Pub Date : 2025-05-04DOI: 10.1080/17415993.2025.2464799
Mostafa R. Abukhadra , Ahmed M. El-Sherbeeny , Mehdi Tlija , Li Shen
The widespread use of thiazole derivatives in medicinal and medical chemistry and the presence of the thiazole ring in the structure of critical biological molecules increased the popularity of these compounds among synthetic chemists. In this paper, we fabricated a nanomagnetic copper catalyst via the immobilization of CuCl2 on the surface of Fe3O4@SiO2-APA/OCA ligand by simple methods. We characterized its structure using spectroscopic techniques such as FT-IR, SEM, TEM, VSM, TGA, XRD, ICP-OES, EDX, and elemental mapping techniques. The Fe3O4@SiO2-APA/OCA-CuCl2 nanocomposite showed high catalytic activity in the preparation of 2,4-substituted thiazoles through multicomponent reactions of different phenylmethanamines, 2-phenylacetaldehyde derivatives and S8 (as sulfur source) under oxygen molecular and mild conditions. This method has several outstanding features, which can be mentioned as follows: performing the reaction in green solvent under mild conditions in less than four h, synthesis of thiazole products with very high yields, high activity of the Fe3O4@SiO2-APA/OCA-CuCl2 catalyst, simple separation of the nanomagnetic catalyst from the mixture using an external magnet, and the high reusability of the Fe3O4@SiO2-APA/OCA-CuCl2 catalyst.
{"title":"Fe3O4@SiO2-APA/OCA-Cucl2 nanocomposite: an efficient and reusable heterogenous catalyst for three-component synthesis of thiazole derivatives","authors":"Mostafa R. Abukhadra , Ahmed M. El-Sherbeeny , Mehdi Tlija , Li Shen","doi":"10.1080/17415993.2025.2464799","DOIUrl":"10.1080/17415993.2025.2464799","url":null,"abstract":"<div><div>The widespread use of thiazole derivatives in medicinal and medical chemistry and the presence of the thiazole ring in the structure of critical biological molecules increased the popularity of these compounds among synthetic chemists. In this paper, we fabricated a nanomagnetic copper catalyst via the immobilization of CuCl<sub>2</sub> on the surface of Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>-APA/OCA ligand by simple methods. We characterized its structure using spectroscopic techniques such as FT-IR, SEM, TEM, VSM, TGA, XRD, ICP-OES, EDX, and elemental mapping techniques. The Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>-APA/OCA-CuCl<sub>2</sub> nanocomposite showed high catalytic activity in the preparation of 2,4-substituted thiazoles through multicomponent reactions of different phenylmethanamines, 2-phenylacetaldehyde derivatives and S<sub>8</sub> (as sulfur source) under oxygen molecular and mild conditions. This method has several outstanding features, which can be mentioned as follows: performing the reaction in green solvent under mild conditions in less than four h, synthesis of thiazole products with very high yields, high activity of the Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>-APA/OCA-CuCl<sub>2</sub> catalyst, simple separation of the nanomagnetic catalyst from the mixture using an external magnet, and the high reusability of the Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>-APA/OCA-CuCl<sub>2</sub> catalyst.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 3","pages":"Pages 455-478"},"PeriodicalIF":2.1,"publicationDate":"2025-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144107192","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-04DOI: 10.1080/17415993.2025.2473740
Nadia Sebbar , Henning Bockhorn , Joseph W. Bozzelli , Dimosthenis Trimis
The reaction of disulfur (3S2) with oxygen 3S2 + 3O2 is an important reaction in sulfur combustion leading to different 1S2O2 isomers and subsequent intramolecular isomerization reactions. In this work reaction paths and products resulting from the reaction 3S2 + 3O2 are investigated computationally using four different quantum chemistry methods. The thermochemistry of the isomerization and dissociation reactions for species involved in this system is evaluated in detail and reported along with reaction paths and energy barriers. Enthalpies are calculated on CBS-QB3, G3B3, G4 levels of calculation and, whenever possible, on W1U levels. Entropy and heat capacity contributions versus temperature are determined from molecular structures, moments of inertia and vibrational frequencies. Importance of the reaction paths and kinetic parameters using bimolecular chemical activation analysis are estimated as function of temperature from the calculated thermochemical data. High pressure limit kinetic parameters are obtained from canonical transition state theory (TST) calculations. Results show that 1SS(=O)=O, 3SO, 1SO2 and 3S are the low energy products.
{"title":"Computational investigation of the isomers formed from the reaction S2 + O2","authors":"Nadia Sebbar , Henning Bockhorn , Joseph W. Bozzelli , Dimosthenis Trimis","doi":"10.1080/17415993.2025.2473740","DOIUrl":"10.1080/17415993.2025.2473740","url":null,"abstract":"<div><div>The reaction of disulfur (<sup>3</sup>S<sub>2</sub>) with oxygen <sup>3</sup>S<sub>2 </sub>+ <sup>3</sup>O<sub>2</sub> is an important reaction in sulfur combustion leading to different <sup>1</sup>S<sub>2</sub>O<sub>2</sub> isomers and subsequent intramolecular isomerization reactions. In this work reaction paths and products resulting from the reaction <sup>3</sup>S<sub>2</sub> + <sup>3</sup>O<sub>2</sub> are investigated computationally using four different quantum chemistry methods. The thermochemistry of the isomerization and dissociation reactions for species involved in this system is evaluated in detail and reported along with reaction paths and energy barriers. Enthalpies are calculated on CBS-QB3, G3B3, G4 levels of calculation and, whenever possible, on W1U levels. Entropy and heat capacity contributions versus temperature are determined from molecular structures, moments of inertia and vibrational frequencies. Importance of the reaction paths and kinetic parameters using bimolecular chemical activation analysis are estimated as function of temperature from the calculated thermochemical data. High pressure limit kinetic parameters are obtained from canonical transition state theory (TST) calculations. Results show that <sup>1</sup>SS(=O)=O, <sup>3</sup>SO, <sup>1</sup>SO<sub>2</sub> and <sup>3</sup>S are the low energy products.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 3","pages":"Pages 416-434"},"PeriodicalIF":2.1,"publicationDate":"2025-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144107190","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-04DOI: 10.1080/17415993.2025.2453751
Yongpeng Ma , Jianghui Du , Haobing Yan , Chaobin Shi
Molybdenum disulfide (MoS2) is considered a favorable absorbent for removing heavy metals. However, due to its various morphologies, MoS2 exhibits significant differences in its performance for removing mercury from flue gas. In the present study, the flower-like, spherical MoS2 and W-MoS2 were prepared by regulating the interlayer spacing and doping tungsten (W) in MoS2 for removing gaseous mercury (Hg0). The results show that the number of active sulfur sites (S2- and S22-) was critical to the adsorption performance of MoS2 for Hg0. The flower-like MoS2 demonstrated optimum properties below 125°C which attributed to the presence of dominated S2- sites, while spherical MoS2 and W-MoS2 showed a wider application temperature range (up to 175°C) during Hg0 removal which attributed to the unsaturated sulfur S22- and active oxygen. In terms of the mechanism, Hg0 is directly inserted into the Mo-S bond of MoS2 to form a transition state [Hg·Mo]-S, and then the original Mo-S is interrupted to form a new β-Hg-S bond, or combine with surface oxidation to form HgO. The oxygen in the flue gas can supplement the surface active oxygen on the MoS2, which enables the circulation of Mo5+. Hg0 also reacted with S22- to form α-HgS.
{"title":"Controlling morphology and doping tungsten to regulate sulfur species on molybdenum disulfide for removing Hg0 from flue gas","authors":"Yongpeng Ma , Jianghui Du , Haobing Yan , Chaobin Shi","doi":"10.1080/17415993.2025.2453751","DOIUrl":"10.1080/17415993.2025.2453751","url":null,"abstract":"<div><div>Molybdenum disulfide (MoS<sub>2</sub>) is considered a favorable absorbent for removing heavy metals. However, due to its various morphologies, MoS<sub>2</sub> exhibits significant differences in its performance for removing mercury from flue gas. In the present study, the flower-like, spherical MoS<sub>2</sub> and W-MoS<sub>2</sub> were prepared by regulating the interlayer spacing and doping tungsten (W) in MoS<sub>2</sub> for removing gaseous mercury (Hg<sup>0</sup>). The results show that the number of active sulfur sites (S<sup>2-</sup> and S<sub>2</sub><sup>2-</sup>) was critical to the adsorption performance of MoS<sub>2</sub> for Hg<sup>0</sup>. The flower-like MoS<sub>2</sub> demonstrated optimum properties below 125°C which attributed to the presence of dominated S<sup>2-</sup> sites, while spherical MoS<sub>2</sub> and W-MoS<sub>2</sub> showed a wider application temperature range (up to 175°C) during Hg<sup>0</sup> removal which attributed to the unsaturated sulfur S<sub>2</sub><sup>2-</sup> and active oxygen. In terms of the mechanism, Hg<sup>0</sup> is directly inserted into the Mo-S bond of MoS<sub>2</sub> to form a transition state [Hg·Mo]-S, and then the original Mo-S is interrupted to form a new β-Hg-S bond, or combine with surface oxidation to form HgO. The oxygen in the flue gas can supplement the surface active oxygen on the MoS<sub>2</sub>, which enables the circulation of Mo<sup>5+</sup>. Hg<sup>0</sup> also reacted with S<sub>2</sub><sup>2-</sup> to form α-HgS.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 3","pages":"Pages 435-454"},"PeriodicalIF":2.1,"publicationDate":"2025-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144105787","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-04DOI: 10.1080/17415993.2025.2473737
Nasser Zarinderakht , Mohammad Abbasi , Najmeh Nowrouzi
A new efficient, one-pot method to get thiobenzamide compounds from benzyl halides, amines, and Na2S2O3 is reported. A benzylic halide is treated with Na2S2O3 in DMSO until the halide is completely consumed. Next, the reaction is continued by adding a primary or secondary amine to the reaction mixture to synthesize thiobenzamides simply. This procedure does not require a special catalyst or any additive to afford thiobenzamides in good to excellent yields.
{"title":"Self-catalyzed, reaction of benzyl halides, Na2S2O3, and amines: a one-pot, simple, and efficient route to thiobenzamides","authors":"Nasser Zarinderakht , Mohammad Abbasi , Najmeh Nowrouzi","doi":"10.1080/17415993.2025.2473737","DOIUrl":"10.1080/17415993.2025.2473737","url":null,"abstract":"<div><div>A new efficient, one-pot method to get thiobenzamide compounds from benzyl halides, amines, and Na<sub>2</sub>S<sub>2</sub>O<sub>3</sub> is reported. A benzylic halide is treated with Na<sub>2</sub>S<sub>2</sub>O<sub>3</sub> in DMSO until the halide is completely consumed. Next, the reaction is continued by adding a primary or secondary amine to the reaction mixture to synthesize thiobenzamides simply. This procedure does not require a special catalyst or any additive to afford thiobenzamides in good to excellent yields.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 3","pages":"Pages 393-400"},"PeriodicalIF":2.1,"publicationDate":"2025-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144105786","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-05-04DOI: 10.1080/17415993.2025.2459181
G.S.M. Sundaram , Vijay Sharma
Diagnostic agents capable of imaging β-amyloid (Aβ) plaques at prodromal stages could provide noninvasive tools to assess plaque burden and assist in determining efficacy of disease-modifying therapeutic interventions in vivo. To accomplish this goal, FDA approved 18F-incorporated tracers, such as Florbetapir, Flutemetamol, and Florbetaben may allow quantitative analysis of therapeutic efficacy of disease-modifying treatments that attenuate Aβ pathophysiology in vivo. Although promising, these tracers show high off-target binding. Importantly, current anti-amyloid therapy also targets diffuse amyloid plaques (included in revised NIAAA criteria for detecting AD) and other forms of amyloid plaques. Therefore, molecules capable of detecting both diffuse and fibrillar plaque pathology can potentially offer better quantitative tools for interrogating efficacy of anti-amyloid therapy. To achieve this goal, herein, we report synthesis and characterization of new small organic molecules: ((Z,E)-4-(2-(6-(2-Fluoroethoxy)benzo[d]thiazol-2-yl)vinyl)-N,N-dimethylaniline) 4, ((Z)-4-(2-(6-(2-(2-(3-Fluoropropoxy)ethoxy)ethoxy)benzo[d]thiazol-2-yl)vinyl)-N,N-dimethylaniline) 5a and ((E)-4-(2-(6-(2-(2-(3-Fluoropropoxy)ethoxy)ethoxy)benzo[d]thiazol-2-yl)vinyl)-N,N-dimethylaniline) 5b. We also report preliminary investigations on binding affinity in vitro. While 4 demonstrated a relatively higher affinity, both 5a and 5b showed moderate affinity for Aβ1-42 aggregates in vitro. Furthermore, all 3 agents showed ability to detect Aβ fibrillar and diffuse plaque pathology in brain sections of APP/PS1 transgenic mice and post-mortem confirmed AD human brain tissue sections.
能够在前驱阶段成像β-淀粉样蛋白（Aβ）斑块的诊断试剂可以提供无创工具来评估斑块负担，并协助确定体内疾病改善治疗干预措施的疗效。为了实现这一目标，FDA批准了含18f的示踪剂，如Florbetapir、Flutemetamol和Florbetaben，可以定量分析减轻体内Aβ病理生理的疾病修饰治疗的治疗效果。尽管这些示踪剂很有前景，但它们表现出高度的脱靶结合。重要的是，目前的抗淀粉样蛋白治疗也针对弥漫性淀粉样蛋白斑块（包括在NIAAA检测AD的修订标准中）和其他形式的淀粉样蛋白斑块。因此，能够检测弥漫性和纤维斑块病理的分子可能为询问抗淀粉样蛋白治疗的疗效提供更好的定量工具。为了实现这一目标，本文报道了新的有机小分子的合成和表征：((Z，E)-4-（2-（6-（2-（3-氟丙氧基）苯并[d]噻唑-2-基）乙烯基）- n， n -二甲基苯胺）4,（（Z)-4-（2-（2-（2-（3-氟丙氧基）乙氧基）苯并[d]噻唑-2-基）乙烯基）- n， n -二甲基苯胺）5a和（E)-4-（2-（2-（3-氟丙氧基）乙氧基）苯并[d]噻唑-2-基）乙烯基）- n， n -二甲基苯胺）5b。我们还报道了体外结合亲和力的初步研究。4具有较高的亲和力，而5a和5b在体外均对a β1-42聚集体具有中等的亲和力。此外，这3种药物均能检测APP/PS1转基因小鼠脑切片和死后证实的AD人脑组织切片中的β纤维和弥漫性斑块病理。
{"title":"Small molecule heterocycles: design and synthesis of novel fluorescent Benzothiazoles for early detection of Alzheimer’s disease","authors":"G.S.M. Sundaram , Vijay Sharma","doi":"10.1080/17415993.2025.2459181","DOIUrl":"10.1080/17415993.2025.2459181","url":null,"abstract":"<div><div>Diagnostic agents capable of imaging β-amyloid (Aβ) plaques at prodromal stages could provide noninvasive tools to assess plaque burden and assist in determining efficacy of disease-modifying therapeutic interventions in vivo. To accomplish this goal, FDA approved <sup>18</sup>F-incorporated tracers, such as Florbetapir, Flutemetamol, and Florbetaben may allow quantitative analysis of therapeutic efficacy of disease-modifying treatments that attenuate Aβ pathophysiology <em>in vivo</em>. Although promising, these tracers show high off-target binding. Importantly, current anti-amyloid therapy also targets diffuse amyloid plaques (included in revised NIAAA criteria for detecting AD) and other forms of amyloid plaques. Therefore, molecules capable of detecting both diffuse and fibrillar plaque pathology can potentially offer better quantitative tools for interrogating efficacy of anti-amyloid therapy. To achieve this goal, herein, we report synthesis and characterization of new small organic molecules: ((<em>Z,E</em>)-4-(2-(6-(2-Fluoroethoxy)benzo[d]thiazol-2-yl)vinyl)-<em>N,N</em>-dimethylaniline) <strong>4</strong>, ((<em>Z</em>)-4-(2-(6-(2-(2-(3-Fluoropropoxy)ethoxy)ethoxy)benzo[d]thiazol-2-yl)vinyl)-<em>N,N</em>-dimethylaniline) <strong>5a</strong> and ((<em>E</em>)-4-(2-(6-(2-(2-(3-Fluoropropoxy)ethoxy)ethoxy)benzo[d]thiazol-2-yl)vinyl)-<em>N,N</em>-dimethylaniline) <strong>5b.</strong> We also report preliminary investigations on binding affinity in vitro. While <strong>4</strong> demonstrated a relatively higher affinity, both <strong>5a</strong> and <strong>5b</strong> showed moderate affinity for Aβ<sub>1-42</sub> aggregates <em>in vitro</em>. Furthermore, all 3 agents showed ability to detect Aβ fibrillar and diffuse plaque pathology in brain sections of APP/PS1 transgenic mice and post-mortem confirmed AD human brain tissue sections.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 3","pages":"Pages 505-512"},"PeriodicalIF":2.1,"publicationDate":"2025-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144105793","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-04DOI: 10.1080/17415993.2024.2440046
Maheen Riaz , Muhammad Taha Qureshi , Firdous Imran Ali , Shoaib Muhammad , Ahmed Bari , William Henderson , Imran Ali Hashmi
A new hydrophobic ionic liquid 1,3-dihexylimidazolium-5-sulfosalicylate [DHIm] + [5-SSA]− was synthesized and characterized. The sulfonic-functionalized IL was effectively employed in the Biginelli reaction under ultrasound irradiation. The [DHIm] + [5-SSA]− demonstrated efficient catalytic performance yielding up to 83% product. Additionally, the application of [DHIm] + [5-SSA]− in selective extraction of Co2+ and Ni2+ from their aqueous mixture has been successfully carried out. High extraction efficiency was observed for Co2+.
{"title":"Sulfonic group functionalized task specific ionic liquid as catalyst for Biginelli reaction in water and Co2+/Ni2+ separation from their aqueous mixture","authors":"Maheen Riaz , Muhammad Taha Qureshi , Firdous Imran Ali , Shoaib Muhammad , Ahmed Bari , William Henderson , Imran Ali Hashmi","doi":"10.1080/17415993.2024.2440046","DOIUrl":"10.1080/17415993.2024.2440046","url":null,"abstract":"<div><div>A new hydrophobic ionic liquid 1,3-dihexylimidazolium-5-sulfosalicylate [DHIm] <sup>+ </sup>[5-SSA]<sup>−</sup> was synthesized and characterized. The sulfonic-functionalized IL was effectively employed in the Biginelli reaction under ultrasound irradiation. The [DHIm] <sup>+ </sup>[5-SSA]<sup>−</sup> demonstrated efficient catalytic performance yielding up to 83% product. Additionally, the application of [DHIm] <sup>+ </sup>[5-SSA]<sup>−</sup> in selective extraction of Co<sup>2+</sup> and Ni<sup>2+</sup> from their aqueous mixture has been successfully carried out. High extraction efficiency was observed for Co<sup>2+</sup>.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 2","pages":"Pages 272-290"},"PeriodicalIF":2.1,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143577456","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-04DOI: 10.1080/17415993.2025.2457347
Esmail Vessally , Bayan Azizi , Qusay Husam Aziz , Karrar R. Al-Shami , Hayder Tariq , Farnaz Behmagham , Azadeh Khanmohammadi
In this study, the adsorption behavior of sulfur mustard on metal porphyrins replaced in carbon nanocone (M-PCNC, M = Fe2+ and Mg2+) is explored using density functional theory (DFT) calculations. Energetics, physical parameters, and electronic properties are determined utilizing the M06-2X approach and the 6-31G(d) basis set. Based on the obtained results, the sulfur mustard exhibits strong adsorption onto the M-PCNCs, which denotes a chemisorption process between species. Furthermore, the findings suggest that the M-PCNCs are effective adsorbents in eliminating undesired sulfur mustard molecules from the surroundings. The data also show that the energy gap (or work function) of the M-PCNC structures is not affected by the adsorption of sulfur mustard, suggesting that they are unsuitable for use as sensors for the sulfur mustard in terms of electronic conductivity or work function. The UV-visible spectra of bare Fe-PCNC are also compared to its corresponding complexes, which reveals the adsorption of sulfur mustard does not alter the spectra of the Fe-PCNC and cannot act as a UV-based sensitive material for detecting sulfur mustard.
本文利用密度泛函理论（DFT）研究了硫芥在碳纳米锥（M- pcnc, M = Fe2+和Mg2+）金属卟啉上的吸附行为。利用M06-2X方法和6-31G(d)基准集确定能量学、物理参数和电子特性。结果表明，芥菜在M-PCNCs上表现出较强的吸附作用，表明存在种间的化学吸附过程。此外，研究结果表明，M-PCNCs是一种有效的吸附剂，可以从周围环境中去除不需要的芥子气分子。数据还表明，M-PCNC结构的能隙（或功函数）不受芥菜吸附的影响，这表明它们在电子电导率或功函数方面不适合用作芥菜传感器。对裸态Fe-PCNC的紫外可见光谱与相应配合物的紫外可见光谱进行了比较，结果表明，对芥菜的吸附不会改变Fe-PCNC的光谱，不能作为检测芥菜的紫外敏感材料。
{"title":"DFT, TD-DFT, QTAIM and NBO investigations of the interaction between sulfur mustard and metal porphyrins induced in carbon nanocone (M-PCNC, M = Fe2+ and Mg2+)","authors":"Esmail Vessally , Bayan Azizi , Qusay Husam Aziz , Karrar R. Al-Shami , Hayder Tariq , Farnaz Behmagham , Azadeh Khanmohammadi","doi":"10.1080/17415993.2025.2457347","DOIUrl":"10.1080/17415993.2025.2457347","url":null,"abstract":"<div><div>In this study, the adsorption behavior of sulfur mustard on metal porphyrins replaced in carbon nanocone (M-PCNC, M = Fe<sup>2+</sup> and Mg<sup>2+</sup>) is explored using density functional theory (DFT) calculations. Energetics, physical parameters, and electronic properties are determined utilizing the M06-2X approach and the 6-31G(d) basis set. Based on the obtained results, the sulfur mustard exhibits strong adsorption onto the M-PCNCs, which denotes a chemisorption process between species. Furthermore, the findings suggest that the M-PCNCs are effective adsorbents in eliminating undesired sulfur mustard molecules from the surroundings. The data also show that the energy gap (or work function) of the M-PCNC structures is not affected by the adsorption of sulfur mustard, suggesting that they are unsuitable for use as sensors for the sulfur mustard in terms of electronic conductivity or work function. The UV-visible spectra of bare Fe-PCNC are also compared to its corresponding complexes, which reveals the adsorption of sulfur mustard does not alter the spectra of the Fe-PCNC and cannot act as a UV-based sensitive material for detecting sulfur mustard.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 2","pages":"Pages 291-311"},"PeriodicalIF":2.1,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143576752","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-04DOI: 10.1080/17415993.2024.2420090
Nurul Fatimah Abdul Basir , Mahta Ghafarikhaligh , Mohd Rafie Johan , Nader Ghaffari Khaligh
Regarding the importance of 1,3,4-thiadiazoles due to versatile biological activity and for investigation of the symmetry impact on thermal behavior and antibacterial activity of 2,5-bisalkylsulfenyl[1,3,4]thiadiazole, two new derivatives viz. 2-cyclohexylsulfenyl-5-cyclopentylsulfenyl[1,3,4]thiadiazole and 2-cyclohexylsulfenyl-5-dodecylsulfenyl[1,3,4]thiadiazole, were synthesized through the nucleophilic substitution reaction appropriate alkyl halide with 5-cyclohexyl-3H-[1,3,4]thiadiazole-2-thione in ethanol under reflux conditions. The chemical structure of the products was elucidated by the physical and spectroscopic techniques. After tedious work, the suitable snow-like crystals of 2-cyclohexylsulfenyl-5-dodecylsulfenyl[1,3,4]thiadiazole for single-crystal X-ray diffraction analysis could be isolated from a mixed solvent, namely ethanol and water in volume ratio of 9:1. Then, the influence of symmetry and cyclic or non-cyclic aliphatic substituents on the important structure parameters of the 2,5-bisalkylsulfenyl[1,3,4]thiadiazole derivatives were negligible, however, those structure characteristics were different for 5–cyclohexylsulfenyl–3H–[1,3,4]thiadiazole–2–thione, due to its thione structure. TGA/DTA study demonstrated the effect of the symmetry and van der Waals interaction on thermal stability, and the robust influence of the pseudo hydrogen bonding NH with C = S on the melting and crystallization phase transitions was revealed by DSC analysis. The pharmacokinetics, drug-likeness, medicinal chemistry friendliness, and toxicology of three derivatives of bis-alkylsulfenyl[1,3,4]thiadiazole were evaluated by two prediction tools of SwissADME and T.E.S.T tools predicted good pharmacokinetics, drug-likeness, and anti-toxicant properties in developmental toxicity for the bis-alkylsulfenyl[1,3,4]thiadiazoles and 5–cyclohexylsulfenyl–3H–[1,3,4]thiadiazole–2–thione. Finally, the in vitro antibacterial activity of two new 2-cyclohexylsulfenyl-5-cyclopentylsulfenyl[1,3,4]thiadiazole and 2-cyclohexylsulfenyl-5-dodecylsulfenyl[1,3,4]thiadiazole against S. aureus and E. coli, confirmed them as promising anti-bacterial agent. All obtained results proved that the physicochemical, thermal, pharmacokinetic, and biological properties of 2,5-bisalkylsulfenyl[1,3,4]thiadiazoles can be tuned by selecting appropriate substituents.
{"title":"Synthesis and characterization of two asymmetrical 2-cyclohexylsulfenyl-5-alkylsulfenyl[1,3,4]thiadiazoles and study the impact of substituents on the structural features, thermal behavior, and anti-bacterial activity","authors":"Nurul Fatimah Abdul Basir , Mahta Ghafarikhaligh , Mohd Rafie Johan , Nader Ghaffari Khaligh","doi":"10.1080/17415993.2024.2420090","DOIUrl":"10.1080/17415993.2024.2420090","url":null,"abstract":"<div><div>Regarding the importance of 1,3,4-thiadiazoles due to versatile biological activity and for investigation of the symmetry impact on thermal behavior and antibacterial activity of 2,5-bisalkylsulfenyl[1,3,4]thiadiazole, two new derivatives viz. 2-cyclohexylsulfenyl-5-cyclopentylsulfenyl[1,3,4]thiadiazole and 2-cyclohexylsulfenyl-5-dodecylsulfenyl[1,3,4]thiadiazole, were synthesized through the nucleophilic substitution reaction appropriate alkyl halide with 5-cyclohexyl-3<em>H</em>-[1,3,4]thiadiazole-2-thione in ethanol under reflux conditions. The chemical structure of the products was elucidated by the physical and spectroscopic techniques. After tedious work, the suitable snow-like crystals of 2-cyclohexylsulfenyl-5-dodecylsulfenyl[1,3,4]thiadiazole for single-crystal X-ray diffraction analysis could be isolated from a mixed solvent, namely ethanol and water in volume ratio of 9:1. Then, the influence of symmetry and cyclic or non-cyclic aliphatic substituents on the important structure parameters of the 2,5-bisalkylsulfenyl[1,3,4]thiadiazole derivatives were negligible, however, those structure characteristics were different for 5–cyclohexylsulfenyl–3<em>H</em>–[1,3,4]thiadiazole–2–thione, due to its thione structure. TGA/DTA study demonstrated the effect of the symmetry and van der Waals interaction on thermal stability, and the robust influence of the pseudo hydrogen bonding NH with C = S on the melting and crystallization phase transitions was revealed by DSC analysis. The pharmacokinetics, drug-likeness, medicinal chemistry friendliness, and toxicology of three derivatives of bis-alkylsulfenyl[1,3,4]thiadiazole were evaluated by two prediction tools of SwissADME and T.E.S.T tools predicted good pharmacokinetics, drug-likeness, and anti-toxicant properties in developmental toxicity for the bis-alkylsulfenyl[1,3,4]thiadiazoles and 5–cyclohexylsulfenyl–3<em>H</em>–[1,3,4]thiadiazole–2–thione. Finally, the <em>in vitro</em> antibacterial activity of two new 2-cyclohexylsulfenyl-5-cyclopentylsulfenyl[1,3,4]thiadiazole and 2-cyclohexylsulfenyl-5-dodecylsulfenyl[1,3,4]thiadiazole against <em>S. aureus</em> and <em>E. coli</em>, confirmed them as promising anti-bacterial agent. All obtained results proved that the physicochemical, thermal, pharmacokinetic, and biological properties of 2,5-bisalkylsulfenyl[1,3,4]thiadiazoles can be tuned by selecting appropriate substituents.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 2","pages":"Pages 191-211"},"PeriodicalIF":2.1,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143577460","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-04DOI: 10.1080/17415993.2024.2449383
Francinara Alves , Rafael Oliveira , Helivaldo Souza , Priscila Lima , Fellipe Farias , Bruna Marzari , Helena Coelho , José Luis , Petrônio Athayde-Filho , Gabriela Fiss
Motivated to expand the investigation of the antimicrobial profile of 2-selenocetanilides and ebselen analogue, four compounds were prepared using a cleaner method in water as a solvent. Thus, 2-selenoacetanilides were obtained by the alkylation reaction of 2-chloroacetanilides with benzoyl (or phthalylglycyl) selenoate generated in situ under mild conditions. New compound 3a was submitted to single crystal X-ray diffraction, where only the Z-conformer was observed. In silico ADMET test was required to predicate the drug-like character of 2-selenoacetanilides, where, with exception of substituted 2-selenocetanilides that are probably mutagenic, all compounds predicted positive characteristics of lipophilicity, absorption, solubility and toxicity. Antimicrobial search for 2-selenoacetanilides was expanded, showing activity against 10 of 15 microorganisms tested, with MICs ≤ 80 µg.mL−1, including a medium pathogen (Cryptococcus gattii), high pathogens (Candida glabrata and C. tropicalis), a critical pathogen (Aspergillus fumigatus), in addition to Klebsiella pneumoniae, known as a superbug. The results indicate the emergence of compound 3a as a potential fungicidal against C. gattii, with MIC/MFC of 2.5 µg.mL−1, in comparison to the standard drug fluconazole, as well as compound 4c as a potential antimicrobial against K. pneumoniae and C. gattii, with MIC/MBC/MFC of 10 µg.mL−1, i.e. a new candidate to combat co-infection.
{"title":"Cleaner approach and antimicrobial screening of 2-selenoacetanilides: emergence of potential agents against co-infection","authors":"Francinara Alves , Rafael Oliveira , Helivaldo Souza , Priscila Lima , Fellipe Farias , Bruna Marzari , Helena Coelho , José Luis , Petrônio Athayde-Filho , Gabriela Fiss","doi":"10.1080/17415993.2024.2449383","DOIUrl":"10.1080/17415993.2024.2449383","url":null,"abstract":"<div><div>Motivated to expand the investigation of the antimicrobial profile of 2-selenocetanilides and ebselen analogue, four compounds were prepared using a cleaner method in water as a solvent. Thus, 2-selenoacetanilides were obtained by the alkylation reaction of 2-chloroacetanilides with benzoyl (or phthalylglycyl) selenoate generated <em>in situ</em> under mild conditions. New compound <strong>3a</strong> was submitted to single crystal X-ray diffraction, where only the <em>Z</em>-conformer was observed. <em>In silico</em> ADMET test was required to predicate the drug-like character of 2-selenoacetanilides, where, with exception of substituted 2-selenocetanilides that are probably mutagenic, all compounds predicted positive characteristics of lipophilicity, absorption, solubility and toxicity. Antimicrobial search for 2-selenoacetanilides was expanded, showing activity against 10 of 15 microorganisms tested, with MICs ≤ 80 µg.mL<sup>−1</sup>, including a medium pathogen (<em>Cryptococcus gattii</em>), high pathogens (<em>Candida glabrata</em> and <em>C. tropicalis</em>), a critical pathogen (<em>Aspergillus fumigatus</em>), in addition to <em>Klebsiella pneumoniae</em>, known as a superbug. The results indicate the emergence of compound <strong>3a</strong> as a potential fungicidal against <em>C. gattii</em>, with MIC/MFC of 2.5 µg.mL<sup>−1</sup>, in comparison to the standard drug fluconazole, as well as compound <strong>4c</strong> as a potential antimicrobial against <em>K. pneumoniae</em> and <em>C. gattii</em>, with MIC/MBC/MFC of 10 µg.mL<sup>−1</sup>, <em>i.e.</em> a new candidate to combat co-infection.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 2","pages":"Pages 212-225"},"PeriodicalIF":2.1,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143577458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-04DOI: 10.1080/17415993.2024.2416237
Alaa A. Al-Yaseen , Mouayed A. Hussein
A novel copper complex of [CuII (μ2–S)(terminal-S)(2-acetylpyrdine oxime)2 (1) is synthesized and characterized by X-ray single-crystal diffraction. The free ligand of 2-acetylpyrdine oxime is an unexpected product obtained from a condensation reaction of p-aminobenzene sulfonamide and 2-acetylpyridine and is characterized by IR, 1HNMR, and 13CNMR spectroscopic methods. X-ray crystallography showed strictly planar bridged μ2- Cu2(S)2 core, and each copper(II) center exhibits distorted square pyramidal coordination geometry. The cytotoxicity of the complex was tested in vitro against esophageal cancer (SKGT-4) cell lines by metabolic tests, using 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide as a reagent. Complex 1 showed a remarkable inhibition response in SKGT-4 cell lines.
{"title":"The first type of binuclear copper complex with terminal sulfide: synthesis, structural characterization, and cytotoxicity evaluation","authors":"Alaa A. Al-Yaseen , Mouayed A. Hussein","doi":"10.1080/17415993.2024.2416237","DOIUrl":"10.1080/17415993.2024.2416237","url":null,"abstract":"<div><div>A novel copper complex of [Cu<sup>II</sup> (μ<sub>2</sub>–S)(terminal-S)(2-acetylpyrdine oxime)<sub>2</sub> (<strong>1</strong>) is synthesized and characterized by X-ray single-crystal diffraction. The free ligand of 2-acetylpyrdine oxime is an unexpected product obtained from a condensation reaction of p-aminobenzene sulfonamide and 2-acetylpyridine and is characterized by IR, <sup>1</sup>HNMR, and <sup>13</sup>CNMR spectroscopic methods. X-ray crystallography showed strictly planar bridged μ<sub>2</sub>- Cu<sub>2</sub>(S)<sub>2</sub> core, and each copper(II) center exhibits distorted square pyramidal coordination geometry. The cytotoxicity of the complex was tested in vitro against esophageal cancer (SKGT-4) cell lines by metabolic tests, using 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide as a reagent. Complex <strong>1</strong> showed a remarkable inhibition response in SKGT-4 cell lines.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 2","pages":"Pages 345-357"},"PeriodicalIF":2.1,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143576753","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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