Pub Date : 2025-08-09Epub Date: 2024-12-31DOI: 10.1080/10406638.2024.2446518
Samir Bondock , Nada Alabbad , Rehab H. Abd El-Aleam , Moaz M. Abdou
Cancer remains one of the leading causes of death worldwide, despite significant advances in treatment. Targeting tyrosine kinases, such as the epidermal growth factor receptor (EGFR), has become a promising approach for the development of anticancer agents. In this study, we designed and synthesized a series of triazole and pyrazole-based pyridine derivatives (7a–c, 10a–c, 11, 14a, and 14b) to target EGFR-TK. Bioisosteric modifications were incorporated into these compounds, based on key pharmacophoric features of established EGFR-TK inhibitors. The compounds were evaluated for cytotoxicity against a range of cancer cell lines, including MCF-7, HepG2, HCT116, and EA hy926. Notably, compounds 14a and 14b, which feature the pyrazolo[3,4-b]pyridine-5-carbonitrile nucleus, demonstrated significant anticancer activity with lower IC50 values across all tested cell lines. These compounds exhibited potent inhibitory effects, indicating their potential as effective EGFR-TK inhibitors. In silico studies, including ADME predictions, molecular docking, and molecular dynamics simulations, further supported their favorable pharmacokinetic profiles and strong binding interactions with EGFR-TK. Our findings suggest that these triazole and pyrazole-based pyridine derivatives could serve as promising candidates for the development of targeted anticancer therapies.
{"title":"Tandem Synthesis and Computational Insights into Triazole and Pyrazole-Based Pyridine Derivatives Targeting EGFR-TK in Cancer Therapy","authors":"Samir Bondock , Nada Alabbad , Rehab H. Abd El-Aleam , Moaz M. Abdou","doi":"10.1080/10406638.2024.2446518","DOIUrl":"10.1080/10406638.2024.2446518","url":null,"abstract":"<div><div>Cancer remains one of the leading causes of death worldwide, despite significant advances in treatment. Targeting tyrosine kinases, such as the epidermal growth factor receptor (EGFR), has become a promising approach for the development of anticancer agents. In this study, we designed and synthesized a series of triazole and pyrazole-based pyridine derivatives (<strong>7a–c, 10a–c, 11, 14a,</strong> and <strong>14b</strong>) to target EGFR-TK. Bioisosteric modifications were incorporated into these compounds, based on key pharmacophoric features of established EGFR-TK inhibitors. The compounds were evaluated for cytotoxicity against a range of cancer cell lines, including MCF-7, HepG2, HCT116, and EA hy926. Notably, compounds <strong>14a</strong> and <strong>14b</strong>, which feature the pyrazolo[3,4-b]pyridine-5-carbonitrile nucleus, demonstrated significant anticancer activity with lower IC<sub>50</sub> values across all tested cell lines. These compounds exhibited potent inhibitory effects, indicating their potential as effective EGFR-TK inhibitors. In silico studies, including ADME predictions, molecular docking, and molecular dynamics simulations, further supported their favorable pharmacokinetic profiles and strong binding interactions with EGFR-TK. Our findings suggest that these triazole and pyrazole-based pyridine derivatives could serve as promising candidates for the development of targeted anticancer therapies.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 7","pages":"Pages 1211-1234"},"PeriodicalIF":2.6,"publicationDate":"2025-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145046107","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 present study focuses on the adsorption efficiency of nanomagnetic Fe3O4@CQDs/Si(OEt)(CH2)3NH/CC/PEG-400 (Fe3O4@CQDs/NH/CC/PEG-400) as an adsorbent for Cu2+ and Zn2+ removal from the contaminated solutions through the adsorption technique. The effect of pH, contact time, and adsorbent dosage in the 45 ppm concentration of Cu2+ and Zn2+ solutions was also evaluated. By increasing the concentration at pH = 7 and the contact time of 120 min, the adsorption capacity increases so that the maximum adsorption capacity of Cu2+ and Zn2+ ions is 219.9 and 159.2 mg/g, respectively. Based on the correlation coefficient (R2), the Langmuir isotherm and the pseudo-second-order models were selected. The proposed mechanisms of adsorbent are the formation of complexes, interparticle diffusion, ion exchange interaction, and electrostatic interaction. The results show that adsorbent can be used in five cycles with 91% removal efficiency.
{"title":"Fe3O4 Nanoparticles Decorated with a Modified Carbon Quantum Dot Shell: Synthesis, Characterization and Its Evaluation as an Efficient Adsorbent for Cu(ii) and Zn(ii) Ions Adsorption","authors":"Tahereh Akbarpour , Ardeshir Khazaei , Mahsa Mohammadi , Negin Sarmasti","doi":"10.1080/10406638.2025.2453527","DOIUrl":"10.1080/10406638.2025.2453527","url":null,"abstract":"<div><div>The present study focuses on the adsorption efficiency of nanomagnetic Fe<sub>3</sub>O<sub>4</sub>@CQDs/Si(OEt)(CH<sub>2</sub>)<sub>3</sub>NH/CC/PEG-400 (Fe<sub>3</sub>O<sub>4</sub>@CQDs/NH/CC/PEG-400) as an adsorbent for Cu<sup>2+</sup> and Zn<sup>2+</sup> removal from the contaminated solutions through the adsorption technique. The effect of pH, contact time, and adsorbent dosage in the 45 ppm concentration of Cu<sup>2+</sup> and Zn<sup>2+</sup> solutions was also evaluated. By increasing the concentration at pH = 7 and the contact time of 120 min, the adsorption capacity increases so that the maximum adsorption capacity of Cu<sup>2+</sup> and Zn<sup>2+</sup> ions is 219.9 and 159.2 mg/g, respectively. Based on the correlation coefficient (R<sup>2</sup>), the Langmuir isotherm and the pseudo-second-order models were selected. The proposed mechanisms of adsorbent are the formation of complexes, interparticle diffusion, ion exchange interaction, and electrostatic interaction. The results show that adsorbent can be used in five cycles with 91% removal efficiency.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 7","pages":"Pages 1310-1332"},"PeriodicalIF":2.6,"publicationDate":"2025-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048267","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 : 2025-08-09Epub Date: 2024-12-27DOI: 10.1080/10406638.2024.2445151
Tliba Sourour , Fedaoui Dalila , Joana L. C. Sousa , Artur M. S. Silva , Liacha Messaoud
Several recent research studies have demonstrated that N-acylhydrazones are well known as privileged scaffolds frequently used in the discovery of new potential antiparasitic compounds. The investigation of literature revealed that the synthesis of N˗acylhydrazones bearing the 1,4˗benzothiazin˗3-one pharmacophore has not been described. Therefore, it was considered interesting to attempt the synthesis of new N˗acylhydrazone derivatives containing 1,4˗benzothiazine˗3˗one fragment, thus obtaining a series of novel (E)-N′-(substituted benzylidene)-2(3-oxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)acetohydrazides. Thus, the targeted compounds were successfully synthesized via an easy and general procedure. Hence, 2-aminothiophenol was reacted with maleic anhydride to produce the ester 3,4-dihydro-2-methoxycarbonylmethyl-3-oxo-2H-1,4-benzothiazine. The hydrazinolysis of the obtained ester-based benzothiazinon-3-one was also realized to give the corresponding benzothiazinonic acid hydrazide derivative as a precursor for the synthesis of the desired N˗acylhydrazones, by their condensation with various substituted benzaldehydes. In an attempt to explain the duplication of some peaks observed from the 1H and 13C˗NMR spectral analysis performed on the structures of all newly synthesized N˗acylhydrazones in DMSO˗d6; it was concluded that they exist as a mixture of syn˗E and anti˗E diastereoisomers with different isomeric yield ratio. Generally, the results obtained in this study indicate that these N˗acylhydrazones may be envisaged for supplementary structural investigations, and as potential biologically active compounds in diverse applications.
{"title":"Synthesis and Characterization of Novel Benzothiazinonic N-Acylhydrazone Derivatives","authors":"Tliba Sourour , Fedaoui Dalila , Joana L. C. Sousa , Artur M. S. Silva , Liacha Messaoud","doi":"10.1080/10406638.2024.2445151","DOIUrl":"10.1080/10406638.2024.2445151","url":null,"abstract":"<div><div>Several recent research studies have demonstrated that <em>N</em>-acylhydrazones are well known as privileged scaffolds frequently used in the discovery of new potential antiparasitic compounds. The investigation of literature revealed that the synthesis of <em>N</em>˗acylhydrazones bearing the 1,4˗benzothiazin˗3-one pharmacophore has not been described. Therefore, it was considered interesting to attempt the synthesis of new <em>N</em>˗acylhydrazone derivatives containing 1,4˗benzothiazine˗3˗one fragment, thus obtaining a series of novel (<em>E</em>)-<em>N</em>′-(substituted benzylidene)-2(3-oxo-2H-benzo[b][1,4]thiazin-4(3<em>H</em>)-yl)acetohydrazides. Thus, the targeted compounds were successfully synthesized via an easy and general procedure. Hence, 2-aminothiophenol was reacted with maleic anhydride to produce the ester 3,4-dihydro-2-methoxycarbonylmethyl-3-oxo-2<em>H</em>-1,4-benzothiazine. The hydrazinolysis of the obtained ester-based benzothiazinon-3-one was also realized to give the corresponding benzothiazinonic acid hydrazide derivative as a precursor for the synthesis of the desired <em>N</em>˗acylhydrazones, by their condensation with various substituted benzaldehydes. In an attempt to explain the duplication of some peaks observed from the <sup>1</sup>H and <sup>13</sup>C˗NMR spectral analysis performed on the structures of all newly synthesized <em>N</em>˗acylhydrazones in DMSO˗<em>d<sub>6</sub></em>; it was concluded that they exist as a mixture of <em>syn˗E</em> and <em>anti˗E</em> diastereoisomers with different isomeric yield ratio. Generally, the results obtained in this study indicate that these <em>N</em>˗acylhydrazones may be envisaged for supplementary structural investigations, and as potential biologically active compounds in diverse applications.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 7","pages":"Pages 1197-1210"},"PeriodicalIF":2.6,"publicationDate":"2025-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048284","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 : 2025-05-28Epub Date: 2024-10-25DOI: 10.1080/10406638.2024.2418411
Thoraya A. Farghaly , Mona H. Ibrahim , Hanadi Y. Medrasi , Shimaa A. Metwally , Magdi E. A. Zaki , Sami A. Al-Hussain , Zeinab A. Muhammad , Refaie M. Kassab
In this context, we designed and synthesized a series of hydrazonal and their related indeno[1,2-b]pyridin-5-one derivatives to investigate their antibacterial and anti-biofilm properties. Several of the synthesized compounds exhibited significant efficacy against all microorganism species tested. Most of the compounds demonstrated favorable results when tested against Gram-positive bacteria. The derivatives 4a, 4f, 6c, and 6f exhibit the highest antimicrobial efficacy, as indicated by their minimum inhibitory concentration (MIC) values ranging from 4 to 512 μg/mL. We conducted additional investigations on 4a, 6c, and 6f for the purpose of examining their synergy using Checkerboard assay. Compound 6c demonstrated a synergistic impact against methicillin-sensitive Staphylococcus aureus (MSSA) and Pseudomonas aeruginosa, while exhibiting moderate synergistic activity against methicillin-resistant Staphylococcus aureus (MRSA). In addition, the simultaneous use of gentamycin with compounds 4a and 6f demonstrates a synergistic impact in fighting against methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa, respectively. Three chosen compounds were evaluated for their antibiofilm efficacy. Application of 4a, 6c, and 6f effectively reduced the production of biofilms in MRSA, MSSA, and Pseudomonas aeruginosa, resulting in a significant decrease compared to the untreated samples. In addition, ADME and pharmacokinetic analyses were conducted for the three most potent derivatives, namely 4a, 6c, and 6f. Compounds 4a and 6c were subjected to docking in the LasR Quorum-Sensing Receptor, whereas compounds 6c and 6f were docked in the sortase enzyme.
{"title":"Synthesis, Antibacterial, Anti-Biofilm Properties, and Docking Study of Indeno[1,2-b]Pyridin-5-One Derivatives","authors":"Thoraya A. Farghaly , Mona H. Ibrahim , Hanadi Y. Medrasi , Shimaa A. Metwally , Magdi E. A. Zaki , Sami A. Al-Hussain , Zeinab A. Muhammad , Refaie M. Kassab","doi":"10.1080/10406638.2024.2418411","DOIUrl":"10.1080/10406638.2024.2418411","url":null,"abstract":"<div><div>In this context, we designed and synthesized a series of hydrazonal and their related indeno[1,2-b]pyridin-5-one derivatives to investigate their antibacterial and anti-biofilm properties. Several of the synthesized compounds exhibited significant efficacy against all microorganism species tested. Most of the compounds demonstrated favorable results when tested against Gram-positive bacteria. The derivatives <strong>4a</strong>, <strong>4f</strong>, <strong>6c</strong>, and <strong>6f</strong> exhibit the highest antimicrobial efficacy, as indicated by their minimum inhibitory concentration (MIC) values ranging from 4 to 512 μg/mL. We conducted additional investigations on <strong>4a</strong>, <strong>6c</strong>, and <strong>6f</strong> for the purpose of examining their synergy using Checkerboard assay. Compound <strong>6c</strong> demonstrated a synergistic impact against methicillin-sensitive <em>Staphylococcus aureus</em> (MSSA) and <em>Pseudomonas aeruginosa</em>, while exhibiting moderate synergistic activity against methicillin-resistant <em>Staphylococcus aureus</em> (MRSA). In addition, the simultaneous use of gentamycin with compounds <strong>4a</strong> and <strong>6f</strong> demonstrates a synergistic impact in fighting against methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) and <em>Pseudomonas aeruginosa</em>, respectively. Three chosen compounds were evaluated for their antibiofilm efficacy. Application of <strong>4a</strong>, <strong>6c</strong>, and <strong>6f</strong> effectively reduced the production of biofilms in MRSA, MSSA, and <em>Pseudomonas aeruginosa</em>, resulting in a significant decrease compared to the untreated samples. In addition, ADME and pharmacokinetic analyses were conducted for the three most potent derivatives, namely <strong>4a</strong>, <strong>6c</strong>, and <strong>6f</strong>. Compounds <strong>4a</strong> and <strong>6c</strong> were subjected to docking in the LasR Quorum-Sensing Receptor, whereas compounds <strong>6c</strong> and <strong>6f</strong> were docked in the sortase enzyme.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 863-883"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534404","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 : 2025-05-28Epub Date: 2024-10-22DOI: 10.1080/10406638.2024.2418408
Hind Yassmine Chennai , Salah Belaidi , Mebarka Ouassaf , Leena Sinha , Onkar Prasad , Goncagül Serdaroğlu , Samir Chtita
Casein kinase 2 (CK2) is an ubiquitous, essential, and highly pleiotropic protein kinase whose abnormally high constitutive activity is suspected to underlie its pathogenic potential in neoplasia and other diseases. Recently, there has been a notable increase in interest in the use of casein kinase 2 (CK2) inhibitors to improve the treatment of a specific form of cancer while minimizing the risk of undesirable side effects. Recently, using different virtual screening approaches, we have identified several novel CK2 inhibitors. In particular, we have discovered that the coumarin moiety can be considered an attractive CK2 inhibitor scaffold. In the present work, quantitative structure-activity relationship (QSAR) analysis has been employed to envisage the inhibitory effects of 32 coumarin derivatives on the CK2 protein. The most efficient model is found by using multiple linear regression (MLR). Its capability is considered by the external and internal validation values found (R2 = 0.884, Q2cv = 0.822, R2pred = 0.821, and R2p = 0.811), which aligned well with Tropsha and Golbraikh’s approach. The highest docking score founded for the newly designed coumarins is −7.50 kcal mol-1, which indicates that candidates can bind to the CK2 receptor with greater affinity. Based on the results of the ADMET properties and drug similarity analyses, a DFT investigation was conducted to confirm the stability of the newly explored compounds. It appears that the most stable complexes are those of compound with the highest binding affinity with a lower risk of toxicité.
{"title":"Computational Study of Coumarin Compounds as Potential Inhibitors of Casein Kinase 2: DFT, 2D-QSAR, ADMET and Molecular Docking Investigations","authors":"Hind Yassmine Chennai , Salah Belaidi , Mebarka Ouassaf , Leena Sinha , Onkar Prasad , Goncagül Serdaroğlu , Samir Chtita","doi":"10.1080/10406638.2024.2418408","DOIUrl":"10.1080/10406638.2024.2418408","url":null,"abstract":"<div><div>Casein kinase 2 (CK2) is an ubiquitous, essential, and highly pleiotropic protein kinase whose abnormally high constitutive activity is suspected to underlie its pathogenic potential in neoplasia and other diseases. Recently, there has been a notable increase in interest in the use of casein kinase 2 (CK2) inhibitors to improve the treatment of a specific form of cancer while minimizing the risk of undesirable side effects. Recently, using different virtual screening approaches, we have identified several novel CK2 inhibitors. In particular, we have discovered that the coumarin moiety can be considered an attractive CK2 inhibitor scaffold. In the present work, quantitative structure-activity relationship (QSAR) analysis has been employed to envisage the inhibitory effects of 32 coumarin derivatives on the CK2 protein. The most efficient model is found by using multiple linear regression (MLR). Its capability is considered by the external and internal validation values found (R<sup>2</sup> = 0.884, Q2cv = 0.822, R<sup>2</sup>pred = 0.821, and R<sup>2</sup>p = 0.811), which aligned well with Tropsha and Golbraikh’s approach. The highest docking score founded for the newly designed coumarins is −7.50 kcal mol-1, which indicates that candidates can bind to the CK2 receptor with greater affinity. Based on the results of the ADMET properties and drug similarity analyses, a DFT investigation was conducted to confirm the stability of the newly explored compounds. It appears that the most stable complexes are those of compound with the highest binding affinity with a lower risk of toxicité.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 843-862"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534400","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 : 2025-05-28Epub Date: 2024-10-25DOI: 10.1080/10406638.2024.2417715
Sara M. Emam , Samir M. El Rayes , Ibrahim A. I. Ali , Hamdy A. Soliman , Mohamed S. Nafie
Some novel β-Ala-phthalazine derivatives were synthesized from the parent methyl 3-(2-(4-benzyl-1-oxophthalazin-2(1H)-yl) acetamido)propanoate (1). Then, ester 1 underwent hydrazinolysis to produce the hydrazide 2-(4-benzyl-1-oxophthalazin-2(1H)-yl)-N-(3-hydrazineyl-3-oxo propyl) acetamide (2). Under the azide coupling technique, hydrazide 2 formed azide 3 which was further coupled with some amines and amino acid esters hydrochloride to produce the corresponding novel dipeptides 4a–h and 5a–d, respectively. Finally, hydrazide 2 was condensed and/or cyclized with some ketones and/or active methylene compounds resulting in the formation of various derivatives 6a-e. Compounds 2, 6c, and 6d demonstrated significant cytotoxicity, with IC50 values of 1.33, 0.41, and 0.38 μM compared to Sorafenib (IC50 = 2.93 μM). Compounds 6d exhibited potent VEGFR2 inhibition by 97.6% with an IC50 value of 21.9 μM compared to Sorafenib (94.7% and IC50 value of 30.1 μM). The 6d treatment significantly increased apoptotic activity by 23.6-fold, causing a halt in cell proliferation at the G2/M phase. Ultimately, it exhibited a strong affinity for the VEGFR2 protein, with a binding energy of −26.8 Kcal/mol, and it established binding contacts with the crucial amino acids involved in the interaction.
{"title":"Synthesis and Cytotoxicity of Novel β-Ala-Phthalazine-Based Derivatives as VEGFR2 Inhibitors and Apoptosis-Inducers Against Liver Cancer","authors":"Sara M. Emam , Samir M. El Rayes , Ibrahim A. I. Ali , Hamdy A. Soliman , Mohamed S. Nafie","doi":"10.1080/10406638.2024.2417715","DOIUrl":"10.1080/10406638.2024.2417715","url":null,"abstract":"<div><div>Some novel β-Ala-phthalazine derivatives were synthesized from the parent methyl 3-(2-(4-benzyl-1-oxophthalazin-2(1H)-yl) acetamido)propanoate <strong>(1)</strong>. Then, ester <strong>1</strong> underwent hydrazinolysis to produce the hydrazide 2-(4-benzyl-1-oxophthalazin-2(1<em>H</em>)-yl)-<em>N</em>-(3-hydrazineyl-3-oxo propyl) acetamide (<strong>2</strong>). Under the azide coupling technique, hydrazide <strong>2</strong> formed azide <strong>3</strong> which was further coupled with some amines and amino acid esters hydrochloride to produce the corresponding novel dipeptides <strong>4a–h</strong> and <strong>5a–d,</strong> respectively. Finally, hydrazide <strong>2</strong> was condensed and/or cyclized with some ketones and/or active methylene compounds resulting in the formation of various derivatives <strong>6a-e</strong>. Compounds <strong>2</strong>, <strong>6c</strong>, and <strong>6d</strong> demonstrated significant cytotoxicity, with IC<sub>50</sub> values of 1.33, 0.41, and 0.38 μM compared to Sorafenib (IC<sub>50</sub> = 2.93 μM). Compounds <strong>6d</strong> exhibited potent VEGFR2 inhibition by 97.6% with an IC<sub>50</sub> value of 21.9 μM compared to Sorafenib (94.7% and IC<sub>50</sub> value of 30.1 μM). The <strong>6d</strong> treatment significantly increased apoptotic activity by 23.6-fold, causing a halt in cell proliferation at the G2/M phase. Ultimately, it exhibited a strong affinity for the VEGFR2 protein, with a binding energy of −26.8 Kcal/mol, and it established binding contacts with the crucial amino acids involved in the interaction.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 771-792"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534402","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 compound 6-fluoro-4-hydroxyquinolin-2(1H)-one (1) was synthesized and reacted with diazotized 2, 4-dimethylaniline in a basic medium, yielding the hydrazone derivative (2) as a deep yellow crystalline compound. The structure of the purified product was confirmed through FT-IR, 1D and 2D NMR, and mass spectroscopic analyses. The results showed that the product exclusively adopts a hydrazone structure, existing as an equilibrium mixture of E and Z geometrical isomers in solution. DFT quantum calculations at the B3LYP/6-311++G (d, p) level indicated that the hydrazone form of compound (2) is more stable than the proposed azo structure, with the Z-hydrazone isomer having the lowest total energy. Additionally, UV-Vis spectroscopy studies of the E and Z isomers of hydrazone compound (2) in solvents of varying polarities showed that the E isomer is the predominant species in non-polar solvents.
{"title":"Synthesis, Characterization and Study of E/Z Isomerization in 3-(2-(2,4-Dimethylphenyl) Hydrazono)-6-Fluoroquinolin-(1H, 3H)-2, 4-Dione","authors":"Enayatollah Moradi Rufchahi , Fatemeh Ashouri Mirsadeghi","doi":"10.1080/10406638.2024.2421235","DOIUrl":"10.1080/10406638.2024.2421235","url":null,"abstract":"<div><div>The compound 6-fluoro-4-hydroxyquinolin-2(1<em>H</em>)-one (<strong>1</strong>) was synthesized and reacted with diazotized 2, 4-dimethylaniline in a basic medium, yielding the hydrazone derivative (<strong>2</strong>) as a deep yellow crystalline compound. The structure of the purified product was confirmed through FT-IR, 1D and 2D NMR, and mass spectroscopic analyses. The results showed that the product exclusively adopts a hydrazone structure, existing as an equilibrium mixture of E and Z geometrical isomers in solution. DFT quantum calculations at the B3LYP/6-311++G (d, p) level indicated that the hydrazone form of compound (<strong>2</strong>) is more stable than the proposed azo structure, with the Z-hydrazone isomer having the lowest total energy. Additionally, UV-Vis spectroscopy studies of the E and Z isomers of hydrazone compound (<strong>2</strong>) in solvents of varying polarities showed that the E isomer is the predominant species in non-polar solvents.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 884-897"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534407","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 : 2025-05-28Epub Date: 2024-11-14DOI: 10.1080/10406638.2024.2426632
Hossein Falahatkar , Hossein Nasr-Isfahani , Ali Keivanloo
Hybrid compounds are synthetic scaffolds of two or more pharmacophores that can be recognized as important reagents to increase the desired activity of biologically active compounds. This investigation develops an efficient and successful procedure for the synthesis of hybrid compounds based on 1,2,3-triazole scaffolds. Hybrid compounds include benzimidazole linked-1,2,3-triazole 9a-d and thiazolo[3,2-a] benzimidazole linked-1,2,3-triazoles 10a-d prepared from acetylenic benzimidazoles and substituted iodophenyl-1,2,3-triazoles with 75-90% yields, through Sonogashira coupling and heteroannulation. The reactions were carried out in DMF as the solvent and catalyzed by palladium(II) acetate/copper(I) iodide, in the presence of morpholine as an effective base at 70 °C. One-pot reaction conditions, high reaction yields, and simple reaction procedures are the advantages of this method.
{"title":"Efficient Synthesis of Hybrid Compounds from 1,2,3-Triazoles, Benzimidazole, and Thiazolo[3,2-a]Benzimidazole Through Palladium-Catalyzed Coupling-Heteroannulation Reactions","authors":"Hossein Falahatkar , Hossein Nasr-Isfahani , Ali Keivanloo","doi":"10.1080/10406638.2024.2426632","DOIUrl":"10.1080/10406638.2024.2426632","url":null,"abstract":"<div><div>Hybrid compounds are synthetic scaffolds of two or more pharmacophores that can be recognized as important reagents to increase the desired activity of biologically active compounds. This investigation develops an efficient and successful procedure for the synthesis of hybrid compounds based on 1,2,3-triazole scaffolds. Hybrid compounds include benzimidazole linked-1,2,3-triazole <strong>9a-d</strong> and thiazolo[3,2-a] benzimidazole linked-1,2,3-triazoles <strong>10a-d</strong> prepared from acetylenic benzimidazoles and substituted iodophenyl-1,2,3-triazoles with 75-90% yields, through Sonogashira coupling and heteroannulation. The reactions were carried out in DMF as the solvent and catalyzed by palladium(II) acetate/copper(I) iodide, in the presence of morpholine as an effective base at 70 °C. One-pot reaction conditions, high reaction yields, and simple reaction procedures are the advantages of this method.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 915-925"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534643","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 : 2025-05-28Epub Date: 2024-12-19DOI: 10.1080/10406638.2024.2427801
Little Joice S. , Maria Jesu Raja S.
The concept of Kekulé structure (chemically) and perfect matching (mathematically) in a molecular graph G are analogous. A matching M in a graph G is a collection of independent edges in G and is interpreted to be perfect if every single vertex of G is incident with one and only one edge in M. An anti-forcing set S of edges or covalent bonds of G is considered to be present if the removal of S leaves the graph G with a unique perfect matching or Kekulé structure. The anti-forcing set S with the minimal cardinality is referred to as the minimum anti-forcing set, and its cardinality can be expressed as af (G). The anti-forcing number of k-circumscribed peri-condensed benzenoid graphs and certain circum-peri-condensed sheets were investigated and determined in this manuscript.
{"title":"Anti-Forcing Number of Certain k-Circumscribed Peri-Condensed Benzenoid Graphs","authors":"Little Joice S. , Maria Jesu Raja S.","doi":"10.1080/10406638.2024.2427801","DOIUrl":"10.1080/10406638.2024.2427801","url":null,"abstract":"<div><div>The concept of Kekulé structure (chemically) and perfect matching (mathematically) in a molecular graph <em>G</em> are analogous. A matching <em>M</em> in a graph <em>G</em> is a collection of independent edges in <em>G</em> and is interpreted to be perfect if every single vertex of <em>G</em> is incident with one and only one edge in <em>M</em>. An anti-forcing set <em>S</em> of edges or covalent bonds of <em>G</em> is considered to be present if the removal of <em>S</em> leaves the graph <em>G</em> with a unique perfect matching or Kekulé structure. The anti-forcing set <em>S</em> with the minimal cardinality is referred to as the minimum anti-forcing set, and its cardinality can be expressed as <em>af</em> (<em>G</em>). The anti-forcing number of <em>k</em>-circumscribed peri-condensed benzenoid graphs and certain circum-peri-condensed sheets were investigated and determined in this manuscript.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 996-1009"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534401","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 : 2025-05-28Epub Date: 2024-11-21DOI: 10.1080/10406638.2024.2426631
Leila Zare Fekri , Mohaddeseh Kadivar-Kalmarzi , Rajender S. Varma
Azo dyes, comprising azo functionalities joined to aromatic sp2-hybridized C-atom or methane, are deployed in industry and can also be exploited as medicine due to their inherent biological activities. This importance renders the synthesis of these category of azo compounds significant and attractive. Herein, the recent synthesis of various derivatives of heterocyclic compounds with azo moiety such as oxazoles, benzoxazine, diindolylmethanes, coumarins, dihydropyridines, imidazoles, schiff bases, pyrazolopyridines, thiazolidines, thiophenes, pyrimido[4,5-e][1, 3, 4]thiadiazines, quinazolines, thiazoles, oxathiine and pyrazoles, are reviewed for the period 2011-2024. Some of azo dispersive dyes have been evaluated based on biological activity or solvatochromism effect which are also deliberated in this review.
{"title":"Heterocyclic Scaffolds Bearing –N=N- Moiety: Recent Advances in the Synthesis of Heterocyclic Azo-Dispersive Dyes","authors":"Leila Zare Fekri , Mohaddeseh Kadivar-Kalmarzi , Rajender S. Varma","doi":"10.1080/10406638.2024.2426631","DOIUrl":"10.1080/10406638.2024.2426631","url":null,"abstract":"<div><div>Azo dyes, comprising azo functionalities joined to aromatic sp2-hybridized C-atom or methane, are deployed in industry and can also be exploited as medicine due to their inherent biological activities. This importance renders the synthesis of these category of azo compounds significant and attractive. Herein, the recent synthesis of various derivatives of heterocyclic compounds with azo moiety such as oxazoles, benzoxazine, diindolylmethanes, coumarins, dihydropyridines, imidazoles, schiff bases, pyrazolopyridines, thiazolidines, thiophenes, pyrimido[4,5-e][1, 3, 4]thiadiazines, quinazolines, thiazoles, oxathiine and pyrazoles, are reviewed for the period 2011-2024. Some of azo dispersive dyes have been evaluated based on biological activity or solvatochromism effect which are also deliberated in this review.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 5","pages":"Pages 926-995"},"PeriodicalIF":2.4,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144534405","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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