Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140786
Letícia D. Costa , Samuel Guieu , Maria Amparo F. Faustino , Augusto C. Tomé
The functionalization of halogenated thiazolo[5,4-c]isoquinolines (TzIQ) through the Suzuki–Miyaura reaction with arylboronic acids is reported here for the first time. Three TzIQ derivatives bearing only chlorine atoms or chlorine and bromine atoms were used in this work. The results unequivocally confirm the impact of different halogen atoms, and their positions on the TzIQ core, on the outcome of these reactions. Excellent chemoselectivity was observed for the TzIQ bearing chlorine and bromine atoms. The new TzIQ derivatives were fully characterized by NMR and MS techniques and the structure of the TzIQ 9b was also confirmed by single-crystal X-ray diffraction. The absorption and emissive properties of the new compounds indicate that some of them may be useful in applications requiring strong luminescence and large Stokes shifts.
{"title":"Functionalization of thiazolo[5,4-c]isoquinolines through Suzuki–Miyaura coupling","authors":"Letícia D. Costa , Samuel Guieu , Maria Amparo F. Faustino , Augusto C. Tomé","doi":"10.1016/j.molstruc.2024.140786","DOIUrl":"10.1016/j.molstruc.2024.140786","url":null,"abstract":"<div><div>The functionalization of halogenated thiazolo[5,4-<em>c</em>]isoquinolines (TzIQ) through the Suzuki–Miyaura reaction with arylboronic acids is reported here for the first time. Three TzIQ derivatives bearing only chlorine atoms or chlorine and bromine atoms were used in this work. The results unequivocally confirm the impact of different halogen atoms, and their positions on the TzIQ core, on the outcome of these reactions. Excellent chemoselectivity was observed for the TzIQ bearing chlorine and bromine atoms. The new TzIQ derivatives were fully characterized by NMR and MS techniques and the structure of the TzIQ <strong>9b</strong> was also confirmed by single-crystal X-ray diffraction. The absorption and emissive properties of the new compounds indicate that some of them may be useful in applications requiring strong luminescence and large Stokes shifts.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140786"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720077","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Synthesis of new ferrocenylated benzimidazoles containing organochalcogen donor (Se and Te) atoms in the pendant arm, their corresponding ferrocenylated-NHCs salts and their thione and selenone derivatives have been described. All these compounds were characterized by Infrared (IR), multinuclear (1H, 13C, 77Se and 125Te) 1D and 2D NMR spectroscopy and mass spectrometry. The molecular structures of five compounds, viz. 1-(1-(ferrocenylselenyl)methyl)-benzimidazole (1), 1-(2-(ferrocenylselenyl)ethyl)-benzimidazole (3), 1-(2-(ferrocenyltelluro)ethyl)-benzimidazole (4), 3-ferrocenyl methyl-1-(2-(ferrocenylselenyl)ethyl)benzimidazolium iodide (8) 3-methyl-1-(2-(ferrocenylselenyl)ethyl)-benzimidazolin-2-selenone (11) were determined by X-ray crystallography. In these compounds, multiple intermolecular hydrogen bonding interactions, CH⋯N, CH⋯C, CH⋯S, CH⋯Se, CH⋯I, CH⋯O, and OH⋯I contribute to the formation of supramolecular structures. Cyclic voltammetric (CV) and thermogravimetric (TGA) studies of these ferrocenyl chalcogenated benzimidazole derivatives have also been carried out. The cyclic voltammogram for all the compounds (1-7) shows one well-defined ferrocene-based wave at a higher positive potential while in the selenated benzimidazoles (1) and (3) and their benzimidazolium salts (5) and (6) present another irreversible single-electron redox wave. The TGA curves of chalcogenated benzimidazolium salts show three steps of decomposition for compounds (6) and (7), and four steps of decomposition for compound (8). The antioxidant activity of benzimidazole precursors (1-4) and benzimidazolium salts (5-7) have been evaluated by conducting a thiobarbituric acid reactive substance (TBARS) assay. The IC50 value of all the compounds has been determined. The toxicity assay of all these compounds against Artemia Salina model at three different concentrations (1, 10 and 100 μM) was also studied.
{"title":"New ferrocenyl chalcogenated (Se, Te) benzimidazoles, benzimidazolium salts and chalcogenones: Structure, electrochemistry, thermal investigation and antioxidant activity","authors":"Rodary González , Pankaj Sharma , Claudia P. Villamizar C․ , Bertin Anzaldo , Dorancelly Fernandez , Guadalupe Hernandez , Antonio Nieto Camacho , Arun Kumar","doi":"10.1016/j.molstruc.2024.140735","DOIUrl":"10.1016/j.molstruc.2024.140735","url":null,"abstract":"<div><div>Synthesis of new ferrocenylated benzimidazoles containing organochalcogen donor (Se and Te) atoms in the pendant arm, their corresponding ferrocenylated-NHCs salts and their thione and selenone derivatives have been described. All these compounds were characterized by Infrared (IR), multinuclear (<sup>1</sup>H, <sup>13</sup>C, <sup>77</sup>Se and <sup>125</sup>Te) 1D and 2D NMR spectroscopy and mass spectrometry. The molecular structures of five compounds, <em>viz. 1-(1-(ferrocenylselenyl)methyl)-benzimidazole</em> (<strong>1</strong>), <em>1-(2-(ferrocenylselenyl)ethyl)-benzimidazole</em> (<strong>3</strong>), <em>1-(2-(ferrocenyltelluro)ethyl)-benzimidazole</em> (<strong>4</strong>), <em>3-ferrocenyl methyl-1-(2-(ferrocenylselenyl)ethyl)benzimidazolium iodide</em> (<strong>8</strong>) <em>3-methyl-1-(2-(ferrocenylselenyl)ethyl)-benzimidazolin-2-selenone</em> (<strong>11</strong>) were determined by X-ray crystallography. In these compounds, multiple intermolecular hydrogen bonding interactions, CH⋯N, CH⋯C, CH⋯S, CH⋯Se, CH⋯I, CH⋯O, and OH⋯I contribute to the formation of supramolecular structures. Cyclic voltammetric (CV) and thermogravimetric (TGA) studies of these ferrocenyl chalcogenated benzimidazole derivatives have also been carried out. The cyclic voltammogram for all the compounds (<strong>1-7</strong>) shows one well-defined ferrocene-based wave at a higher positive potential while in the selenated benzimidazoles (<strong>1</strong>) and (<strong>3</strong>) and their benzimidazolium salts (<strong>5</strong>) and (<strong>6</strong>) present another irreversible single-electron redox wave. The TGA curves of chalcogenated benzimidazolium salts show three steps of decomposition for compounds (<strong>6</strong>) and (<strong>7</strong>), and four steps of decomposition for compound (<strong>8</strong>). The antioxidant activity of benzimidazole precursors (<strong>1</strong>-<strong>4</strong>) and benzimidazolium salts (<strong>5</strong>-<strong>7</strong>) have been evaluated by conducting a thiobarbituric acid reactive substance (TBARS) assay. The IC<sub>50</sub> value of all the compounds has been determined. The toxicity assay of all these compounds against <em>Artemia Salina</em> model at three different concentrations (1, 10 and 100 μM) was also studied.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140735"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720067","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140732
Eman Y. Ahmed , Aya M. Serry , Hanan F. Aly , Ghadha I. Fouad , Omaima M. Abdelhafez
Two new series of coumarin hydrazide and chromone pyrazole derivatives were designed and synthesized to evaluate their in vitro and in vivo anti-Alzheimer activity. All the derivatives were tested for their ability to inhibit cholinesterases. Compound 14 displayed the highest in vitro inhibitory activity against acetylcholinesterase and butyrylcholinesterase with IC50 values of 3.31 µM and 1.60 µM, respectively. The in vivo study revealed the capability of the promising derivative to cause a decline in acetylcholinesterase levels, ameliorate the antioxidative activities of TAC and GSH, decrease the levels of MDA and NO, and down regulate that of MAP-TAU and APP. Moreover, the examination of the AD-brain regions treated with the synthetic compound 14 revealed an improvement of AD histological hallmarks. Molecular modeling of compound 14 demonstrated the interactions of the derivative with the key amino acids in AChE active site. A molecular dynamic simulation and an in silico pharmacokinetic study were conducted as well.
{"title":"Design, synthesis and molecular docking studies of tailored coumarin and chromone derivatives for use as anti-Alzheimer agents","authors":"Eman Y. Ahmed , Aya M. Serry , Hanan F. Aly , Ghadha I. Fouad , Omaima M. Abdelhafez","doi":"10.1016/j.molstruc.2024.140732","DOIUrl":"10.1016/j.molstruc.2024.140732","url":null,"abstract":"<div><div>Two new series of coumarin hydrazide and chromone pyrazole derivatives were designed and synthesized to evaluate their <em>in vitro</em> and <em>in vivo</em> anti-Alzheimer activity. All the derivatives were tested for their ability to inhibit cholinesterases. Compound <strong>14</strong> displayed the highest <em>in vitro</em> inhibitory activity against acetylcholinesterase and butyrylcholinesterase with IC<sub>50</sub> values of 3.31 µM and 1.60 µM, respectively. The <em>in vivo</em> study revealed the capability of the promising derivative to cause a decline in acetylcholinesterase levels, ameliorate the antioxidative activities of TAC and GSH, decrease the levels of MDA and NO, and down regulate that of MAP-TAU and APP. Moreover, the examination of the AD-brain regions treated with the synthetic compound <strong>14</strong> revealed an improvement of AD histological hallmarks. Molecular modeling of compound <strong>14</strong> demonstrated the interactions of the derivative with the key amino acids in AChE active site. A molecular dynamic simulation and an in silico pharmacokinetic study were conducted as well.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140732"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140775
Raúl Segovia-Pérez , Blanca M. Muñoz-Flores , José G. Alvarado-Rodríguez , Noemí Waksman , Verónica Rivas , Casiano del Angel-Mosqueda , C.C. Vidyasagar , Azael A. Cavazos-Jaramillo , Juan M. Alcocer-González , Nicolás Puentes-Díaz , Jorge Alí-Torres , Víctor M. Jiménez-Pérez
Using non-cytotoxic fluorescent materials for staining Bombyx mori silk fibroin holds great promise for tissue engineering and regenerative medicine, as it could be used as a scaffold and monitor for cell growth. Here, we report the microwave-assisted synthesis of two fluorescent Schiff bases in short reaction time and good yields. Detailed characterization of the synthesized compounds using NMR (1H, 13C NMR, and 2D NMR experiments), HRMS (DART+), UV/Vis, fluorescence spectroscopy, and X-ray diffraction studies. The Schiff base molecular structures showed a non-planar arrangement with the C2 point group. Both compounds showed low cytotoxicity on colon carcinoma cells (Caco2, ATCCHTB-37) at different concentrations (1 to 5 μg/mL). Notably, Schiff bases exhibit good fluorescent staining of Bombyx mori silk fibroin by the immersion method and were analyzed by confocal microscopy. The fluorescent staining ability of the Schiff bases toward the silk fibroin was explored by molecular docking, where two predominant binding sites were identified, and H-bonding and other polar interactions were found to stabilize the binding modes of the compounds. From the remarkable findings and to the best of our knowledge, this is the first report on Schiff bases as a fluorescent dye of this biomaterial.
使用无毒荧光材料染色蚕丝纤维素在组织工程和再生医学中大有可为，因为它可用作支架和细胞生长监测器。在此，我们报告了微波辅助合成两种荧光席夫碱的方法，反应时间短，产率高。利用核磁共振（1H、13C NMR 和 2D NMR 实验）、HRMS（DART+）、紫外/可见光谱、荧光光谱和 X 射线衍射研究对合成的化合物进行了详细表征。希夫碱分子结构显示出 C2 点基团的非平面排列。在不同浓度（1 至 5 μg/mL）下，这两种化合物对结肠癌细胞（Caco2、ATCCHTB-37）的细胞毒性都很低。值得注意的是，希夫碱通过浸泡法对蚕丝纤维素具有良好的荧光染色作用，并通过共聚焦显微镜进行了分析。通过分子对接研究了希夫碱对蚕丝纤维素的荧光染色能力，发现了两个主要的结合位点，并发现 H 键和其他极性相互作用稳定了化合物的结合模式。据我们所知，这是有关希夫碱作为这种生物材料的荧光染料的首次报道。
{"title":"Microwave-assisted synthesis, characterization and molecular docking of two C2-symmetric Schiff bases as fluorescent dye for silk fibroin","authors":"Raúl Segovia-Pérez , Blanca M. Muñoz-Flores , José G. Alvarado-Rodríguez , Noemí Waksman , Verónica Rivas , Casiano del Angel-Mosqueda , C.C. Vidyasagar , Azael A. Cavazos-Jaramillo , Juan M. Alcocer-González , Nicolás Puentes-Díaz , Jorge Alí-Torres , Víctor M. Jiménez-Pérez","doi":"10.1016/j.molstruc.2024.140775","DOIUrl":"10.1016/j.molstruc.2024.140775","url":null,"abstract":"<div><div>Using non-cytotoxic fluorescent materials for staining <em>Bombyx mori</em> silk fibroin holds great promise for tissue engineering and regenerative medicine, as it could be used as a scaffold and monitor for cell growth. Here, we report the microwave-assisted synthesis of two fluorescent Schiff bases in short reaction time and good yields. Detailed characterization of the synthesized compounds using NMR (<sup>1</sup>H, <sup>13</sup>C NMR, and 2D NMR experiments), HRMS (DART+), UV/Vis, fluorescence spectroscopy, and X-ray diffraction studies. The Schiff base molecular structures showed a non-planar arrangement with the <em>C</em><sub>2</sub> point group. Both compounds showed low cytotoxicity on colon carcinoma cells (Caco2, ATCC<img>HTB-37) at different concentrations (1 to 5 μg/mL). Notably, Schiff bases exhibit good fluorescent staining of <em>Bombyx mori</em> silk fibroin by the immersion method and were analyzed by confocal microscopy. The fluorescent staining ability of the Schiff bases toward the silk fibroin was explored by molecular docking, where two predominant binding sites were identified, and H-bonding and other polar interactions were found to stabilize the binding modes of the compounds. From the remarkable findings and to the best of our knowledge, this is the first report on Schiff bases as a fluorescent dye of this biomaterial.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140775"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720285","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140774
Meng Ye , Hongying Hou , Xianxi Liu , Zhaowei Sun , Xiaohua Yu , Ju Rong
With the development of the consumer society, low cost and high performance supercapacitors are being pursued. To realize the practical supercapacitors, developing the cheap and highly capacitive electrode is the most essential. However, it is a harsh challenge to achieve this target based on single-component electrode. Herein, a series of inexpensive ternary-metal-sulfides, 2MnS/Cu2S/xZnS/C (x = 0, 0.5, 1, 2, 3) are synthesized by hydrothermal reaction and the subsequent calcination with expired manganese/copper gluconates as the raw materials for the electrode in the pseudocapacitors. Furthermore, the effect of ZnS's content on the electrochemical properties of the ternary composites is also investigated. Specially, the optimal 2MnS/Cu2S/xZnS/C(x = 1) can output a specific capacitance of 1608 F/g at 1 A/g in the three-electrode system, while the 2MnS/Cu2S/xZnS/C||AC(x = 1) asymmetric supercapacitor can deliver a specific capacitance of 194 F/g at 1 A/g with the desirable energy density (800 W/kg) and power density (70.9 Wh/kg), higher than those of other samples. Especially, even after 2000 cycles at 5.0 A/g, the 2MnS/Cu2S/xZnS/C||AC(x = 1) asymmetric supercapacitor also delivers the reversible specific capacitance of 103 F/g with high capacitance retention of 97.0 %, indicating high cycling stability. The outstanding performances of the optimal 2MnS/Cu2S/xZnS/C(x = 1) may be attributed to the bridge-effect of ZnS component, which makes up for the low conductivity of MnS component and the low capacitance of Cu2S component, thus achieving the best synergistic effect of ternary metal sulfide 2MnS/Cu2S/xZnS/C(x = 1) .
{"title":"Ternary-metal-sulfide 2MnS/Cu2S/xZnS/C (x = 0, 0.5, 1, 2, 3) electrodes for high performance supercapacitors","authors":"Meng Ye , Hongying Hou , Xianxi Liu , Zhaowei Sun , Xiaohua Yu , Ju Rong","doi":"10.1016/j.molstruc.2024.140774","DOIUrl":"10.1016/j.molstruc.2024.140774","url":null,"abstract":"<div><div>With the development of the consumer society, low cost and high performance supercapacitors are being pursued. To realize the practical supercapacitors, developing the cheap and highly capacitive electrode is the most essential. However, it is a harsh challenge to achieve this target based on single-component electrode. Herein, a series of inexpensive ternary-metal-sulfides, 2MnS/Cu<sub>2</sub>S/<em>x</em>ZnS/C (<em>x</em> = 0, 0.5, 1, 2, 3) are synthesized by hydrothermal reaction and the subsequent calcination with expired manganese/copper gluconates as the raw materials for the electrode in the pseudocapacitors. Furthermore, the effect of ZnS's content on the electrochemical properties of the ternary composites is also investigated. Specially, the optimal 2MnS/Cu<sub>2</sub>S/xZnS/C(<em>x</em> = 1) can output a specific capacitance of 1608 F/g at 1 A/g in the three-electrode system, while the 2MnS/Cu<sub>2</sub>S/xZnS/C||AC(<em>x</em> = 1) asymmetric supercapacitor can deliver a specific capacitance of 194 F/g at 1 A/g with the desirable energy density (800 W/kg) and power density (70.9 Wh/kg), higher than those of other samples. Especially, even after 2000 cycles at 5.0 A/g, the 2MnS/Cu<sub>2</sub>S/xZnS/C||AC(<em>x</em> = 1) asymmetric supercapacitor also delivers the reversible specific capacitance of 103 F/g with high capacitance retention of 97.0 %, indicating high cycling stability. The outstanding performances of the optimal 2MnS/Cu<sub>2</sub>S/xZnS/C(<em>x</em> = 1) may be attributed to the bridge-effect of ZnS component, which makes up for the low conductivity of MnS component and the low capacitance of Cu<sub>2</sub>S component, thus achieving the best synergistic effect of ternary metal sulfide 2MnS/Cu<sub>2</sub>S/xZnS/C(<em>x</em> = 1) .</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140774"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720080","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140792
Dong-Mei Liu , Shao-Cong Zhan , Ren-Jie Fang , Jing Sun , Chao-Guo Yan
p-TsOH catalyzed [3+2] cycloaddition of 3-benzoylvinylindoles with 3-hydroxy-3-(indol-3-yl)indolin-2-ones in acetonitrile gave functionalized 3,4-dihydrospiro[cyclopenta[b]indole-1,3′-indolin]-2′-ones in good yields and with high diastereoselectivity. In the presence of FeCl3, the similar reaction of 3-benzoylvinylindoles with 3-hydroxy-3-(indol-3-yl)indolin-2-ones in toluene afforded dehydrogenated spiro[cyclopenta[b]indole-1,3′-indolin]-2′-ones in good yields. On the other hand, p-TsOH catalyzed [3+2] cycloaddition of 3-benzoylvinylindoles and 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones gave 3,4-dihydrospiro[cyclopenta[b]indole-1,2′-indene]-1′,3′-diones, which could be oxidized to dehydrogenated spiro[cyclopenta[b]indole-1,2′-indene]-1′,3′-diones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).
{"title":"Selective synthesis of dihydro- and dehydrogenated spirocyclopenta[b]indoles via acid-modulated [3+2] cycloaddition reaction","authors":"Dong-Mei Liu , Shao-Cong Zhan , Ren-Jie Fang , Jing Sun , Chao-Guo Yan","doi":"10.1016/j.molstruc.2024.140792","DOIUrl":"10.1016/j.molstruc.2024.140792","url":null,"abstract":"<div><div><em>p</em>-TsOH catalyzed [3+2] cycloaddition of 3-benzoylvinylindoles with 3-hydroxy-3-(indol-3-yl)indolin-2-ones in acetonitrile gave functionalized 3,4-dihydrospiro[cyclopenta[<em>b</em>]indole-1,3′-indolin]-2′-ones in good yields and with high diastereoselectivity. In the presence of FeCl<sub>3,</sub> the similar reaction of 3-benzoylvinylindoles with 3-hydroxy-3-(indol-3-yl)indolin-2-ones in toluene afforded dehydrogenated spiro[cyclopenta[<em>b</em>]indole-1,3′-indolin]-2′-ones in good yields. On the other hand, <em>p</em>-TsOH catalyzed [3+2] cycloaddition of 3-benzoylvinylindoles and 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones gave 3,4-dihydrospiro[cyclopenta[<em>b</em>]indole-1,2′-indene]-1′,3′-diones, which could be oxidized to dehydrogenated spiro[cyclopenta[<em>b</em>]indole-1,2′-indene]-1′,3′-diones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140792"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720949","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140790
Ibrahim M.Z. Fares , Mohamed A. Ragheb , Ismail A. Abdelhamid , Ahmed H.M. Elwahy
The research focused on studying how 7-hydroxy-4-methyl-2H-chromen-2-one can be used as a building material for new bis- and poly(coumarins) through alkylation with related bis- and poly(halo) compounds. Spectroscopic techniques confirmed the chemical compositions of these compounds. An experiment was conducted to assess the effectiveness of new coumarin derivatives in inhibiting the growth of various harmful bacterial strains in a controlled environment. Among the recently formed compounds, tris-coumarin 19 and bis-coumarin linked to thienothiophene core 26 demonstrated notable antibacterial effectiveness against the bacteria examined. Compounds 19 and 26 were evaluated for their interactions with CT-DNA using UV-Vis spectroscopy, resulting in a significant decrease in absorbance intensity with a slight shift towards longer wavelengths. Research using computer simulations of molecular docking indicates that compounds 19 and 26 can effectively attach to different target proteins such as DNA gyrase, dihydropteroate synthase, MurE ligase, and dihydrofolate reductase, achieving binding scores ranging from -9.76 to -6.68 kcal/mole. This indicates that our derivatives can prevent these proteins and display significant antibacterial characteristics. Additionally, assessments were done on compound 19 for drug-likeness and compound 26 for ADMET properties, indicating their potential as valuable candidates for further drug development.
{"title":"Synthesis, antimicrobial, DNA binding, and computational studies of some bis- and poly(4-methyl-2H-chromen-2-one) derivatives","authors":"Ibrahim M.Z. Fares , Mohamed A. Ragheb , Ismail A. Abdelhamid , Ahmed H.M. Elwahy","doi":"10.1016/j.molstruc.2024.140790","DOIUrl":"10.1016/j.molstruc.2024.140790","url":null,"abstract":"<div><div>The research focused on studying how 7-hydroxy-4-methyl-2<em>H</em>-chromen-2-one can be used as a building material for new bis- and poly(coumarins) through alkylation with related bis- and poly(halo) compounds. Spectroscopic techniques confirmed the chemical compositions of these compounds. An experiment was conducted to assess the effectiveness of new coumarin derivatives in inhibiting the growth of various harmful bacterial strains in a controlled environment. Among the recently formed compounds, tris-coumarin <strong>19</strong> and bis-coumarin linked to thienothiophene core <strong>26</strong> demonstrated notable antibacterial effectiveness against the bacteria examined. Compounds <strong>19</strong> and <strong>26</strong> were evaluated for their interactions with CT-DNA using UV-Vis spectroscopy, resulting in a significant decrease in absorbance intensity with a slight shift towards longer wavelengths. Research using computer simulations of molecular docking indicates that compounds <strong>19</strong> and <strong>26</strong> can effectively attach to different target proteins such as DNA gyrase, dihydropteroate synthase, MurE ligase, and dihydrofolate reductase, achieving binding scores ranging from -9.76 to -6.68 kcal/mole. This indicates that our derivatives can prevent these proteins and display significant antibacterial characteristics. Additionally, assessments were done on compound <strong>19</strong> for drug-likeness and compound <strong>26</strong> for ADMET properties, indicating their potential as valuable candidates for further drug development.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140790"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720081","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140788
Seyed Reza Barzegar Kiadehi, Hamid Golchoubian
A novel dinuclear copper(II) complex, [Cu₂L₂(μ-Cl)₂]Cl₂•4H₂O, was synthesized using a tetradentate hemilabile ligand, 3,3′-((pyridin-2-ylmethyl)azanediyl)dipropanamide (L). The complex was characterized by various spectroscopic techniques, including FT-IR, UV-Vis spectroscopy, elemental analysis, TG-DTA, and conductivity measurements. X-ray crystallography confirmed the formation of the binuclear complex, revealing a dicationic unit with distorted octahedral geometry at the copper centers, bridged by two chloride ions. The coordination environment around each copper ion includes two nitrogen and two oxygen donors from the ligand, along with the bridging chlorides. Notably, the complex exhibits significant chromotropism, including solvatochromism, halochromism, ionochromism, and thermochromism, which are attributed to the Jahn-Teller effect and the flexible coordination environment around the copper centers. Thermal analysis indicates the stability of the complex up to 118°C, with subsequent decomposition occurring in distinct stages. Hirshfeld surface analysis further elucidates the intermolecular interactions within the crystal lattice. Computational studies were conducted using Time Dependent Density Functional Theory (TD-DFT) to gain insights into the nature of the observed chromotropism. The computed absorption spectra closely matched the experimental data, validating the proposed electronic transitions responsible for the chromotropic behavior. The multifaceted chromotropic behavior of this complex highlights its potential applications in sensing technologies and smart materials. The study advances the understanding of chromotropism in metal complexes and provides insights into the design of responsive materials based on transition metal chemistry.
{"title":"A multichromotropic dinuclear copper(II) complex: Unveiling its structural and spectroscopic properties","authors":"Seyed Reza Barzegar Kiadehi, Hamid Golchoubian","doi":"10.1016/j.molstruc.2024.140788","DOIUrl":"10.1016/j.molstruc.2024.140788","url":null,"abstract":"<div><div>A novel dinuclear copper(II) complex, [Cu₂L₂(μ-Cl)₂]Cl₂•4H₂O, was synthesized using a tetradentate hemilabile ligand, 3,3′-((pyridin-2-ylmethyl)azanediyl)dipropanamide (L). The complex was characterized by various spectroscopic techniques, including FT-IR, UV-Vis spectroscopy, elemental analysis, TG-DTA, and conductivity measurements. X-ray crystallography confirmed the formation of the binuclear complex, revealing a dicationic unit with distorted octahedral geometry at the copper centers, bridged by two chloride ions. The coordination environment around each copper ion includes two nitrogen and two oxygen donors from the ligand, along with the bridging chlorides. Notably, the complex exhibits significant chromotropism, including solvatochromism, halochromism, ionochromism, and thermochromism, which are attributed to the Jahn-Teller effect and the flexible coordination environment around the copper centers. Thermal analysis indicates the stability of the complex up to 118°C, with subsequent decomposition occurring in distinct stages. Hirshfeld surface analysis further elucidates the intermolecular interactions within the crystal lattice. Computational studies were conducted using Time Dependent Density Functional Theory (TD-DFT) to gain insights into the nature of the observed chromotropism. The computed absorption spectra closely matched the experimental data, validating the proposed electronic transitions responsible for the chromotropic behavior. The multifaceted chromotropic behavior of this complex highlights its potential applications in sensing technologies and smart materials. The study advances the understanding of chromotropism in metal complexes and provides insights into the design of responsive materials based on transition metal chemistry.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140788"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720084","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140771
Yue Zhang , Can Wang , Yuan Zhou , Yun Yu , Wei Shu , Yunfeng Chen
Four triphenylethylene derivatives have been designed and synthesized in this work. Compared to traditional tetraphenylethene (TPE) compounds, it was found that the obtained compounds could exhibit potential isomerism in chemical and spatial structures due to their unique asymmetry, which revealed that the subtle structural changes directly influence the packing modes of the compounds in aggregated state, tuning their mechanochromic luminescence properties. Moreover, the emission wavelength of mono-substituted triphenylethylene derivatives showed a blue-shift trend when stimulated by external mechanical forces. After fuming or recrystallization, they can recover to long-wavelength emission. Among them, compound TTC-2 exhibited the most significant color changes and the largest wavelength variation.
{"title":"Tuning the reversible mechanochromic luminescence of triphenylethylenes by rational introduction of functionalized thiophenes substituents","authors":"Yue Zhang , Can Wang , Yuan Zhou , Yun Yu , Wei Shu , Yunfeng Chen","doi":"10.1016/j.molstruc.2024.140771","DOIUrl":"10.1016/j.molstruc.2024.140771","url":null,"abstract":"<div><div>Four triphenylethylene derivatives have been designed and synthesized in this work. Compared to traditional tetraphenylethene (TPE) compounds, it was found that the obtained compounds could exhibit potential isomerism in chemical and spatial structures due to their unique asymmetry, which revealed that the subtle structural changes directly influence the packing modes of the compounds in aggregated state, tuning their mechanochromic luminescence properties. Moreover, the emission wavelength of mono-substituted triphenylethylene derivatives showed a blue-shift trend when stimulated by external mechanical forces. After fuming or recrystallization, they can recover to long-wavelength emission. Among them, compound TTC-2 exhibited the most significant color changes and the largest wavelength variation.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1323 ","pages":"Article 140771"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720152","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-11-17DOI: 10.1016/j.molstruc.2024.140787
Adel Alhowyan , Wael A. Mahdi , Ahmad J. Obaidullah
We investigated the delivery of gingerol (GGL) loaded onto pristine and B-, Mg-, and Ga-doped aluminum nitride (Al12N12) fullerene-like cages in water, methanol, and dichloromethane phases using density functional theory (DFT) to explore its potential for cancer treatment. The chemisorption of GGL via hydroxyl and carbonyl groups on the Al12N12 surface resulted in an enhanced the dipole moment and binding energy (Ebin) in the water phase compared to methanol and dichloromethane phases at the CAM-B3LYP method. This adsorption process resulted in slight shifts in the electronic structure of all the complexes. Adsorption analysis revealed that the hydroxyl group of GGL, unlike its carbonyl group, exhibits strong interactions with the B atom in Al11BN12, the Mg atom in Al11MgN12, and the Ga atom in Al11GaN12 fullerene-like cages. The Al11MgN12 and Al11BN12 fullerene-like cages exhibit weaker binding energies compared to Al11GaN12, resulting in shorter desorption times. This facilitates the delivery of GGL and increases its dipole moment, thereby enhancing its solubility. Additionally, GGL loaded onto Al11MgN12 increases hardness, electronegativity, and electrophilicity while decreasing softness, indicating enhanced stability and interaction capabilities. Moreover, Al11MgN12 exhibits high sensitivity to GGL molecules as a biosensor, owing to significant shifts in its energy gap compared to Al11GaN12 and Al11BN12 cages. Theoretical infrared (IR) spectroscopy calculations indicate changes in vibration frequencies due to GGL adsorption onto fullerene-like cages. Overall, the findings suggest that GGL-loaded Al11MgN12 has promising potential for improving solubility and efficacy in drug delivery systems for biological applications.
{"title":"Single-metal doped Al12N12 fullerene-like cages as carriers for targeted gingerol delivery in various solvents","authors":"Adel Alhowyan , Wael A. Mahdi , Ahmad J. Obaidullah","doi":"10.1016/j.molstruc.2024.140787","DOIUrl":"10.1016/j.molstruc.2024.140787","url":null,"abstract":"<div><div>We investigated the delivery of gingerol (GGL) loaded onto pristine and B-, Mg-, and Ga-doped aluminum nitride (Al<sub>12</sub>N<sub>12</sub>) fullerene-like cages in water, methanol, and dichloromethane phases using density functional theory (DFT) to explore its potential for cancer treatment. The chemisorption of GGL via hydroxyl and carbonyl groups on the Al<sub>12</sub>N<sub>12</sub> surface resulted in an enhanced the dipole moment and binding energy (E<sub>bin</sub>) in the water phase compared to methanol and dichloromethane phases at the CAM-B3LYP method. This adsorption process resulted in slight shifts in the electronic structure of all the complexes. Adsorption analysis revealed that the hydroxyl group of GGL, unlike its carbonyl group, exhibits strong interactions with the B atom in Al<sub>11</sub>BN<sub>12</sub>, the Mg atom in Al<sub>11</sub>MgN<sub>12</sub>, and the Ga atom in Al<sub>11</sub>GaN<sub>12</sub> fullerene-like cages. The Al<sub>11</sub>MgN<sub>12</sub> and Al<sub>11</sub>BN<sub>12</sub> fullerene-like cages exhibit weaker binding energies compared to Al<sub>11</sub>GaN<sub>12</sub>, resulting in shorter desorption times. This facilitates the delivery of GGL and increases its dipole moment, thereby enhancing its solubility. Additionally, GGL loaded onto Al<sub>11</sub>MgN<sub>12</sub> increases hardness, electronegativity, and electrophilicity while decreasing softness, indicating enhanced stability and interaction capabilities. Moreover, Al<sub>11</sub>MgN<sub>12</sub> exhibits high sensitivity to GGL molecules as a biosensor, owing to significant shifts in its energy gap compared to Al<sub>11</sub>GaN<sub>12</sub> and Al<sub>11</sub>BN<sub>12</sub> cages. Theoretical infrared (IR) spectroscopy calculations indicate changes in vibration frequencies due to GGL adsorption onto fullerene-like cages. Overall, the findings suggest that GGL-loaded Al<sub>11</sub>MgN<sub>12</sub> has promising potential for improving solubility and efficacy in drug delivery systems for biological applications.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1324 ","pages":"Article 140787"},"PeriodicalIF":4.0,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号