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Computational investigation of the isomers formed from the reaction S2 + O2 S2 + O2反应生成异构体的计算研究
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-05-04 Epub Date: 2025-03-06 DOI: 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.
二硫(3S2)与氧3S2 + 3O2的反应是硫燃烧过程中产生不同的1S2O2异构体和随后的分子内异构化反应的重要反应。本文用四种不同的量子化学方法对3S2 + 3O2的反应路径和产物进行了计算研究。详细评价了该体系中物质的异构化和离解反应的热化学性质,并报道了反应路径和能垒。焓在CBS-QB3, G3B3, G4能级上计算,如果可能的话,在W1U能级上计算。熵和热容对温度的贡献由分子结构、转动惯量和振动频率决定。根据计算的热化学数据,估计了双分子化学活化分析中反应路径和动力学参数作为温度函数的重要性。高压极限动力学参数由典型过渡态理论(TST)计算得到。结果表明:1SS(=O)=O、3SO、1SO2和3S为低能产物。
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引用次数: 0
Self-catalyzed, reaction of benzyl halides, Na2S2O3, and amines: a one-pot, simple, and efficient route to thiobenzamides 苯基卤化物、Na2S2O3和胺的自催化反应:一锅制硫苯酰胺的简单有效途径
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-05-04 Epub Date: 2025-03-07 DOI: 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.
报道了一种从卤苄、胺和Na2S2O3中提取硫代苯甲酰胺化合物的高效一锅法。苯基卤化物在DMSO中用Na2S2O3处理,直到卤化物完全消耗。接下来,通过在反应混合物中加入伯胺或仲胺来继续反应,以简单地合成硫苯酰胺。这个过程不需要特殊的催化剂或任何添加剂,以提供良好的到优异的产量的硫苯酰胺。
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引用次数: 0
Small molecule heterocycles: design and synthesis of novel fluorescent Benzothiazoles for early detection of Alzheimer’s disease 小分子杂环:用于阿尔茨海默病早期检测的新型荧光苯并噻唑的设计和合成
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-05-04 Epub Date: 2025-02-25 DOI: 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。
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引用次数: 0
Sulfonic group functionalized task specific ionic liquid as catalyst for Biginelli reaction in water and Co2+/Ni2+ separation from their aqueous mixture 磺酸基功能化任务特异性离子液体作为催化剂,用于水中Biginelli反应和Co2+/Ni2+水溶液的分离
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2024-12-12 DOI: 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+.
合成了一种新型疏水离子液体1,3-二己基咪唑-5-磺基水杨酸[DHIm] + [5-SSA]−,并对其进行了表征。在超声照射下,磺化IL有效地用于Biginelli反应。[DHIm] + [5-SSA]−表现出高效的催化性能,产率高达83%。此外,还成功地将[DHIm] + [5-SSA]−应用于Co2+和Ni2+的选择性萃取。对Co2+有较高的萃取效率。
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引用次数: 0
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+) 碳纳米锥(M- pcnc, M = Fe2+和Mg2+)中硫芥与金属卟啉相互作用的DFT、TD-DFT、QTAIM和NBO研究
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2025-02-04 DOI: 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。
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引用次数: 0
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 两个不对称2-环己基亚砜基-5-烷基亚砜基[1,3,4]噻二唑的合成与表征,并研究取代基对其结构特征、热行为和抗菌活性的影响
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2024-10-24 DOI: 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.
鉴于1,3,4-噻二唑具有广泛的生物活性,并对2,5-双烷基磺酰基[1,3,4]噻二唑的热行为和抗菌活性的对称性影响进行了研究,提出了两个新的衍生物,即2-环己基磺酰基-5-环戊基磺酰基[1,3,4]噻二唑和2-环己基磺酰基-5-十二烷基磺酰基[1,3,4]噻二唑,与5-环己基- 3h -[1,3,4]噻二唑-2-硫酮在乙醇回流条件下通过亲核取代反应合成合适的卤代烷基。通过物理和光谱技术对产物的化学结构进行了分析。经过繁琐的工作,从体积比为9:1的混合溶剂即乙醇和水中分离出适合用于x射线单晶衍射分析的2-环己基磺酰基-5-十二烷基磺酰基[1,3,4]噻二唑的雪状晶体。然后,对称和环状或非环状脂肪取代基对2,5-双烷基磺酰基[1,3,4]噻二唑衍生物的重要结构参数的影响可以忽略不计,而5-环己基磺酰基- 3h -[1,3,4]噻二唑- 2 -硫酮由于其硫酮结构而具有不同的结构特征。热重分析(TGA/DTA)证明了对称和范德华相互作用对热稳定性的影响,DSC分析揭示了C = S的伪氢键NH对熔融和结晶相变的强大影响。采用SwissADME和T.E.S.T两种预测工具对三种双烷基磺酰基[1,3,4]噻二唑衍生物的药代动力学、药物相似性、药物化学友好性和毒理学进行了评价。两种预测工具预测了双烷基磺酰基[1,3,4]噻二唑和5 -环己基磺酰基- 3h -[1,3,4]噻二唑- 2 -硫酮具有良好的药代动力学、药物相似性和抗发育毒性。最后,对两种新型2-环己基磺酰基-5-环戊基磺酰基[1,3,4]噻二唑和2-环己基磺酰基-5-十二烷基磺酰基[1,3,4]噻二唑对金黄色葡萄球菌和大肠杆菌的体外抑菌活性进行了研究,证实了它们是很有前景的抗菌药物。结果表明,2,5-双烷基亚砜基[1,3,4]噻二唑的理化、热、药代动力学和生物学性质可以通过选择合适的取代基来调节。
{"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 ,&nbsp;Mahta Ghafarikhaligh ,&nbsp;Mohd Rafie Johan ,&nbsp;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}
引用次数: 0
Cleaner approach and antimicrobial screening of 2-selenoacetanilides: emergence of potential agents against co-infection 2-硒代乙酰苯胺的清洁方法和抗菌筛选:抗合并感染的潜在药物的出现
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2025-01-08 DOI: 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.
为了扩大对2-硒辛烷酰类化合物和依布硒类似物抗菌特性的研究,以水为溶剂,采用清洁法制备了4种化合物。因此,在温和条件下,2-氯乙酰苯胺与苯甲酰(或邻苯二甲酸乙酯)硒酸盐原位烷基化反应得到2-硒代乙酰苯胺。对新化合物3a进行单晶x射线衍射,只观察到z形构象。在硅中需要ADMET测试来预测2-硒代乙酰苯胺的药物样特性,其中,除了取代的2-硒代乙酰苯胺可能具有诱变性外,所有化合物都预测了亲脂性、吸收性、溶解度和毒性的阳性特性。扩大了2-硒乙酰苯胺的抗菌搜索,显示对15种微生物中的10种有活性,mic≤80µg。mL−1,包括中等病原体(加蒂隐球菌)、高致病菌(光念珠菌和热带假丝酵母)、临界病原体(烟曲霉),此外还有肺炎克雷伯菌,称为超级细菌。结果表明,化合物3a具有潜在的杀真菌活性,其MIC/MFC为2.5µg。mL−1,与标准药物氟康唑相比,以及化合物4c作为潜在的抗肺炎克雷伯菌和C.加蒂菌,MIC/MBC/MFC为10µg。mL−1,即抗共感染的新候选物。
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引用次数: 0
The first type of binuclear copper complex with terminal sulfide: synthesis, structural characterization, and cytotoxicity evaluation 第一类末端硫化物双核铜配合物:合成、结构表征及细胞毒性评价
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2024-10-30 DOI: 10.1080/17415993.2024.2416237
Alaa A. Al-Yaseen , Mouayed A. Hussein
A novel copper complex of [CuII2–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.
合成了一种新型铜配合物[CuII (μ2-S)(末端- s)(2-乙酰吡啶肟)2(1)],并用x射线单晶衍射对其进行了表征。2-乙酰吡啶肟的游离配体是对氨基苯磺酰胺与2-乙酰吡啶缩合反应的意外产物,并通过IR、1HNMR和13CNMR光谱方法进行了表征。x射线晶体学显示μ2- Cu2(S)2核心呈严格的平面桥接,各铜(II)中心呈畸变的方锥体配位几何。以3-(4,5 -二甲基噻唑-2-基)-2,5-二苯基溴化四氮唑为试剂,通过代谢试验检测了该复合物对食管癌(SKGT-4)细胞株的体外细胞毒性。复合物1在SKGT-4细胞系中表现出显著的抑制作用。
{"title":"The first type of binuclear copper complex with terminal sulfide: synthesis, structural characterization, and cytotoxicity evaluation","authors":"Alaa A. Al-Yaseen ,&nbsp;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}
引用次数: 0
Thiolaryl substituted β-lactams as important capping agents for hafnia nanoparticles 硫代芳基取代β-内酰胺作为半氟纳米粒子的重要封盖剂
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2024-12-06 DOI: 10.1080/17415993.2024.2437392
Aarti Thakur , Mehar Singh , Preeti Garg , Renu Thapar
A new study on the synthesis of β-lactams functionalized hafnia nanoparticles is done. The reported work describes the utility of hydrothermal method to prepare hafnia nanoparticles coated with β-lactams. The method provides spherical NPs with dimensions of 30–50 nm and are slightly anionic. The conjugate has been found to be biologically active and well characterized by techniques like FTIR, XRD, FESEM, TEM, and EDX methods. The methodology gives a conjugate whose synthesis has not been attempted so far in the literature.
本研究对β-内酰胺功能化霞糠纳米粒子的合成进行了一项新的研究。报告介绍了水热法制备涂覆有β-内酰胺的霞糠纳米粒子的实用性。该方法制备的球形 NPs 尺寸为 30-50 nm,略带阴离子。通过傅立叶变换红外光谱(FTIR)、XRD、FESEM、TEM 和 EDX 方法等技术,发现该共轭物具有良好的生物活性和特性。该方法提供了一种迄今为止文献中尚未尝试过合成的共轭物。
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引用次数: 0
Design, synthesis, characterization, antimicrobial evaluations and molecular docking studies of 5-(phenylcarbamoyl)pentylselenyl tethered ester, acid and trans-β-lactams 5-(苯基氨基甲酰)戊硒基系链酯、酸和反式β-内酰胺的设计、合成、表征、抗菌评价和分子对接研究
IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-03-04 Epub Date: 2024-12-11 DOI: 10.1080/17415993.2024.2438869
Dipika Narula , Shamsher S. Bari , Love Singla , Aman Bhalla
Herein, we unveil the utility of bis(5-phenylcarbamoylpentyl)diselenide 2 for obtaining unique seleno-ester viz ethyl 2-(5-(phenylcarbamoyl)pentylselenyl)ethanoate 3 and further transformation of 3 to 2-(5-(phenylcarbamoyl)pentylselenyl)ethanoic acid 4. Next, time-efficient (complete in 15 min.) and stereoselective synthesis of trans-3-((5-phenylcarbamoyl)pentylselenyl)-β-lactams 6a-d (52-78% yields) starting from seleno-acid 4 and substituted imines 5a-d has been reported with relevant characterization data (FT-IR, FT-NMR (1H, 13C), CHN elemental analysis). In vitro antibacterial and antifungal biological evaluation and in silico molecular docking studies exhibit a profound dependence on the nature of the functionality (functionalized selenyl- /ester / acid / β-lactam) anchored to 5-(phenylcarbamoyl)pentylselenyl chain. In vitro antimicrobial studies evidenced seleno-ester 3 and trans-seleno-β-lactam 6c (incorporating p-methoxyphenyl substituents both at N1 and C4 atoms of the β-lactam ring) to be active against all tested gram positive bacterial (S. aureus, B. subtilis), gram negative bacterial (E. coli, P. aeruginosa) and fungal (C. albicans) species exhibiting 9-20 mm and 8-12 mm diameter of inhibition zones. trans-β-Lactam 6b (with C4-phenyl and N1-p-methylphenyl groups) exhibited maximum inhibition zone diameter (14 mm against S. aureus) amongst trans-6a-d. Molecular docking results of ligand binding affinity are observed to be in well agreement with the in vitro antimicrobial results making these seleno-compounds potential candidates of medicinal importance.
在此,我们揭示了双(5-苯基氨基戊基)二硒酸酯2的应用,以获得独特的硒酸酯,即2-(5-(苯基氨基戊基)戊硒基)乙醇酸3,并进一步将3转化为2-(5-(苯基氨基戊基)戊硒基)乙醇酸4。接下来,从硒酸4和取代亚胺5a-d开始,报道了具有时间效率(15分钟完成)和立体选择性的反式3-((5-苯基氨基)戊基硒基)β-内酰胺6a-d(产率52-78%)的合成,并获得了相关的表征数据(FT-IR, FT-NMR (1H, 13C), CHN元素分析)。体外抗菌和抗真菌生物学评价以及硅分子对接研究显示,在很大程度上依赖于锚定在5-(苯氨基甲酰)戊基硒基链上的功能(功能化硒基- /酯/酸/ β-内酰胺)的性质。体外抗菌研究证明,硒酸酯3和反式硒酸-β-内酰胺6c(在β-内酰胺环的N1和C4原子上结合对甲氧基苯基取代基)对所有测试的革兰氏阳性细菌(金黄色葡萄球菌、枯草芽孢杆菌)、革兰氏阴性细菌(大肠杆菌、铜绿假单胞菌)和真菌(白色念珠菌)都有活性,抑制区直径分别为9-20毫米和8-12毫米。反式-β-内酰胺6b(含c4 -苯基和n1 -对甲基苯基)对金黄色葡萄球菌的抑制带直径最大(14 mm)。观察到配体结合亲和力的分子对接结果与体外抗菌结果非常一致,使这些硒化合物具有潜在的药用价值。
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Journal of Sulfur Chemistry
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