Pub Date : 2025-01-02DOI: 10.1080/10406638.2024.2393249
Hani Hamidi , Masoumeh Hosseinzadeh , Daryoush Zareyee , Mohammad A. Khalilzadeh
Litsea costalis is a well-known medicinal plant in tropical and subtropical areas. Four significant flavonoids were extracted and characterized from the plant leaf extract. One component was discovered for the first time in flavonoid chemistry, flavan-4-ol, (3′, 4′-methylenedioxy-5,7-dimethoxy chroman-4-ol). Three flavonoids were discovered for the first time in this plant. The detected products are (+)-pinostrobin, (+)-onysilin, and (+)-pinocembrin. The fourth component was characterized for the first time in this plant and introduced in flavonoid chemistry. The extracted component antioxidant activity against DPPH indicated an IC50 value of around 30 µg/mL.
{"title":"Structural Elucidation of Some Flavonoids Isolated from Litsea costalis and Their Biological Evaluation","authors":"Hani Hamidi , Masoumeh Hosseinzadeh , Daryoush Zareyee , Mohammad A. Khalilzadeh","doi":"10.1080/10406638.2024.2393249","DOIUrl":"10.1080/10406638.2024.2393249","url":null,"abstract":"<div><div><em>Litsea costalis</em> is a well-known medicinal plant in tropical and subtropical areas. Four significant flavonoids were extracted and characterized from the plant leaf extract. One component was discovered for the first time in flavonoid chemistry, flavan-4-ol, (3′, 4′-methylenedioxy-5,7-dimethoxy chroman-4-ol). Three flavonoids were discovered for the first time in this plant. The detected products are (+)-pinostrobin, (+)-onysilin, and (+)-pinocembrin. The fourth component was characterized for the first time in this plant and introduced in flavonoid chemistry. The extracted component antioxidant activity against DPPH indicated an IC<sub>50</sub> value of around 30 µg/mL.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 98-105"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142204210","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 work describes a greener method of preparation of Fe3O4 nanoparticles, which are then functionalized to Fe3O4@SiO2@SO3H, and employed in the one-pot three-component synthesis of tetrahydrobenzo[b]pyran and dihydropyrano[3,2-c]chromene derivatives. These synthesized derivatives are an important class of heterocyclic scaffolds and exhibit significant potential as anti-coagulant, diuretic, spasmolytic, anticancer, and anti-anaphylactic agents. The prepared MNP-based catalysts were characterized using XRD, FE-SEM, VSM, TG-DTA, and Raman spectroscopy. The synthesis of derivatives involved the condensation reaction of enolizable compounds with aldehyde, dimedone, and ethyl cyanoacetate for tetrahydrobenzo[b]pyran, and the reaction of aromatic aldehyde, 4-hydroxycoumarin, and malononitrile for dihydropyrano[3,2-c]chromene synthesis. The reaction was optimized using different techniques such as stirring, ultrasonication, and microwave irradiation, with microwave irradiation method demonstrating faster product separation and high yield. The homogeneity of the isolated product was analyzed by FT-IR,1H-13C-NMR, and mass spectrometry. The advantages of this method include its simplicity, eco-friendliness, cost-effectiveness, and it also evades the use of toxic metals and solvents. The product is easily isolated through a simple workup process and recrystallization using ethanol yields pure product isolation.
{"title":"Eco-Friendly One-Pot Synthesis of Tetrahydrobenzo[b]Pyran and Dihydropyrano[3,2-c]Chromene Derivatives Using Functionalized Fe3O4@SiO2@SO3H Under MWI","authors":"Raju Shekhanavar , Santosh Khatavi , Kantharaju Kamanna","doi":"10.1080/10406638.2024.2389939","DOIUrl":"10.1080/10406638.2024.2389939","url":null,"abstract":"<div><div>The present work describes a greener method of preparation of Fe<sub>3</sub>O<sub>4</sub> nanoparticles, which are then functionalized to Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>@SO<sub>3</sub>H, and employed in the one-pot three-component synthesis of tetrahydrobenzo[<em>b</em>]pyran and dihydropyrano[3,2-<em>c</em>]chromene derivatives. These synthesized derivatives are an important class of heterocyclic scaffolds and exhibit significant potential as anti-coagulant, diuretic, spasmolytic, anticancer, and anti-anaphylactic agents. The prepared MNP-based catalysts were characterized using XRD, FE-SEM, VSM, TG-DTA, and Raman spectroscopy. The synthesis of derivatives involved the condensation reaction of enolizable compounds with aldehyde, dimedone, and ethyl cyanoacetate for tetrahydrobenzo[<em>b</em>]pyran, and the reaction of aromatic aldehyde, 4-hydroxycoumarin, and malononitrile for dihydropyrano[3,2-<em>c</em>]chromene synthesis. The reaction was optimized using different techniques such as stirring, ultrasonication, and microwave irradiation, with microwave irradiation method demonstrating faster product separation and high yield. The homogeneity of the isolated product was analyzed by FT-IR,<sup>1</sup>H-<sup>13</sup>C-NMR, and mass spectrometry. The advantages of this method include its simplicity, eco-friendliness, cost-effectiveness, and it also evades the use of toxic metals and solvents. The product is easily isolated through a simple workup process and recrystallization using ethanol yields pure product isolation.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 60-79"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142204211","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 : 2025-01-02DOI: 10.1080/10406638.2024.2390624
Parisa Sadighara
Polycyclic aromatic hydrocarbons (PAHs) are a group of complex chemicals that are formed and released during incomplete combustion during industrial processes or pyrolysis of the organic matter. Human exposure to PAHs primarily occurs through food consumption. One of the possible causes of formation in food is free radicals. Also, the confirmed mechanism of their toxicity in living organisms is oxidative stress. This complication is also caused by free radicals released during their metabolism. Chronic exposure to PAHs can lead to carcinogenic, teratogenic and mutagenic effects in humans. Consequently, there is a need to minimize the presence of these compounds in food. Research suggests that antioxidants play a crucial role in reducing PAH levels in food. Therefore, formulating food products with the right combination of antioxidants could be an effective strategy to mitigate the formation of PAHs. Moreover, antioxidants have been found to alleviate the toxicity associated with PAHs in the human body. This manuscript discusses the effects and mechanisms of antioxidants in reducing PAH in food products and living organisms.
{"title":"Antioxidants as Modulators of PAH Contaminants in Food and Living Organisms: An Overview Study","authors":"Parisa Sadighara","doi":"10.1080/10406638.2024.2390624","DOIUrl":"10.1080/10406638.2024.2390624","url":null,"abstract":"<div><div>Polycyclic aromatic hydrocarbons (PAHs) are a group of complex chemicals that are formed and released during incomplete combustion during industrial processes or pyrolysis of the organic matter. Human exposure to PAHs primarily occurs through food consumption. One of the possible causes of formation in food is free radicals. Also, the confirmed mechanism of their toxicity in living organisms is oxidative stress. This complication is also caused by free radicals released during their metabolism. Chronic exposure to PAHs can lead to carcinogenic, teratogenic and mutagenic effects in humans. Consequently, there is a need to minimize the presence of these compounds in food. Research suggests that antioxidants play a crucial role in reducing PAH levels in food. Therefore, formulating food products with the right combination of antioxidants could be an effective strategy to mitigate the formation of PAHs. Moreover, antioxidants have been found to alleviate the toxicity associated with PAHs in the human body. This manuscript discusses the effects and mechanisms of antioxidants in reducing PAH in food products and living organisms.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 123-135"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142252797","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 : 2025-01-02DOI: 10.1080/10406638.2024.2370570
Mohamed S. Abdel-Aziz , Ashraf A. Sediek , Anhar Abdel-Aziem
A new series of 1,3,4-thiadiazole linked to sulfa-azo derivatives via hydrazono-methyl bridge were synthesized via the reaction of methyl ((E)-(sulfa-derivatives)diazenyl) benzylidene)hydrazine-1-carbodithioates 1a-e with ethyl ester and acetyl hydrazonyl halides 2a-d. The chemical structures of the newly 1,3,4-thiadiazoles 3a-t have been clarified considring their elemental and spectral analysis. Antimicrobial activity of the newly 1,3,4-thiadiazoles was determined for Staphylococcus aureus, Escherichia coli, Candida albicans, as well as Aspergillus niger using the cup agar plate diffusion method. Out of the twenty compounds, compounds 3j, 3k, 3l, and 3s with isoxazole sulfonamides were selected for MIC assay. Compound 3j was equipotent with neomycin control drug against all tested strains, while compound 3k was 4-fold higher than neomycin against S. aureus, E. coli, and C. albicans with MIC values of 9.77, 19.53, and 19.53 μg/mL, respectively. Compound 3l was equipotent with neomycin against S. aureus and C. albicans, while it was 2-fold higher than neomycin against E. coli with MIC of 39.06 μg/mL. For 3s, it was less potent than neomycin against all tested microbs with 2-fold and 4-fold less potent. Further scanning electron microscopy (SEM) investigation has been studied to reveal the disruption effect of the selected potent antimicrobial compound (3k) on the intact cells of tested microbs S. aureus, E. coli in addition to C. albicans. Results showed that 3k exhibited a noticeable effect on destroying microbial cell walls. Furthermore, molecular docking study has been done to assess the binding behavior of two most effective compounds 3k and 3l with the target crystal structure of dihydropteroate synthase (PDB: 6CLV for S. aureus) and (PDB: 5U14 for E. coli). Compound 3k was shown to be able to form stable complexes with both target enzymes of dihydropteroate synthase through hydrogen bonding and hydrophobic interactions.
研究人员通过甲基((E)-(磺胺衍生物)偶氮)亚苄基)肼-1-c...
{"title":"Antimicrobial and Molecular Docking Studies of 1,3,4-Thiadiazole Tethered Sulfa-Azo Derivatives via Hydrazono-Methyl Bridge","authors":"Mohamed S. Abdel-Aziz , Ashraf A. Sediek , Anhar Abdel-Aziem","doi":"10.1080/10406638.2024.2370570","DOIUrl":"10.1080/10406638.2024.2370570","url":null,"abstract":"<div><div>A new series of 1,3,4-thiadiazole linked to sulfa-azo derivatives <em>via</em> hydrazono-methyl bridge were synthesized <em>via</em> the reaction of methyl ((<em>E</em>)-(sulfa-derivatives)diazenyl) benzylidene)hydrazine-1-carbodithioates <strong>1a-e</strong> with ethyl ester and acetyl hydrazonyl halides <strong>2a-d</strong>. The chemical structures of the newly 1,3,4-thiadiazoles <strong>3a-t</strong> have been clarified considring their elemental and spectral analysis. Antimicrobial activity of the newly 1,3,4-thiadiazoles was determined for <em>Staphylococcus aureus</em>, <em>Escherichia coli, Candida albicans,</em> as well as <em>Aspergillus niger</em> using the cup agar plate diffusion method. Out of the twenty compounds, compounds <strong>3j</strong>, <strong>3k</strong>, <strong>3l,</strong> and <strong>3s</strong> with isoxazole sulfonamides were selected for MIC assay. Compound <strong>3j</strong> was equipotent with neomycin control drug against all tested strains, while compound <strong>3k</strong> was 4-fold higher than neomycin against <em>S. aureus</em>, <em>E. coli</em>, and <em>C. albicans</em> with MIC values of 9.77, 19.53, and 19.53 μg/mL, respectively. Compound <strong>3l</strong> was equipotent with neomycin against <em>S. aureus</em> and <em>C. albicans,</em> while it was 2-fold higher than neomycin against <em>E. coli</em> with MIC of 39.06 μg/mL. For <strong>3s</strong>, it was less potent than neomycin against all tested microbs with 2-fold and 4-fold less potent. Further scanning electron microscopy (SEM) investigation has been studied to reveal the disruption effect of the selected potent antimicrobial compound (<strong>3k</strong>) on the intact cells of tested microbs <em>S. aureus, E. coli</em> in addition to <em>C. albicans</em>. Results showed that <strong>3k</strong> exhibited a noticeable effect on destroying microbial cell walls. Furthermore, molecular docking study has been done to assess the binding behavior of two most effective compounds <strong>3k</strong> and <strong>3l</strong> with the target crystal structure of dihydropteroate synthase (PDB: 6CLV for <em>S. aureus</em>) and (PDB: 5U14 for <em>E. coli</em>). Compound <strong>3k</strong> was shown to be able to form stable complexes with both target enzymes of dihydropteroate synthase through hydrogen bonding and hydrophobic interactions.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 1-18"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141504061","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}
Sulfur-containing heterocyclic compounds have emerged as an important class of bioactive molecules in drug discovery owing to their diverse pharmacological activities and unique modes of action. Sulfur drugs exert their pharmacological actions primarily through their ability to interfere with microbial growth and modulate immune responses. The provided compounds showed a spectrum of heterocyclic ring structures of varying sizes, from three- to seven-membered rings, each influencing the medicinal potency of the compounds. Smaller rings, such as three- and four-membered rings, often impart unique reactivity and functional properties, potentially leading to potent pharmacological effects. Conversely, larger rings, such as six- and seven-membered rings, may offer increased structural stability and favorable interactions with biological targets, enhancing the medicinal potency of the compounds. Understanding the relationship between ring size and medicinal potency is crucial in drug design to facilitate the development of therapeutics with optimized efficacy and pharmacokinetic properties. This review provides a comprehensive overview of drugs that contain sulfur-containing heterocyclic compounds as key structural motifs, modes of action, and interactions with specific protein targets, enzymes, receptors, and cellular processes. Moreover, we highlight their potential as drug candidates for treating numerous diseases and highlight their significance in drug discovery research.
含硫杂环化合物因其多样的药理活性和独特的作用模式，已成为药物发现中一类重要的生物活性分子。苏...
{"title":"Drugs and Their Mode of Action: A Review on Sulfur-Containing Heterocyclic Compounds","authors":"Kanchan Kapoor , Navneet Kaur , Harvinder Singh Sohal , Manvinder Kaur , Kishanpal Singh , Asim Kumar","doi":"10.1080/10406638.2024.2392781","DOIUrl":"10.1080/10406638.2024.2392781","url":null,"abstract":"<div><div>Sulfur-containing heterocyclic compounds have emerged as an important class of bioactive molecules in drug discovery owing to their diverse pharmacological activities and unique modes of action. Sulfur drugs exert their pharmacological actions primarily through their ability to interfere with microbial growth and modulate immune responses. The provided compounds showed a spectrum of heterocyclic ring structures of varying sizes, from three- to seven-membered rings, each influencing the medicinal potency of the compounds. Smaller rings, such as three- and four-membered rings, often impart unique reactivity and functional properties, potentially leading to potent pharmacological effects. Conversely, larger rings, such as six- and seven-membered rings, may offer increased structural stability and favorable interactions with biological targets, enhancing the medicinal potency of the compounds. Understanding the relationship between ring size and medicinal potency is crucial in drug design to facilitate the development of therapeutics with optimized efficacy and pharmacokinetic properties. This review provides a comprehensive overview of drugs that contain sulfur-containing heterocyclic compounds as key structural motifs, modes of action, and interactions with specific protein targets, enzymes, receptors, and cellular processes. Moreover, we highlight their potential as drug candidates for treating numerous diseases and highlight their significance in drug discovery research.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 136-175"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142204208","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 : 2025-01-02DOI: 10.1080/10406638.2024.2384901
Pradeepa A. , Arathi P.
Topological indices are well-known molecular descriptors that may be applied to any graph and to model specific molecular structures, utilized for property correlation in quantitative structure activity and property relationship (QSAR and QSPR) analyses. Strong methods for machine learning information and thermodynamic simulations of massive networks and nanomaterials can be facilitated by using topological indices. Kekulenes are a novel type of cycloarenes, arranged in doughnut-shaped cyclic benzene rings with riveting superaromaticity and other significant properties. The main aim of this paper is to ascertain the notable degree and the neighborhood degree sum-based indices through M-polynomials and neighborhood M-polynomials of certain types of tessellations of kekulenes. Then, a graphical comparison of the resulting indices is also performed.
{"title":"Computing Degree-Based Topological Descriptors of Certain Tessellations of Kekulenes Using M-Polynomial and Neighborhood M-Polynomial","authors":"Pradeepa A. , Arathi P.","doi":"10.1080/10406638.2024.2384901","DOIUrl":"10.1080/10406638.2024.2384901","url":null,"abstract":"<div><div>Topological indices are well-known molecular descriptors that may be applied to any graph and to model specific molecular structures, utilized for property correlation in quantitative structure activity and property relationship (QSAR and QSPR) analyses. Strong methods for machine learning information and thermodynamic simulations of massive networks and nanomaterials can be facilitated by using topological indices. Kekulenes are a novel type of cycloarenes, arranged in doughnut-shaped cyclic benzene rings with riveting superaromaticity and other significant properties. The main aim of this paper is to ascertain the notable degree and the neighborhood degree sum-based indices through M-polynomials and neighborhood M-polynomials of certain types of tessellations of kekulenes. Then, a graphical comparison of the resulting indices is also performed.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 36-59"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141944759","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 : 2025-01-02DOI: 10.1080/10406638.2024.2380996
Paul Awolade , Pule Seboletswe , Parvesh Singh
A new library of quinoline–natural product conjugates bearing 1,2,3-triazole moiety as a linker has been synthesized using the copper(I) catalyzed azide-alkyne [3 + 2] cycloaddition reaction (CuAAC) methodology. The structure characterization of the synthesized compounds was achieved using NMR and HRMS analysis. The compounds were subsequently screened for their antimicrobial efficacies against methicillin resistant Staphylococcus aureus (MRSA), MDR Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and Cryptococcus neoformans. The studied compounds generally displayed stronger inhibition of microbial cell growth compared to their parent phenolic natural products. Eugenol, thymol, guaiacol, and o-vanillin based 1H-1,2,3-triazole compounds exhibited the best antimicrobial profiles while the pathogen, A. baumannii showed the highest susceptibility to the hybrids. Precisely, hybrids 19a, 20b, and 25b derived from eugenol, thymol, and o-vanillin, respectively, exhibited over 50% growth inhibition of the pathogen. K. pneumoniae was however strongly resistant to the compound series. In silico docking studies of the representative compounds further explored the characteristic binding orientations of these compounds in the active sites of the bacterial and fungal proteins. Overall, we perceive that rational scaffold hopping of these compounds holds promise to offer novel antimicrobial agents with enhanced potency.
利用铜（I）催化的叠氮-炔烃[3 + 2]环加成反应（CuAAC...
{"title":"Synthesis and Antimicrobial Evaluation of 1H-1,2,3-Triazole-Linked Quinoline-Phenolic Natural Product Conjugates","authors":"Paul Awolade , Pule Seboletswe , Parvesh Singh","doi":"10.1080/10406638.2024.2380996","DOIUrl":"10.1080/10406638.2024.2380996","url":null,"abstract":"<div><div>A new library of quinoline–natural product conjugates bearing 1,2,3-triazole moiety as a linker has been synthesized using the copper(I) catalyzed azide-alkyne [3 + 2] cycloaddition reaction (CuAAC) methodology. The structure characterization of the synthesized compounds was achieved using NMR and HRMS analysis. The compounds were subsequently screened for their antimicrobial efficacies against methicillin resistant <em>Staphylococcus aureus</em> (MRSA), MDR <em>Klebsiella pneumoniae</em>, <em>Acinetobacter baumannii</em>, <em>Pseudomonas aeruginosa</em>, <em>Escherichia coli, Candida albicans,</em> and <em>Cryptococcus neoformans</em>. The studied compounds generally displayed stronger inhibition of microbial cell growth compared to their parent phenolic natural products. Eugenol, thymol, guaiacol, and <em>o</em>-vanillin based 1<em>H</em>-1,2,3-triazole compounds exhibited the best antimicrobial profiles while the pathogen, <em>A. baumannii</em> showed the highest susceptibility to the hybrids. Precisely, hybrids <strong>19a</strong>, <strong>20b</strong>, and <strong>25b</strong> derived from eugenol, thymol, and <em>o</em>-vanillin, respectively, exhibited over 50% growth inhibition of the pathogen. <em>K. pneumoniae</em> was however strongly resistant to the compound series. <em>In silico</em> docking studies of the representative compounds further explored the characteristic binding orientations of these compounds in the active sites of the bacterial and fungal proteins. Overall, we perceive that rational scaffold hopping of these compounds holds promise to offer novel antimicrobial agents with enhanced potency.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 19-35"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141944758","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-02DOI: 10.1080/10406638.2024.2391486
El Hassane Anouar , Insaf Filali , Syed Adnan Ali Shah , Khalid Karrouchi
In the present work, five pyrazole-hydrazone biomolecule ligands (L1–L5) were synthesized by condensation between 1H-pyrazole-3-carbohydrazide (2) and aromatic benzaldehydes. Their corresponding structures were elucidated employing NMR and FT-IR spectra and ESI-MS data. Li-Cu(II) complexes (i = 1–5) were evaluated for catecholase activity in situ at standard conditions. The findings disclose that the catecholase oxidation rate varies with the substituted functional groups in ligand and the anion type in the copper (II) salt. Catecholase activity results showed that the L(i = 1–5) -Cu(II)SO4 complexes exhibited efficient catalytic activity, and a maximum activity of 105 ± 42 µM.min−1 is obtained with L5-Cu(II)SO4. DFT and NBO calculations have been carried out to identify the global reactivity and the strength of interaction bonds between the donors and acceptors in L1–L5. The optimized structure of L1–L3 and L5 were found planar, while that of L4 is out of the molecular plan and forms a torsion angle of 18 degrees due to the presence of methoxy and hydroxyl group at meta and para. In L4, the 5-methyl-1H-pyrazole moiety. NBO findings show that the strongest interactions in L1–L5 are those involved in the electronic transition from π-bonding → π*-antibonding and LP → π*- antibonding molecular orbitals. Further, the anti-SARS-CoV-2 of L1–L5 are investigated by estimating their binding affinities into its binding. The docking results reveal that L1–L5 may act as SARS-CoV-2 main protease inhibitors with estimated binding energies in the −6.00 to −8.0 kcal.mol−1 range.
{"title":"Synthesis, Spectroscopic Characterization, DFT, Molecular Docking, Catechol Oxidase Activity, and Anti-SARS-CoV-2 of Acylhydrazone Derivatives","authors":"El Hassane Anouar , Insaf Filali , Syed Adnan Ali Shah , Khalid Karrouchi","doi":"10.1080/10406638.2024.2391486","DOIUrl":"10.1080/10406638.2024.2391486","url":null,"abstract":"<div><div>In the present work, five pyrazole-hydrazone biomolecule ligands (<strong>L1–L5</strong>) were synthesized by condensation between <em>1H</em>-pyrazole-3-carbohydrazide (<strong>2</strong>) and aromatic benzaldehydes. Their corresponding structures were elucidated employing NMR and FT-IR spectra and ESI-MS data. <strong>Li-Cu(II)</strong> complexes (<em>i</em> = 1–5) were evaluated for catecholase activity <em>in situ</em> at standard conditions. The findings disclose that the catecholase oxidation rate varies with the substituted functional groups in ligand and the anion type in the copper (II) salt. Catecholase activity results showed that the <strong>L</strong>(<em>i</em> = 1–5) -Cu(II)SO<sub>4</sub> complexes exhibited efficient catalytic activity, and a maximum activity of 105 ± 42 µM.min<sup>−1</sup> is obtained with <strong>L5</strong>-Cu(II)SO<sub>4</sub>. DFT and NBO calculations have been carried out to identify the global reactivity and the strength of interaction bonds between the donors and acceptors in <strong>L1–L5</strong>. The optimized structure of <strong>L1</strong>–<strong>L3</strong> and <strong>L5</strong> were found planar, while that of <strong>L4</strong> is out of the molecular plan and forms a torsion angle of 18 degrees due to the presence of methoxy and hydroxyl group at <em>meta</em> and <em>para</em>. In <strong>L4</strong>, the 5-methyl-1H-pyrazole moiety. NBO findings show that the strongest interactions in <strong>L1–L5</strong> are those involved in the electronic transition from π-bonding → π*-antibonding and LP → π*- antibonding molecular orbitals. Further, the anti-SARS-CoV-2 of <strong>L1–L5</strong> are investigated by estimating their binding affinities into its binding. The docking results reveal that <strong>L1–L5</strong> may act as SARS-CoV-2 main protease inhibitors with estimated binding energies in the −6.00 to −8.0 kcal.mol<sup>−1</sup> range.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 80-97"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142204209","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 : 2025-01-02DOI: 10.1080/10406638.2024.2387615
Jeelan Basha Nagenahalli , Prashanth Reddiyappa , Akshay K Thammaiah
Benzimidazole is one of the heterocycles associated with diverse biological potential such as anthelmintic, antacid, antimicrobial, anticancer, and antiviral. Based on the importance of this moiety in medicinal drugs, both clinically approved and in clinical trials, many novel synthetic approaches have been reported for benzimidazoles. Nonetheless, there is a need for novel benzimidazoles to overcome drug resistance and side effects. The present review covers the recent reports on benzimidazole synthesis using a different strategy, our work on the synthesis, and biologically potent novel benzimidazoles.
{"title":"Synthesis of Pharmacologically Potent Benzimidazole Analogs","authors":"Jeelan Basha Nagenahalli , Prashanth Reddiyappa , Akshay K Thammaiah","doi":"10.1080/10406638.2024.2387615","DOIUrl":"10.1080/10406638.2024.2387615","url":null,"abstract":"<div><div>Benzimidazole is one of the heterocycles associated with diverse biological potential such as anthelmintic, antacid, antimicrobial, anticancer, and antiviral. Based on the importance of this moiety in medicinal drugs, both clinically approved and in clinical trials, many novel synthetic approaches have been reported for benzimidazoles. Nonetheless, there is a need for novel benzimidazoles to overcome drug resistance and side effects. The present review covers the recent reports on benzimidazole synthesis using a different strategy, our work on the synthesis, and biologically potent novel benzimidazoles.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 1","pages":"Pages 106-122"},"PeriodicalIF":2.4,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142204212","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 : 2024-11-25DOI: 10.1080/10406638.2023.2284796
R. Suja , A. Rathika , Joselin Beaula T. , Arun Kumar A.
In the present work a new organic single crystal Benzotriazole (BTSA) was synthesized and fully characterized by means of single crystal XRD, FT-IR, FT-Raman and UV-visible spectroscopic techniques. Single-crystal X-ray diffraction was applied to the growing crystal to determine the cell dimensions. It has been found that the HOMO and LUMO computed energies accurately depict the characteristics of electron excitation. The TD-DFT approach was used to analyze the UV-visible spectra and study spectroscopic wavenumbers. Analysis using the quantum theory of atoms in molecules has been done to find all potential non-covalent interactions. Multiwfn has been used to visualize Electron Localization Function (ELF) and Localized Orbital Locator (LOL) to examine the molecule’s electrical characteristics. Antimicrobial activity studies indicate the compound good antibacterial and antifungal activity. The docking parameters were studied with Candida tropicalis proteins and the lowest binding energy −5.95 kcal/mol has been achieved for 6ZD2 protein.
{"title":"Synthesis, Physiochemical Characterization and Biological Investigation with Quantum Chemical Computations of Benzotriazole Salicylate","authors":"R. Suja , A. Rathika , Joselin Beaula T. , Arun Kumar A.","doi":"10.1080/10406638.2023.2284796","DOIUrl":"10.1080/10406638.2023.2284796","url":null,"abstract":"<div><div>In the present work a new organic single crystal Benzotriazole (BTSA) was synthesized and fully characterized by means of single crystal XRD, FT-IR, FT-Raman and UV-visible spectroscopic techniques. Single-crystal X-ray diffraction was applied to the growing crystal to determine the cell dimensions. It has been found that the HOMO and LUMO computed energies accurately depict the characteristics of electron excitation. The TD-DFT approach was used to analyze the UV-visible spectra and study spectroscopic wavenumbers. Analysis using the quantum theory of atoms in molecules has been done to find all potential non-covalent interactions. Multiwfn has been used to visualize Electron Localization Function (ELF) and Localized Orbital Locator (LOL) to examine the molecule’s electrical characteristics. Antimicrobial activity studies indicate the compound good antibacterial and antifungal activity. The docking parameters were studied with Candida tropicalis proteins and the lowest binding energy −5.95 kcal/mol has been achieved for 6ZD2 protein.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 10","pages":"Pages 6737-6764"},"PeriodicalIF":2.4,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138504150","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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