DOIUrl":"10.1080/10406638.2025.2507335","url":null,"abstract":"<div><div>In this study a series of triazole linked vanillin derivatives were synthesized via Click chemistry and characterized using FTIR,<sup>1</sup>H NMR,<sup>1</sup>³C NMR, and HRMS/MS. Among the synthesized compounds, <strong>6k, 6f,</strong> and <strong>6b</strong> showed strong α-amylase inhibitory activity (IC<sub>50</sub> = 50.70, 51.36, and 53.25 μg/mL, respectively) and α-glucosidase inhibitory activity (IC<sub>50</sub> = 36.85, 37.99, and 38.49 μg/mL), comparable to acarbose (IC<sub>50</sub> = 54.38 and 39.04 μg/mL). Compound <strong>6e</strong> exhibited potent antibacterial activity (MIC = 0.5–2 μg/mL) against all tested strains, including <em>S. aureus</em>, <em>S. pyogenes</em>, <em>S. typhi</em>, and <em>P. aeruginosa</em>, comparable to streptomycin, while <strong>6k</strong> also showed notable inhibition (MIC = 2–4 μg/mL). In antioxidant assays, <strong>6a</strong> and <strong>6j</strong> demonstrated IC<sub>50</sub> values (48.25 and 49.31 μg/mL) comparable to ascorbic acid (IC<sub>50</sub> = 49.18 μg/mL). Anti-inflammatory activity was significant for <strong>6a</strong> and <strong>6j</strong> (IC<sub>50</sub> = 36.66 and 37.21 μg/mL), surpassing diclofenac (IC<sub>50</sub> = 37.89 μg/mL). The compounds were nontoxic in cytotoxicity studies, with IC<sub>50</sub> values >120 μg/mL for Vero cells, significantly higher than cisplatin (35.15 μg/mL). Molecular docking supported the <em>in vitro</em> results, with active compounds showing strong binding affinities, and SwissADME analysis indicated favorable pharmacokinetic properties. These findings highlight the multifunctional therapeutic potential of the designed compounds as anti-diabetic, antibacterial, antioxidant, and anti-inflammatory agents.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1717-1740"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475873","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 : 2025-10-21DOI: 10.1080/10406638.2025.2563691
Ketan Vashisht (Data curation Formal analysis Writing – original draft) , Pooja Sethi (Data curation Formal analysis Investigation Writing – original draft) , Anshul Bansal (Data curation Formal analysis Investigation Writing – original draft) , Reena Kumari (Data curation Formal analysis Writing – original draft) , Manoj Singh (Data curation Formal analysis Investigation) , Ahmad Umar (Data curation Formal analysis Writing – review & editing) , Ahmed A. Ibrahim (Data curation Formal analysis Writing – review & editing) , Sotirios Baskoutas (Data curation Formal analysis Writing – review & editing)
A Series of newly designed pyrazole derivatives (3a–j) were synthesized through a condensation reaction between 3-(substituted phenylazo)-2,4-pentanedione (2) and 4-cyanophenyl hydrazine, yielding good results (70–85%). Their structural confirmations were carried out by using elemental analysis, mass spectrometry (MS), IR,1H NMR and 13C NMR spectroscopy. The pyrazole series 3a–j were screened for their cytotoxicity against the SH-SY5Y neuroblastoma cancer cell line. Compound 3j exhibited the lowest IC50 value of 19.18 µg/ml against the SH-SY5Y neuroblastoma cell line, demonstrating the highest effectiveness in inhibiting cell growth. Additionally, the compounds were evaluated for antibacterial activity against both Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas fluorescens and Escherichia coli). In addition, molecular docking analysis against 3V2B was performed, revealing that compound 3j exhibited a maximum binding affinity of −7.700 kcal/mol. The relative energies of compounds 3a–j were also determined through DFT studies utilizing the B3LYP methodology. This thorough analysis highlights the significant antibacterial and anticancer activities belonging to a new class of pyrazole derivatives, as well as their effective synthesis.
{"title":"Synthesis, Characterization, In Vitro Biological Evaluation, and Computational Studies of Pyrazole Derivatives as Promising Anticancer and Antibacterial Agents","authors":"Ketan Vashisht (Data curation Formal analysis Writing – original draft) , Pooja Sethi (Data curation Formal analysis Investigation Writing – original draft) , Anshul Bansal (Data curation Formal analysis Investigation Writing – original draft) , Reena Kumari (Data curation Formal analysis Writing – original draft) , Manoj Singh (Data curation Formal analysis Investigation) , Ahmad Umar (Data curation Formal analysis Writing – review & editing) , Ahmed A. Ibrahim (Data curation Formal analysis Writing – review & editing) , Sotirios Baskoutas (Data curation Formal analysis Writing – review & editing)","doi":"10.1080/10406638.2025.2563691","DOIUrl":"10.1080/10406638.2025.2563691","url":null,"abstract":"<div><div>A Series of newly designed pyrazole derivatives (<strong>3a–j</strong>) were synthesized through a condensation reaction between 3-(substituted phenylazo)-2,4-pentanedione <strong>(2)</strong> and 4-cyanophenyl hydrazine, yielding good results (70–85%). Their structural confirmations were carried out by using elemental analysis, mass spectrometry (MS), IR,<sup>1</sup>H NMR and <sup>13</sup>C NMR spectroscopy. The pyrazole series <strong>3a–j</strong> were screened for their cytotoxicity against the SH-SY5Y neuroblastoma cancer cell line. Compound <strong>3j</strong> exhibited the lowest IC<sub>50</sub> value of 19.18 µg/ml against the SH-SY5Y neuroblastoma cell line, demonstrating the highest effectiveness in inhibiting cell growth. Additionally, the compounds were evaluated for antibacterial activity against both Gram-positive bacteria (<em>Bacillus subtilis</em> and <em>Staphylococcus aureus</em>) and Gram-negative bacteria (<em>Pseudomonas fluorescens</em> and <em>Escherichia coli</em>). In addition, molecular docking analysis against 3V2B was performed, revealing that compound <strong>3j</strong> exhibited a maximum binding affinity of −7.700 kcal/mol. The relative energies of compounds <strong>3a–j</strong> were also determined through DFT studies utilizing the B3LYP methodology. This thorough analysis highlights the significant antibacterial and anticancer activities belonging to a new class of pyrazole derivatives, as well as their effective synthesis.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1741-1758"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475877","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 : 2025-10-21DOI: 10.1080/10406638.2025.2538877
Vadlamani Nagarjuna (Investigation) , Suresh Maddila (Supervision Writing – original draft) , Ravikumar Kapavarapu (Software) , Lalu Venigalla (Methodology) , Badampudi Santosh Kumar (Resources) , Amal F. Seliem (Writing – original draft) , Mohamed A. Nassan (Conceptualization) , Mahmoud M. Hessien (Writing – review & editing)
This study designed and synthesized novel phenoxyquinoline-pyrimidine hybrids (7a-k) as potential EGFR inhibitors, with 7a and 7k exhibiting superior cytotoxicity (IC50 = 2.13 ± 0.18 µM and 1.01 ± 0.10 µM against A549 and MCF-7 cancer cell lines, respectively) compared to Gefitinib. Molecular docking revealed strong binding to EGFR-TKD (−9.4 kcal/mol for 7a), supported by key interactions with MET793 and LEU844, while SAR analysis highlighted methoxy groups as critical for activity. These findings introduce a new class of hybrid anticancer agents with validated mechanistic insights, offering a foundation for targeted therapy development.
{"title":"A Novel Phenoxyquinoline-Pyrimidine Hybrids: Synthesis, In Silico ADME Studies, Molecular Docking and in Vitro Cytotoxic Activity","authors":"Vadlamani Nagarjuna (Investigation) , Suresh Maddila (Supervision Writing – original draft) , Ravikumar Kapavarapu (Software) , Lalu Venigalla (Methodology) , Badampudi Santosh Kumar (Resources) , Amal F. Seliem (Writing – original draft) , Mohamed A. Nassan (Conceptualization) , Mahmoud M. Hessien (Writing – review & editing)","doi":"10.1080/10406638.2025.2538877","DOIUrl":"10.1080/10406638.2025.2538877","url":null,"abstract":"<div><div>This study designed and synthesized novel phenoxyquinoline-pyrimidine hybrids (7a-k) as potential EGFR inhibitors, with <strong>7a</strong> and <strong>7k</strong> exhibiting superior cytotoxicity (IC<sub>50</sub> = 2.13 ± 0.18 µM and 1.01 ± 0.10 µM against A549 and MCF-7 cancer cell lines, respectively) compared to Gefitinib. Molecular docking revealed strong binding to EGFR-TKD (−9.4 kcal/mol for 7a), supported by key interactions with MET793 and LEU844, while SAR analysis highlighted methoxy groups as critical for activity. These findings introduce a new class of hybrid anticancer agents with validated mechanistic insights, offering a foundation for targeted therapy development.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1837-1852"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475875","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}
A simple, one-pot method for the synthesis of benzo[a][1,3]oxazino[6,5-c]phenazin-3-one derivatives has been reported via reactions of 4-hydroxy-1,2-naphthoquinone, benzene-1,2-diamine, methyl carbamate, and aromatic aldehydes in the presence of acetic acid as a catalyst under solvent-free conditions using microwave irradiation. Compared with other synthetic methods, this method has the advantages such as faster heating with higher energy efficiency, and less initial heating time, faster heating, higher energy efficiency, less space, more precise process control, mild reaction conditions, short reaction time, easy work-up, high yields of products, and selective heating can be mentioned.
{"title":"Green Synthesis of Novel Benzo[a][1,3]Oxazino[6,5-c]Phenazin-3-One Derivatives Under Solvent-Free Conditions Using Acetic Acid as an Efficient Catalyst via Microwave Irradiation","authors":"Bahareh Ghasemi Meimandi (Data curation Investigation Methodology) , Razieh Mohebat (Conceptualization Data curation Formal analysis Funding acquisition Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Alireza Hassanabadi (Writing – review & editing)","doi":"10.1080/10406638.2025.2556798","DOIUrl":"10.1080/10406638.2025.2556798","url":null,"abstract":"<div><div>A simple, one-pot method for the synthesis of benzo[<em>a</em>][1,3]oxazino[6,5-<em>c</em>]phenazin-3-one derivatives has been reported <em>via</em> reactions of 4-hydroxy-1,2-naphthoquinone, benzene-1,2-diamine, methyl carbamate, and aromatic aldehydes in the presence of acetic acid as a catalyst under solvent-free conditions using microwave irradiation. Compared with other synthetic methods, this method has the advantages such as faster heating with higher energy efficiency, and less initial heating time, faster heating, higher energy efficiency, less space, more precise process control, mild reaction conditions, short reaction time, easy work-up, high yields of products, and selective heating can be mentioned.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 9","pages":"Pages 1649-1655"},"PeriodicalIF":2.6,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475871","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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