Polycyclic Aromatic Compounds最新文献

{"title":"Click Chemistry-Based Synthesis, Characterization, and DFT Studies of Some Novel 2-Acetylphenoxy-1,2,3-Triazoles","authors":"","doi":"10.1080/10406638.2023.2259567","DOIUrl":"10.1080/10406638.2023.2259567","url":null,"abstract":"<div><div>A series of the new 1,2,3-triazole-acetophenone hybrid system are synthesized from the click reaction between 1-(2-(prop-2-yn-1-yloxy)phenyl)ethan-1-one 1 and different azido benzene derivatives <strong>2-7</strong>. All compounds are characterized by ¹H NMR, ¹³C NMR, mass spectra, and elemental analyses. Field Emission Scanning Electron Microscope (FESEM) detected highly ordered aggregations, and the morphology of the compounds was determined, directed by van der Waals (vdW) forces and π-π stacking interactions. The Gaussian 09 and Gaussian view 6.0 softwares are used for all Density Functional Theory (DFT) calculations at the B3LYP. Band gap, molecular softness, electronegativity, and electrophilicity measurements show that molecule <strong>9</strong> is a soft molecule with higher polarizability, lower kinetic stability, and more chemical reactivity than the other molecules, which tend to be the most stable and least reactive. The molecules can be divided into two categories based on their chemical potential values: Although compound <strong>9</strong> looks to have more activity, compounds <strong>8</strong>, <strong>10</strong>, <strong>11</strong>, <strong>12</strong>, and <strong>13</strong> often have the best stability and least reactivity. According to the MEPs, the nitrogen and oxygen atoms are the electronegative potential sites in all compounds, while the hydrogen atoms in the alkyl and aromatic cyclic groups are the electropositive potential sites.</div></div><div><div><span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (396KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></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":"135814622","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":"Growth, Structural, Spectroscopic and Thermal Analyses of Novel Organic Brucinum-3, 5 –Dihydroxybenzoate Dihydrate Single Crystals for NLO Applications","authors":"","doi":"10.1080/10406638.2023.2263612","DOIUrl":"10.1080/10406638.2023.2263612","url":null,"abstract":"<div><div>Along the line of available efficient nonlinear optical (NLO) organic single crystals in the literature, it is worthwhile to bring in a novel organic single crystal of Brucinium-3,5-dihydroxybenzoate dihydrate (B35D) which was successfully grown utilizing the technique of slow evaporation of solution at ambient conditions. As the solubility of B35D was found to be the highest in water-ethanol 1:1 mixed solvent among the conventional solvents, crystallization of B35D was accomplished by making use of the solvent. The required confirmation of the crystal structure of the crystal and its lattice parameter could be achieved by the single-crystal X-ray diffraction analysis such that B35D was found to be crystallized in the monoclinic system with the non-centrosymmetric space group C2. The recording of UV-Vis-NIR transmittance spectrum of the crystal was undertaken between the range of 300 and 900 nm whereby the lower optical cutoff wavelength was identified to be 321 nm. The spectral study of photoluminescence was carried out in the range of 300-600 nm by which the band gap energy was calculated to be about 3.8 eV (at 373 nm) indicating that B35D has a violet fluorescence spectrum. The thermal stability and melting point of the title crystal have been investigated through Thermo gravimetric and differential thermal analysis (TG-DTA) such that the thermal stability of the crystal was found to be 95.6 °C. The Nd: YAG Q-switched laser was employed so as to obtain the laser-induced surface damage threshold of the specimen which was estimated to be 3.1 GW/cm². The Vickers microhardness test was implemented in order to arrive at the mechanical strength of the crystal. The performed non-linear optical study could reveal that the second-order harmonic generation (SHG) efficiency of B35D crystal is 2.16 times higher than KDP. So that B35D crystals are among the class of NLO materials.</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":"135898014","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":"Design and Synthesis of Some New Quinoxaline-1,2,4-Oxadiazole-Amide Conjugates as EGFR Targeting Agents and ADMET Studies","authors":"","doi":"10.1080/10406638.2023.2265027","DOIUrl":"10.1080/10406638.2023.2265027","url":null,"abstract":"<div><div>The synthesis of some new quinoxaline-1,2,4-oxadiazole-amide conjugates (<strong>6a–n</strong>) was described, and their structures were determined using ¹HNMR, ¹³CNMR, and mass spectral analysis. The <em>in vitro</em> anti-cancer activity of the compounds (<strong>6a–n</strong>) against three human cancer cell lines such as MCF-7 (breast), HepG2 (lung), and DU-145 (prostate) revealed that the compounds <strong>6d</strong>, <strong>6e</strong>, and <strong>6f</strong> exhibited promising activity against three cancer cell lines. Predominantly, compound <strong>6f</strong> demonstrated greater activity than the standard drug Etoposide on MCF-7, HepG2, and DU-145 with IC₅₀ values of 0.82 ± 0.01, 1.30 ± 0.02, and 2.12 ± 0.04 µM, respectively. Furthermore, the compounds <strong>6e</strong> and <strong>6f</strong> displayed promising inhibitory activity over the tyrosine kinase EGFR when compared with the standard Erlotinib. Molecular docking studies carried out on three potent compounds (<strong>6d</strong>, <strong>6e</strong>, and <strong>6f)</strong> on the EGFR receptor recommended that the compound <strong>6f</strong> strongly binds to protein EGFR (pdbid: 4HJO). In addition, the <em>in silico</em> pharmacokinetic profile was also achieved for the three potent compounds <strong>6d</strong>, <strong>6e</strong>, and <strong>6f</strong> using SWISS/ADME and pk CSM. Results showed that the compounds <strong>6d</strong>, <strong>6e</strong>, and <strong>6f</strong> followed the Lipinski rule, Veber rule, Egan rule, Ghose rule, and Muegge rule without any deviation.</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":"135095579","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":"Novel 1,2,4-triazolethiol–thiophen Hybrids: Facile Synthesis, Characterization, ADMET Prediction and Molecular Docking","authors":"","doi":"10.1080/10406638.2023.2264448","DOIUrl":"10.1080/10406638.2023.2264448","url":null,"abstract":"<div><div>In the present contribution, novel 1,2,4-triazolethiol–thiophene hybrids, namely 4-ethyl-5-(thiophen-2-yl)-4<em>H</em>-1,2,4-triazole-3-thiol (<strong>1</strong>) and 4-phenyl-5-(thiophen-2-yl)-4<em>H</em>-1,2,4-triazole-3-thiol (<strong>2</strong>), which were readily fabricated from addition of isothiocyanatoethane or isothiocyanatobenzene, respectively, to thiophene-2-carbohydrazide followed by addition a KOH solution to provoke the cyclization to the 1,2,4-triazole ring. The formation of compounds <strong>1</strong> and <strong>2</strong> was firmly confirmed by the means of elemental analysis, IR, ¹H and ¹³C{¹H} NMR spectroscopy. The DFT-based computations in gas phase were additionally applied to shed light on the structure and electronic features of the title compounds. Theoretical calculations revealed that for both molecules their corresponding thione derivatives, namely 4-ethyl-5-(thiophen-2-yl)-2,4-dihydro-3<em>H</em>-1,2,4-triazole-3-thione (<strong>1'</strong>) and 4-phenyl-5-(thiophen-2-yl)-2,4-dihydro-3<em>H</em>-1,2,4-triazole-3-thione (<strong>2'</strong>), are 15.00 and 11.96 kcal/mol, respectively, more energetically favorable in gas phase. However, a comparison of the experimental and calculated IR and NMR spectra testify to the thiol tautomers of compounds <strong>1</strong> and <strong>2</strong> for both compounds in solid state and in DMSO-<em>d</em>₆. The chemical activity of <strong>1</strong> and <strong>2</strong> was estimated by reactivity descriptors and MEP surface. ADMET properties of the reported compounds were predicted in silico using online services. Potential inhibition of a series of the tick-borne encephalitis (TBE) proteins by compounds <strong>1</strong> and <strong>2</strong> was studied using molecular docking, which, in turn, allowed to reveal the ligand efficiency scores for the resulting protein–ligand complexes. It was established that compound <strong>1</strong> exhibits the best activity against the tick-borne encephalitis virus Serine protease NS3, while compound <strong>2</strong> is preferable for the RNA-stimulated ATPase activity of tick-borne encephalitis virus helicase.</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":"135094580","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, X-Ray, Spectral Characterization, DFT, and Molecular Docking Calculations of 2-(5-Nitro-1-H-Indazol-1-yl) Acetic Acid","authors":"","doi":"10.1080/10406638.2023.2264453","DOIUrl":"10.1080/10406638.2023.2264453","url":null,"abstract":"<div><div>In this work, theoretical and experimental studies of a new Indazole derivative named 2-(5-nitro-1-<em>H</em>-indazol-1-yl) acetic acid (<strong>3</strong>), including the synthesis and characterization by ¹H and ¹³C-NMR, FT-IR, UV spectroscopies are reported together with its X-ray crystal structure. The compound crystallizes in the monoclinic crystal system of <em>P21/c</em> space group and unit cell constants: <em>a</em> = 7.8541(10) Å, <em>b</em> = 7.9274(11) Å, <em>c</em> = 15.877(2) Å, <em>β</em> = 101.149(5)°. In the crystal, O–H···N and C–H···O hydrogen bonds form a 3-D network structure containing small channels running parallel to the <em>b</em>-axis. B3LYP/6-311++G** calculations in the gas phase and ethanol solution suggest the existence of C1 and C2 conformers where the structure of C1 in both media is in agreement with that observed by X-ray diffraction. Probably, the high values observed in the dipole moments of C1 justify its presence in gas and solution phases. The stabilities of both forms were justified by NBO and AIM calculations where C1 is more stable than C2. C1 shows a higher solvation energy, dipole moment, and higher hydration than C2 while the frontier orbitals suggest a higher reactivity of C1 over C2. Force fields and complete vibrational assignments were performed for the C1 conformer because it was detected in the solid phase. Scaled force constants for both forms are also reported. Calculated chemical shifts for (<strong>3</strong>) are consistent with the experimental ¹H and ¹³C-NMR spectra in the DMSO-d₆ solution. The anti-COVID activity of <strong>3</strong> is investigated by its molecular docking into the binding site of SARS CoV-2 3CLpro (3 C-like protease). It shows a moderate binding affinity into the binding site of 3 C-like protease with a maximum binding energy of −5.57 kcal mol⁻¹.</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":"135094627","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":"In2O3 Nanoparticles: An Ecofriendly and Reusable Nano-Catalyst for Green Synthesis of 1,8-dioxo-octa-hydro Xanthene Derivatives","authors":"","doi":"10.1080/10406638.2023.2264446","DOIUrl":"10.1080/10406638.2023.2264446","url":null,"abstract":"<div><div>A novel, singular, and reusable In₂O₃ nanocatalyst was synthesized in the laboratory using a hydrothermal process. The In₂O₃ catalyst was characterized <em>via</em> specific strategies like Fourier transform infrared (FT-IR) was used to study the functional groups present in the In₂O₃ catalyst. Energy-dispersive X-ray spectroscopy (EDS) was used to analyze the elemental composition of the catalyst. A scanning electron microscope (SEM) was used to observe the morphology of the catalyst at a microscale level. X-ray diffraction pattern (XRD) was used to determine the crystal structure of the catalyst, and data analysis confirmed the formation of the crystalline phase of the In₂O₃ catalyst. The synthesized In₂O₃ catalyst was used for the synthesis of 1,8-dioxo-octa-hydro xanthene derivatives with 94% yield within 15 min of workup, this makes it a cost-effective and sustainable option for future synthesis reactions. Overall, the synthesis of this novel In₂O₃ nanocatalyst and its successful application in the synthesis of 1,8-dioxo-octa-hydro xanthene derivatives highlights the potential of green chemistry approaches in developing efficient and environmentally friendly chemical processes.</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":"135095582","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":"An Efficient Synthesis of 1, 3-Oxazine Derivatives Catalyzed under Ceric Ammonium Nitrate in an Aqueous Medium at Ambient Temperature","authors":"","doi":"10.1080/10406638.2023.2259569","DOIUrl":"10.1080/10406638.2023.2259569","url":null,"abstract":"<div><div>We report that ceric ammonium nitrate mediated the synthesis of 1, 3-oxazine derivatives under the green method. In the reaction, 20 mol% catalysts are sufficient for the complete conversion of the reaction. The condensation reaction of β-naphthol with formaldehyde and primary amines those containing electron-donating as well as electron-withdrawing substituents under the aqueous reaction condition at ambient temperature in the presence of ceric ammonium nitrate has been developed as an efficient and eco-friendly precursor for the determination of 1, 3-oxazine derivatives. This approach has numerous benefits beyond conventional systems, notably ease of use, expense, reusability of the catalyst, and faster reaction times.</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":"135059807","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 of 4-Azaindole-Thiazolidine-2,4-Dione Coupled 1,2,3-Triazoles as EGFR Directing Anticancer Agents","authors":"","doi":"10.1080/10406638.2023.2259563","DOIUrl":"10.1080/10406638.2023.2259563","url":null,"abstract":"<div><div>Herein, we synthesized some new 4-azaindole-thiazolidine-2,4-dione-1,2,3-triazole hybrids (<strong>6a-6n</strong>) <em>via</em> Knoevenagel condensation and copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) as key approaches. These hybrids were then screened for their <em>in vitro</em> anticancer activity against three human cancer cell lines like MCF-7 (breast), A549 (lung) and HepG2 (hepatocellular) using erlotinib as standard drug. Out of all, compounds <strong>6a</strong>, <strong>6k</strong> and <strong>6m</strong> were found to be more active against all cell lines with IC₅₀ values &lt;18 µM. As well, compounds <strong>6a</strong> (IC₅₀ = 0.40 µΜ), <strong>6k</strong> (IC₅₀ = 0.29 µΜ) and <strong>6m</strong> (IC₅₀ = 0.18 µΜ) showed higher potency ininhibiting tyrosine kinase EGFR than the erlotinib (IC₅₀ = 0.41 µΜ). Further, molecular dockingof compounds <strong>6a</strong>, <strong>6k</strong> and <strong>6 m</strong> on EGFR protein revealed that they have good binding energies with the target protein (−9.96 kcal/mol, −9.92 kcal/mol and −10.37 kcal/mol respectively) which were found to be supportive with the corresponding <em>in vitro</em> activities data.</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":"136136691","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 of Functionalized Isoxazolines as New Acetylcholinesterase and Tyrosinase Inhibitors and Antioxidant Agents","authors":"","doi":"10.1080/10406638.2023.2264449","DOIUrl":"10.1080/10406638.2023.2264449","url":null,"abstract":"<div><div>In the search for new leads capable of interacting with multiple targets involved in NDD pathogenesis, a series of pyrazine-linked isoxazoline scaffolds were designed, synthesized and evaluated for their acetylcholinesterase and tyrosinase inhibitory potency and antioxidant activity. Isoxazolines 4a, 4d and 4h exhibited better molecular interaction with cholinesterases, tyrosinases and peroxiredoxin enzymes. Isoxazolines 4a, 4d and 4h interacted with acetylcholinesterase with the highest docking score of −9.083, −8.68 and −7.87 kcal/mol, respectively. Compound 4h ranked top when interacting with butyrylcholinesterase with a docking score of −7.926 kcal/mol, followed by 4a (−6.327 kcal/mol). 4a exhibited a robust interaction with 1HD2 with a docking score of −3.103 kcal/mol followed by 4d and 4h. 4a, 4d and 4h exhibited better docking scores of −5.47 kcal/mol, −4.63 kcal/mol and −5.157 kcal/mol with the enzyme tyrosinase. Based on the <em>in-silico</em> data, we have proceeded further to synthesis and <em>in-vitro</em> studies. Chalcones were synthesized by the Claisen-Schmidt reaction, which was cyclised to isoxazolines by the cycloaddition of hydroxylamine HCl. FTIR, ¹HNMR, ¹³CNMR, and mass spectral studies further characterized the compounds. The prediction of pharmacokinetic parameters also supports the study, and all the compounds passed the screening. <em>In-vitro</em> studies were performed to evaluate acetylcholinesterase and tyrosinase inhibition. Compound 4h displayed excellent action against acetylcholinesterases and tyrosinase enzymes. Hydrogen peroxide assay determined the antioxidant effect, which found that 4h and 4d compounds exhibited higher strength as peroxide scavengers. Thus, the study shows that pyrazine-based isoxazolines with electron-withdrawing groups can be used as leads to develop a drug of choice for NDD, as it has excellent acetylcholinesterase and tyrosinase inhibitory action and tremendous peroxide scavenging effect.</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":"136210935","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":"Insight into the Binding Interaction Mechanism of the Ligand M1069 with Human Serum Albumin and A2A Adenosine Receptor—A Biophysical Approach","authors":"Shajith Ahamed Azees, Rupavarshini Manoharan, Navaneeth Alanthata Govindan, Bernet Shano Leon, Karthikeyan Subramani","doi":"10.1080/10406638.2024.2399536","DOIUrl":"https://doi.org/10.1080/10406638.2024.2399536","url":null,"abstract":"The study focuses on M1069, a promising drug for solid tumors functioning as an A2A adenosine receptor antagonist. Herein, we investigate the binding mechanism of the drug molecule M1069 by employi...","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":null,"pages":null},"PeriodicalIF":2.4,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142252796","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}