Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2265026
We synthesized a new series of coumarin-piperazine 1,2,3-triazole hybrids (7a–7n) and screened for their in vitro anti-breast cancer activity against MCF-7, MDA-MB-468, and MDA-MB-231 cancer cell lines. The results revealed that compound 7f showed superior activity against all cell lines than the standard drug 5-fluorouracil. As well, compounds 7e, 7h, and 7k showed greater activity against MCF-7 than the positive control. Furthermore, 7f and 7h showed higher potency in inhibiting tyrosine kinase epidermal growth factor receptor (EGFR) than the standard drug erlotinib. Finally, in silico molecular docking studies on EGFR (PDB ID-4HJO) revealed that compounds 7e, 7f, 7h, and 7k possess good binding energies and inhibition constants as compared to erlotinib.
{"title":"Coumarin-Piperazine Tethered 1,2,3-Triazoles: EGFR Targeting Anti-Breast Cancer Evaluation and Molecular Docking Studies","authors":"","doi":"10.1080/10406638.2023.2265026","DOIUrl":"10.1080/10406638.2023.2265026","url":null,"abstract":"<div><div>We synthesized a new series of coumarin-piperazine 1,2,3-triazole hybrids (<strong>7a–7n</strong>) and screened for their <em>in vitro</em> anti-breast cancer activity against MCF-7, MDA-MB-468, and MDA-MB-231 cancer cell lines. The results revealed that compound <strong>7f</strong> showed superior activity against all cell lines than the standard drug 5-fluorouracil. As well, compounds <strong>7e</strong>, <strong>7h</strong>, and <strong>7k</strong> showed greater activity against MCF-7 than the positive control. Furthermore, <strong>7f</strong> and <strong>7h</strong> showed higher potency in inhibiting tyrosine kinase epidermal growth factor receptor (EGFR) than the standard drug erlotinib. Finally, <em>in silico</em> molecular docking studies on EGFR (PDB ID-4HJO) revealed that compounds <strong>7e</strong>, <strong>7f</strong>, <strong>7h</strong>, and <strong>7k</strong> possess good binding energies and inhibition constants as compared to erlotinib.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 8","pages":"Pages 5487-5503"},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135729059","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 : 2024-09-13DOI: 10.1080/10406638.2023.2266170
Topological indices have gained significant attention in the field of chemical graph theory. These indices offer quantitative measures that accurately represent the topology of molecular graphs, which are used to model chemical compounds. Generally, their physical properties are closely linked to the geometric structures of these compounds. In this paper, we introduce a new family of phenylene-quadrilateral networks that exhibit unique features. These studied topological structures can be seen as generalizations of the phenylenes. To analyze the generalized phenylene-quadrilateral networks, we propose a recursive method for calculating their Kirchhoff index and the number of spanning trees. This method is based on the relationship between the coefficients and roots of the characteristic polynomial.
{"title":"Laplacian Spectrum of Linear Generalized Phenylene-Quadrilateral Networks and Its Applications","authors":"","doi":"10.1080/10406638.2023.2266170","DOIUrl":"10.1080/10406638.2023.2266170","url":null,"abstract":"<div><div>Topological indices have gained significant attention in the field of chemical graph theory. These indices offer quantitative measures that accurately represent the topology of molecular graphs, which are used to model chemical compounds. Generally, their physical properties are closely linked to the geometric structures of these compounds. In this paper, we introduce a new family of phenylene-quadrilateral networks that exhibit unique features. These studied topological structures can be seen as generalizations of the phenylenes. To analyze the generalized phenylene-quadrilateral networks, we propose a recursive method for calculating their Kirchhoff index and the number of spanning trees. This method is based on the relationship between the coefficients and roots of the characteristic polynomial.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 8","pages":"Pages 5609-5623"},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136097730","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 : 2024-09-13DOI: 10.1080/10406638.2023.2259564
4-Arylideneisoxazol-5(4H)-ones were obtained via a simple and efficient one-pot, three-component cyclocondensation of diverse aldehydes with hydroxylamine hydrochloride and β-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(4H)-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.
{"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 (SiO<sub>2</sub> 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 SiO<sub>2</sub> 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":"44 8","pages":"Pages 5022-5037"},"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}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2265024
We herein report the synthesis, spectral analysis, DFT calculations, in vitro and in silico biological activities of novel N'-((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 via 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 Mycobacterium tuberculosis. In the antioxidant activity, the Cu(II) complex showed excellent activity as compared to standard drugs and in silico docking studies were carried out against Cytochrome c Peroxidase (PDB ID: 2X08).
{"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, <sup>1</sup>H 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<sup>++</sup> (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<sup>−1</sup>) may be considered a promising antibacterial agent, and Ni(II) and Zn(II) complexes (MIC 25 µg mL<sup>−1</sup>) as promising antifungal agent. Also, synthesized Ni(II) and Zn(II) metal complexes (MIC 3.125 µg mL<sup>−1</sup>) 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":"44 8","pages":"Pages 5439-5459"},"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}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2266091
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 (E)-2-(2-(3,4-dihydronaphthalen-1(2H)-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.
{"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":"44 8","pages":"Pages 5530-5552"},"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}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2266093
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(α 0), first-hyperpolarizability (β), particularly ASH3, with the highest α 0 and β 0 computed to be 520.44 a.u. and 26166.79 a.u., respectively. Additionally, frequency-dependent hyperpolarizability SHG β(−2ω,ω,ω) and EOPE β(−ω,ω,0) calculations for commonly used lasers were performed at 1907.21, 532, and 1064 nm. ASH3 with terthiophene linker exhibits a striking EOPE β(−ω,ω,0) and SHG β(−2ω,ω,ω) 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.
{"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 × 10<sup>4</sup> a.u. and 3.80 × 10<sup>4</sup> 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":"44 8","pages":"Pages 5553-5583"},"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}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2261596
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.
{"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":"44 8","pages":"Pages 5218-5236"},"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}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2265022
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) (4a-r) 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.
{"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":"44 8","pages":"Pages 5412-5423"},"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}
Pub Date : 2024-09-13DOI: 10.1080/10406638.2023.2264452
In this study, a new deep eutectic mixture (DEM) was prepared from D-fructose, L-arginine, and urea and characterized by Fourier transform infrared (FT-IR), refractive index measurement, and thermogravimetric analysis (TGA). In continue this mixture was used as a green catalyst to promote the synthesis of three important derivatives of heterocyclic compounds. The highlights of this work include some notable advantages such as ease of the preparation and simple catalytic process, low cost, green reaction conditions, biodegradability of the catalyst, short reaction times, high yields of the products and simple work-up. Also, the catalyst could be recovered easily and reused up to several times without significant loss of catalytic activity.
{"title":"Use of a New Natural Deep Eutectic Mixture for the Acceleration of Some of the Important Multi-Component Reactions","authors":"","doi":"10.1080/10406638.2023.2264452","DOIUrl":"10.1080/10406638.2023.2264452","url":null,"abstract":"<div><div>In this study, a new deep eutectic mixture (DEM) was prepared from <em>D</em>-fructose, <em>L</em>-arginine, and urea and characterized by Fourier transform infrared (FT-IR), refractive index measurement, and thermogravimetric analysis (TGA). In continue this mixture was used as a green catalyst to promote the synthesis of three important derivatives of heterocyclic compounds. The highlights of this work include some notable advantages such as ease of the preparation and simple catalytic process, low cost, green reaction conditions, biodegradability of the catalyst, short reaction times, high yields of the products and simple work-up. Also, the catalyst could be recovered easily and reused up to several times without significant loss of catalytic activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 8","pages":"Pages 5362-5379"},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135093988","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 : 2024-09-13DOI: 10.1080/10406638.2023.2264454
The DMSO/I2 mediated cyclization reaction of (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one afforded the 2-(3,4-dimethoxyphenyl)-4H-chromen-4-one (DMPC). DMPC was characterized by FT-IR, 1H NMR, 13C NMR and HRMS techniques. DMPC was screened for their in vitro antibacterial activity against four bacterial strains namely E. coli, B. subtilis, S. aureus, and Streptococcus spp. and antifungal activity against R. oryzae, P. chrysogenum, A. niger, and C. albicans fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal properties. DMPC possesed potent antibacterial activity against Streptococcus spp. while the powerful antifungal action was found against P. chrysogenum. Besides % free radical scavenging activity was accessed using DPPH and OH assays. DMPC was found to be more active DPPH radical scavenger than OH radical. Theoretical investigation of DMPC was carried out by density functional theory (DFT) method at the B3LYP/6-311++G(d,p) level of theory. Computational investigation of molecular structure, MESP, and HOMO–LUMO was performed to study DMPC. The calculated energy gap of FMOs was found to be 4.25 eV for DMPC. In the MESP plot, the most electronegative potential region found around the oxygen atom. The theoretical and experimental NMR was correlated and correct NMR assignments have been made. Based on the physicochemical features, lipophilicity, water solubility, pharmacokinetic characteristics, and drug similarity matching investigations, the DMPC was revealed to have favorable biological qualities.
{"title":"Synthesis, Computational, Antimicrobial, Antioxidant, and ADME Study of 2-(3,4-Dimethoxyphenyl)-4H-Chromen-4-One","authors":"","doi":"10.1080/10406638.2023.2264454","DOIUrl":"10.1080/10406638.2023.2264454","url":null,"abstract":"<div><div>The DMSO/I<sub>2</sub> mediated cyclization reaction of (<em>E</em>)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one afforded the 2-(3,4-dimethoxyphenyl)-4<em>H</em>-chromen-4-one (DMPC). DMPC was characterized by FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS techniques. DMPC was screened for their <em>in vitro</em> antibacterial activity against four bacterial strains namely <em>E. coli</em>, <em>B. subtilis</em>, <em>S. aureus</em>, and <em>Streptococcus spp</em>. and antifungal activity against <em>R. oryzae</em>, <em>P. chrysogenum</em>, <em>A. niger</em>, and <em>C. albicans</em> fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal properties. DMPC possesed potent antibacterial activity against <em>Streptococcus spp</em>. while the powerful antifungal action was found against <em>P. chrysogenum.</em> Besides % free radical scavenging activity was accessed using DPPH and OH assays. DMPC was found to be more active DPPH radical scavenger than OH radical. Theoretical investigation of DMPC was carried out by density functional theory (DFT) method at the B3LYP/6-311++G(d,p) level of theory. Computational investigation of molecular structure, MESP, and HOMO–LUMO was performed to study DMPC. The calculated energy gap of FMOs was found to be 4.25 eV for DMPC. In the MESP plot, the most electronegative potential region found around the oxygen atom. The theoretical and experimental NMR was correlated and correct NMR assignments have been made. Based on the physicochemical features, lipophilicity, water solubility, pharmacokinetic characteristics, and drug similarity matching investigations, the DMPC was revealed to have favorable biological qualities.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"44 8","pages":"Pages 5397-5411"},"PeriodicalIF":2.4,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135094572","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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