Polycyclic Aromatic Compounds最新文献

{"title":"Synthesis, Spectral Analysis, DFT Calculations, in Vitro Screening, and Molecular Docking of New Metal Complexes with Quinoline and Isoniazid Schiff Base as Antimicrobial and Antioxidant Agents","authors":"","doi":"10.1080/10406638.2023.2265024","DOIUrl":"10.1080/10406638.2023.2265024","url":null,"abstract":"<div><div>We herein report the synthesis, spectral analysis, DFT calculations, <em>in vitro</em> and <em>in silico</em> biological activities of novel <em>N</em>'-((2-thioxo-1,2-dihydroquinolin-3 yl)methylene)isonicotinohydr-azide with its Cu(II), Co(II), Ni(II), and Zn(II) complexes have been successfully prepared. The ligand and the complexes were characterized by analytical, FT-IR, ¹H NMR, mass, UV–visible spectroscopy, molar conductivity, and magnetic susceptibility measurements. Density Functional Theory (DFT) estimations for the ligand at the DFT/B3LYP level <em>via</em> 6-31 G⁺⁺ (d, p) replicate the structure and geometry. Furthermore, molecular docking and ADME calculations were also performed to correlate and interpret the experimental results. The antimicrobial activity study illustrated enhancement in the activity of the free ligand upon complex formation, and the Cu(II) complex (MIC 25 µg mL⁻¹) may be considered a promising antibacterial agent, and Ni(II) and Zn(II) complexes (MIC 25 µg mL⁻¹) as promising antifungal agent. Also, synthesized Ni(II) and Zn(II) metal complexes (MIC 3.125 µg mL⁻¹) showed promising anti-TB activity against <em>Mycobacterium tuberculosis.</em> In the antioxidant activity, the Cu(II) complex showed excellent activity as compared to standard drugs and <em>in silico</em> docking studies were carried out against <em>Cytochrome c Peroxidase</em> (PDB ID: 2X08).</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136295647","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}

{"title":"Formation of Inclusion Complexes of 2-Hydroxypropyl β-Cyclodextrin with 2-Hydroxychalcone: Experimental and Theoretical Study","authors":"","doi":"10.1080/10406638.2023.2259565","DOIUrl":"10.1080/10406638.2023.2259565","url":null,"abstract":"<div><div>The formation of inclusion complexes of 2-hydroxypropyl-β-cyclodextrin (HP β-CD) with 2-hydroxychalcone (2HOCH) in solution and solid state was investigated using UV–Visible, fluorescence, Fourier transform-infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscope (SEM) techniques. The results obtained confirmed that 2HOCH formed the stable inclusion complex with HP β-CD. Moreover, the spectral data and Benesi–Hildebrand plots results indicated that the stoichiometry of the inclusion complex was 1:1. Theoretically, the structure of the inclusion complexes and the physical parameters such as complexation energy, highest occupied molecular orbital–lowest unoccupied molecular orbital, and energy gap were obtained using the DFT/B3LYP/6-311G method. It was found that the complexation energy for orientation B was lower than that for orientation A as evidenced by the theoretical calculations. Moreover, the carbonyl group of molecules was located outside of the cyclodextrin cavity while the hydroxyl group was located inside the cavity. The antioxidant capacity and antibacterial responses of the inclusion complexes and, for comparison, the parent compounds were also carried out.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135093718","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}

{"title":"Transmittal Effect Evaluation of Heterocyclic Rings on Nonlinear Optical Ambit of Benzotrithiophene-Based Push-Pull Driving Materials: a Theoretical Approach","authors":"","doi":"10.1080/10406638.2023.2264451","DOIUrl":"10.1080/10406638.2023.2264451","url":null,"abstract":"<div><div>To obtain extensive insights into NLO properties, herein, two series of benzotrithiophene (<strong>BTT</strong>) based organic compounds (<strong>MS1-MS5</strong> and <strong>MP1-MP5</strong>) containing D₁-<em>π</em>₁-D₂-<em>π</em>₂-A-type framework have been designed. The structural tailoring was accomplished <em>via</em> the incorporation of thiophene and pyrrole units in <strong>MS1-MS5</strong> and <strong>MP1-MP5</strong>, respectively at the region of <em>π</em>₂ in each derivative. Quantum chemical calculations including: frontier molecular orbitals (FMOs), natural population analysis (NPA), UV-Vis investigation, transition density matrix (TDMx), density of state (DOS), molecular electrostatic potential (MEP) and natural bond orbitals (NBOs) analyses were accomplished at MPW1PW91/6-311G(d,p) functional to determine the influence of <em>π</em>-linkers on the optical response of designed chromophores. Conclusively, remarkable NLO results were obtained for thiophene-based derivatives (<strong>MS1-MS5</strong>) as compared to pyrrole-based derivatives (<strong>MP1-MP5</strong>). Interestingly, among all the derivatives, minimum <em>E gap</em> values of 2.248 and 2.264 <em>eV</em> were observed for <strong>MS4</strong> and <strong>MS5</strong>, respectively, and the <em>E gap</em> values were found in the following decreasing order: <strong>MS1</strong>&gt;<strong>MS3</strong>&gt;<strong>MS2</strong>&gt;<strong>MS5</strong>&gt;<strong>MS4</strong>. Surprisingly, <strong>MS4</strong> and <strong>MS5</strong> displayed maximum amplitudes of <em>&lt; α&gt; i.e.,</em> 2.44 × 10⁻²² and 2.65 × 10⁻²²<em>esu</em> as well as &lt; <em>γ</em>&gt; such as: 3.91 × 10⁻³² and 4.35 × 10⁻³²<em>esu</em>, respectively. Moreover, the declining trend of &lt; <em>γ</em>&gt; was observed as follows: <strong>MS5 </strong>&gt;<strong> MS4 </strong>&gt;<strong> MS2 </strong>&gt;<strong> MS3 </strong>&gt;<strong> MS1</strong>. In a nutshell, this investigation may provide a new insight for the use of these <strong>BTT</strong>-based organic chromophores especially <strong>MS4</strong> and <strong>MS5</strong> for potential NLO-based hi-tech applications.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135095819","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}

{"title":"Green Synthesis of Arylideneisoxazol-5-Ones Catalyzed by Silicon Dioxide Nanoparticles","authors":"","doi":"10.1080/10406638.2023.2259564","DOIUrl":"10.1080/10406638.2023.2259564","url":null,"abstract":"<div><div>4-Arylideneisoxazol-5(4<em>H</em>)-ones were obtained <em>via</em> a simple and efficient one-pot, three-component cyclocondensation of diverse aldehydes with hydroxylamine hydrochloride and <em>β</em>-keto esters in water. This one-pot heterocyclization has been performed in the presence of catalytic amounts of silicon dioxide nanoparticles (SiO₂ NPs) at room temperature. This approach is economical for the synthesis of potentially bioactive 4-arylideneisoxazol-5(4<em>H</em>)-one derivatives. The products were formed in 86–94% isolated reaction yields using 5 mol% nanocatalyst. The heterocyclization reactions were completed at room temperature under aqueous conditions. The significant features of the present procedure are uncomplicated product isolation, purification without chromatographic methods, great biocompatibility of SiO₂ NPs, straightforward reaction conditions, easy workup, environmentally friendly, readily available starting materials, reusability of the catalyst, as well as inexpensive and green reaction medium.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136136687","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}

{"title":"Synthesis, DFT, in silico anticancer, ADME and toxicity prediction study of (E)-2-(2-(3,4-dihydronaphthalen-1(2H)- ylidene)hydrazineyl)-4-(4-methoxyphenyl)thiazole","authors":"","doi":"10.1080/10406638.2023.2266091","DOIUrl":"10.1080/10406638.2023.2266091","url":null,"abstract":"<div><div>In the current paper, we describe computational molecular modeling to investigate the quantum chemical, spectroscopic, MESP and in-silico Anticancer, ADME and toxicity study of (<em>E</em>)-2-(2-(3,4-dihydronaphthalen-1(<em>2H</em>)-ylidene)hydrazineyl)-4-(4-methoxyphenyl)thiazole by one pot three component reaction. DFT method with B3LYP/6-311G(d,p) level was used to optimize the geometry, molecular electrostatic potential (MESP), Mulliken charges and vibrational assignments. The UV-Vis assignments, frontier molecular orbital (FMO), electronic parameters, and global descriptor were studied using the TD-DFT method with CAM-B3LYP/6-311G(d,p) level. In-silico anticancer study revealed favorable binding interaction with an excellent docking score comparable to the anticancer drug Dasatinib. The molecular docking study found that, target 4xt2 receptor’s amino acid residues VAL422B, LEU407D, MET426D, TYR327A, GLN421B, SER424B, and LEU423D play a vital role. The title compound has the requisite toxicity and ADME profiles, and it has the potential to be therapeutic.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135412713","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}

{"title":"Impact of π-Linkers Modifications on Tuning Nonlinear Optical Amplitudes of Pyridoquinazolinone-Based Aromatic Dyes: A Rational Entry to Novel D-π-A NLO Materials","authors":"","doi":"10.1080/10406638.2023.2266093","DOIUrl":"10.1080/10406638.2023.2266093","url":null,"abstract":"<div><div>Developing efficient nonlinear optical (NLO) materials is a cutting-edge field of study. The desirability of promising NLO materials for optoelectronic applications drove us to investigate the pyridoquinazolinone-based D-π-A architectured chromophores for predicting proficient NLO compounds. Pyridoquinazolinone-based dye (WL-O) is chosen as a reference and its nine derivatives (ASH1-ASH9) are quantum chemically modeled by inserting variously reported π-linkers into the D-π-A framework. Simulations using DFT and TD-DFT provide insight into how π-linker alteration affects the NLO properties. The potential use of investigated dyes for NLO response applications is confirmed by evaluating photophysical aspects, frontier molecular orbital (FMO), natural population analysis (NPA), molecular electrostatic potential (MEP), the density of state (DOS), transition density matrix (TDM) analysis, and static, frequency-dependent NLO response properties. FMO analysis shows that all dyes’ energy gaps are lower when compared to the reference, resulting in a strong NLO response. The highest absorption wavelength of the studied dyes was found to be in the visible spectrum, as determined by UV-Vis analysis. NPA-based findings demonstrated the movement of the electrons from D to A through π-linkers resulting in the formation of a charge separation state and active NLO sensitivity of the proposed dyes. Moreover, MEP, LOL, and ELF topological investigations are performed to appraise the charge transfer inside ASH1-ASH9 and high NLO characteristics. The robust NLO response revealed the eye-catching linear polarizability(<em>α 0</em>), first-hyperpolarizability (<em>β</em>), particularly ASH3, with the highest <em>α 0</em> and <em>β 0</em> computed to be 520.44 a.u. and 26166.79 a.u., respectively. Additionally, frequency-dependent hyperpolarizability SHG <em>β</em>(−2<em>ω</em>,<em>ω</em>,<em>ω</em>) and EOPE <em>β</em>(−<em>ω</em>,<em>ω</em>,0) calculations for commonly used lasers were performed at 1907.21, 532, and 1064 nm. ASH3 with terthiophene linker exhibits a striking EOPE <em>β</em>(−<em>ω</em>,<em>ω</em>,0) and SHG <em>β</em>(−2<em>ω</em>,<em>ω</em>,<em>ω</em>) response of 2.94 × 10⁴ a.u. and 3.80 × 10⁴ a.u. respectively at 1907.21 nm. This theoretical framework confirmed that the investigated dyes have fine NLO potential and are recommended for future NLO applications.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135766621","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}

{"title":"Synthesis and Characterization of Novel 2D Ultrathin Nanoribbons Cd-Ag-MOF@ZnO Composite as Organo-Nanocatalyst for Preparation of Polyhydroquinoline Heterocycles","authors":"","doi":"10.1080/10406638.2023.2261596","DOIUrl":"10.1080/10406638.2023.2261596","url":null,"abstract":"<div><div>Novel ultrathin Cd-Ag-MOF@ZnO composite nanoribbons (Ut-Nr Cd-Ag-MOF@ZnO C) were prepared and characterized in this research to serve as organocatalyst in Hantzsch condensation for selective synthesis of asymmetric polyhydroquinolines through a one-pot multi-component condensation reaction of various substituted arylaldehyde, 5,5-dimethyl-1,3-cyclohexanedione, ammonium acetate and ethyl acetoacetate under solvent-free conventional heating in relatively short reaction times. The developed catalysts were easily recycled and reutilized at least three times under optimized reaction conditions with no noticeable decline in their initial catalytic activities. Operational simplicity and environmental compatibility, combined with the application of a reusable and affordable heterogeneous catalyst, significant efficiency, relatively short reaction time, and good yield are among the main characteristics of the proposed synthetic approach.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135898769","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}

{"title":"Efficient and Facile One-Pot Multi-Component Synthesis of Betti Bases Using Baker’s Yeast for the First Time","authors":"","doi":"10.1080/10406638.2023.2265022","DOIUrl":"10.1080/10406638.2023.2265022","url":null,"abstract":"<div><div>A green and facile synthesis of 1-(α-aminoalkyl)-2-naphthols, generally called Betti bases (BB) in the presence of Baker’s yeast (BY), acts as an efficient catalyst, and ethanol as a green solvent. In this methodology, the BY is used first time as a biocatalyst (enzyme). This protocol has some inherent advantages, such as mild reaction conditions, no environmental pollution, simple work up, no need of column chromatography, diversity of reactant and desired 1-(α-aminoalkyl)-2-naphthols (Betti bases) (<strong>4a-r</strong>) are obtained in good-to-excellent yields. This is the first report on Baker’s yeast-catalyzed (BYC) synthesis for BB. This present bio-catalytical route for synthesizing BB in the presence of biocatalysts like BY is anticipated to open a gateway to synthesized complexed biological active molecules counting BB.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135896039","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}

{"title":"One Pot Synthesis, Crystal Structure, Hirshfeld Studies, Docking Simulation and Antimicrobial Efficacy Assay of New Fused/Substituted Pyrazolinyl–Thiazolidinyl–Indolone Triheterocyclic Hybrid Scaffolds","authors":"","doi":"10.1080/10406638.2023.2261585","DOIUrl":"10.1080/10406638.2023.2261585","url":null,"abstract":"<div><div>In this present investigation, a new series of functionalized hybrid compounds containing three bioactive triheterocyclic templates, pyrazolines, thiazolidinones, and indolones are designed and synthesized <em>via</em> multicomponent, one-pot reaction of 3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]-4,5-dihydro-1<em>H</em>-pyrazole-1-carbothioamide with various substituted isatin derivatives and chloroacetic acid in the presence of fused sodium acetate and glacial acetic acid <em>viz</em> ring closure mechanism followed by dehydration. The formation of new scaffolds <strong>4–7(a–c)</strong> is evidenced by analytical and spectral studies. The single-crystal X-ray diffraction study supported the molecular structure of compound <strong>4a</strong> as a triclinic crystal system with a <em>P</em><span><math><mrow><mrow><mover><mrow><mn>1</mn></mrow><mo>¯</mo></mover></mrow></mrow></math></span> space group and <em>Z</em> = 2. Interestingly, the compound is crystallized with two molecules (<em>A</em>/<em>B</em>) and one water molecule in the asymmetric unit, and the crystal packing is stabilized by intra and intermolecular hydrogen bonds. To quantify the percentage of intermolecular contacts and electrostatic potential distribution in crystal packing, Hirshfeld surface analysis was performed. All the compounds were screened for their preliminary antimicrobial activity against a panel of bacterial and fungal strains. The newly synthesized compounds exhibited fairly encouraging <em>in vitro</em> antibacterial activity, so the validation of the potent compound was done by docking against the antibacterial target <em>Escherichia coli</em> FabH (PDB: 5BNS). The virtual screening is focused on ADME and drug-likeliness properties to identify their putative ligand-protein interactions using Schrödinger software.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135246889","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}

{"title":"Microwave Assisted Greener and Eco-Friendly Approach for Synthesis of Functionalized 2-Arylbenzoxazoles, 2-Arylbenzothiazoles, and 2-Arylbenzimidazoles Using Waste Curd Water","authors":"","doi":"10.1080/10406638.2023.2265023","DOIUrl":"10.1080/10406638.2023.2265023","url":null,"abstract":"<div><div>Herein, we have designed a greener and efficient microwave-assisted route for the synthesis of functionalized 2-arylbenzoxazoles, 2-arylbenzothiazoles, and 2-arylbenzimidazoles. These compounds were produced through the condensation reaction involving 2-aminophenol, 2-aminothiophenol, and 1,2-phenylenediamine, respectively, with corresponding aldehydes. Remarkably, this reaction was conducted employing waste curd water as a catalytic solvent and under the influence of microwave radiation. Curd water, a liquid byproduct obtained from the coagulation process during cheese or yogurt production, was harnessed as catalytic solvent for the reaction. The application of emerging microwave-assisted chemistry techniques in combination with greener reaction media dramatically reduces reaction time as well as chemical waste. This investigation not only demonstrates a waste-to-wealth paradigm but also contributes to the mitigation of environmental waste.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135141818","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}