Journal of Sulfur Chemistry最新文献

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Synthesis and biological potency of novel optically active α-(arylthio) alkanoic acid derived from amino acids 氨基酸衍生的新型光学活性α-（芳基硫代）烷酸的合成及其生物效力

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2579614

Muzaffar Kazm Kakabor , Lana Hadi Chawishli

This study focuses on the synthesis and biological evaluation of optically active α-(arylthio)alkanoic acids derived from L- and D-amino acids such as phenylalanine, valine, and leucine. A two-step synthetic pathway was used for the preparation of the compounds, which included bromination of amino acids followed by subsequent nucleophilic substitution with thiophenol or 4-bromothiophenol. Enantiomeric purity and high yields of the synthesized entities were established based on ¹H-NMR, ¹³C-NMR, FT-IR, and optical rotation. In vitro tests were performed to study the antimicrobial, antioxidant, and anticancer properties of the targeted products. Compound (18) exhibited the strongest antimicrobial activity, significantly inhibiting the growth of Staphylococcus aureus and Candida albicans, and finally, both compounds (18) and (16) showed the strongest antioxidant activity, with scavenging capabilities of 84% and 80%, respectively. In anticancer tests, compound (15) presented the best activity, inhibiting the cell viability of breast cancer (MCF7) cell lines by 60.56%. Computational docking supported the experimental findings. These results suggest potential applications of α-(arylthio)alkanoic acids as therapeutic agents for infections, oxidative stress disorders, and cancer.

本研究主要研究了从苯丙氨酸、缬氨酸和亮氨酸等L-和d -氨基酸衍生的光学活性α-（芳基硫代）烷酸的合成和生物学评价。该化合物的制备采用两步合成途径，包括氨基酸的溴化，然后用硫代酚或4-溴代硫代酚进行亲核取代。通过1H-NMR、13C-NMR、FT-IR和旋光性等手段确定了合成实体的对映体纯度和产率。体外试验研究了目标产品的抗菌、抗氧化和抗癌特性。化合物（18）的抑菌活性最强，能显著抑制金黄色葡萄球菌和白色念珠菌的生长；化合物（18）和化合物（16）的抗氧化活性最强，清除率分别为84%和80%。在抗癌试验中，化合物（15）表现出最好的活性，抑制乳腺癌（MCF7）细胞株的细胞活力为60.56%。计算对接支持实验结果。这些结果提示α-（芳基硫代）烷酸作为感染、氧化应激障碍和癌症治疗剂的潜在应用。

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引用次数: 0

A review on synthetic methodologies of thiazolo[3,4-a]quinoxalines 噻唑[3,4- A]喹诺啉类化合物合成方法综述

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2596137

Mohamed Ibrahim Hegab

The skeleton of thiazoloquinoxaline is a remarkable structural system that belongs to the thiazole ring fused with quinoxaline nucleus. Some thiazoloquinoxalines increase the diversity of certain biological properties such as antibacterial, antiviral, and antiamoebic activities. The current review article represents a survey of the literature covering the synthetic strategies leading to thiazolo[3,4-a]quinoxalines.

噻唑喹啉骨架是一个显著的结构体系，属于噻唑环与喹啉核融合。一些噻唑喹啉类药物增加了某些生物特性的多样性，如抗菌、抗病毒和抗阿米巴活性。目前的综述文章代表了文献综述，涵盖了导致噻唑[3,4-a]喹诺啉的合成策略。

引用次数: 0

Novel nosylation reagent mediated highly efficient synthesis, DFT approach and biological activities of sulfonamides 新型甲基化试剂介导的高效合成、DFT方法及磺胺类化合物的生物活性

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2582553

Ravi Kumar Shekunti , Sudharshan Reddy Akkamolla , Nagelli Kishore , Sridhar Reddy Kothakapu , Annapurna Padmavathi Devarakonda

The study reports a highly efficient, eco-friendly method using a novel reagent, N-pyridinium nosyl chloride ([DMAPNS]⁺Cl^-), for the rapid synthesis of sulfonamides under mild conditions. Equimolar reactions of the reagent with various amines in dichloromethane at room temperature were completed within 15 minutes, affording isolated yields of up to 97% without the need for chromatographic purification. Density functional theory (DFT) calculations at the B3LYP/6-311G level were performed to examine the electronic structures and reactivity of the pyridinium salts. Key quantum chemical parameters such as E_HOMO, E_LUMO, energy gap (ΔE), electron affinity (EA), ionization potential (IP), global electrophilicity index (ω), dipole moment (µ), softness (S), chemical hardness (η), and absolute electronegativity (χ) were evaluated to interpret molecular stability and reactivity trends. Among these, compound 18 exhibited the highest ionisation potential (7.84 eV) and hardness (2.05 eV), indicating enhanced chemical stability. . Antibacterial screening against selected MTCC and NCIM strains showed that compounds 4, 8, 12, 16 and 18 displayed strong broad-spectrum activity, while compounds 14, 20, and 22 exhibited moderate effects. The integration of synthetic methodology, quantum chemical analysis, and biological evaluation highlights the potential of this nosylation approach for the design of future sulfonamide-based therapeutics.

该研究报告了一种高效、环保的方法，使用一种新型试剂n -吡啶甲基氯（[DMAPNS]+Cl-），在温和条件下快速合成磺胺类药物。该试剂在室温下与各种胺在二氯甲烷中进行等摩尔反应，在15分钟内完成，分离收率高达97%，无需进行色谱纯化。在B3LYP/6-311G水平上进行密度泛函理论（DFT）计算，考察了吡啶盐的电子结构和反应性。通过评价关键的量子化学参数，如EHOMO、ELUMO、能隙（ΔE）、电子亲和性（EA）、电离势（IP）、全局亲电性指数（ω）、偶极矩（µ）、柔软度(S)、化学硬度（η）和绝对电负性（χ）来解释分子的稳定性和反应性趋势。其中化合物18具有最高的电离电位（7.84 eV）和硬度（2.05 eV），表明化合物具有较强的化学稳定性。对选定的MTCC和NCIM菌株进行抗菌筛选，化合物4、8、12、16和18表现出较强的广谱活性，而化合物14、20和22表现出中等的广谱活性。合成方法、量子化学分析和生物学评价的整合突出了这种甲基化方法在设计未来基于磺胺的治疗方法方面的潜力。

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引用次数: 0

Cooperativity in trisulfidephosphangulene triad adducts C18H9S3P(HX)(Y)1−: a theoretical study 三硫磷二烯三加合物C18H9S3P(HX)(Y)1−的协同性：理论研究

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2588168

Abdul Bari Omary , Abedien Zabardasti

A theoretical study of the model anionic triad complexes of C₁₈H₉S₃P(HX)(Y)⁻ where HX = (HF, HCl) and Y = (F⁻, Cl⁻, C≡N⁻, N≡C⁻) have been carried out using the density functional theory B3LYP(6-311++G(2d,2p)) computational methods. Four distinctive non-covalent interaction patterns, including a pnicogen bond (PnB), tetrel bond (TtB), a chalcogen bond (ChB), and a hydrogen bond (HB), were found for complex formation between trisulfidephosphangulene (C₁₈H₉S₃P) with CN⁻, NC⁻, F⁻, Cl⁻ anions, and HF, HCl neutral molecules. Each HX and Y component can interact on the apex or at basal sites of the C₁₈H₉S₃P molecule and result in C₁₈H₉S₃P(HX)_a(Y)_b⁻ or C₁₈H₉S₃P(HX)_b(Y)_a⁻ aggregates. From the anticipated models, stabilities of the C₁₈H₉S₃P(HF)_b(F)_a⁻, C₁₈H₉S₃P(HF)_a(F)_a⁻, C₁₈H₉S₃P(HF)_a(CN)_b⁻, C₁₈H₉S₃P(HF)_a(NC)_b,⁻ and C₁₈H₉S₃P(HF)_a(Cl)_b⁻ triads are greater than other types. The results show a considerable cooperative effect in obtaining triads from corresponding dyad adducts. Natural bond orbital theory (NBO) and Bader’s theory of ‘atoms in molecules’ (AIM) methods have been applied to analyze the intermolecular interactions. Strong correlations have been observed between stabilities and charge transfer (qCT) in the analyzed systems.

利用密度泛函理论B3LYP（6-311++G(2d,2p)）计算方法，对C18H9S3P(HX)(Y)−模型阴离子三元配合物进行了理论研究，其中HX = (HF, HCl)和Y = (F−,Cl−,C≡N−,N≡C−)。在三硫磷烯（C18H9S3P）与CN−、NC−、F−、Cl−阴离子和HF、HCl中性分子之间形成络合物时，发现了四种不同的非共价相互作用模式，包括PnB键、TtB键、ChB键和HB键。每种HX和Y组分可以在C18H9S3P分子的顶端或基部相互作用，导致C18H9S3P(HX)a(Y)b−或C18H9S3P(HX)b(Y)a−聚集。从预期模型来看，C18H9S3P(HF)b(F)a−、C18H9S3P(HF)a(F)a−、C18H9S3P(HF)a(CN)b−、C18H9S3P(HF)a(NC)b−和C18H9S3P(HF)a(Cl)b−三联体的稳定性大于其他类型。结果表明，从相应的二元加合物中得到三合物具有相当大的协同效应。应用自然键轨道理论（NBO）和Bader的“分子中原子”理论（AIM）方法分析了分子间相互作用。在所分析的体系中，稳定性与电荷转移（qCT）之间存在很强的相关性。

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引用次数: 0

Novel thiazole–imine hybrids: one pot and stepwise synthesis, characterization, antibacterial, antioxidant activities, and molecular docking studies 新型噻唑-亚胺杂化物：一锅和分步合成、表征、抗菌、抗氧化活性和分子对接研究

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2575780

Alaa Tofiq Ahmed , Awaz Jamil Hussein

Novel derivatives of thiazoles were developed, synthesized, and tested in terms of antioxidant and antibacterial properties, as well as in terms of molecular docking. Synthesis was done by one-pot and stepwise processes, beginning with aldehydes to produce benzyloxy intermediates, which were mixed with thiosemicarbazide and phenacyl bromide to give thiazoles. FT-IR, ¹H NMR, ¹³C NMR, and ¹³C DEPT-NMR confirmed the structures of all derivatives. The comparison of biological results showed that thiosemicarbazones 4a (IC50 = 1.62 µM) and 4b (IC50 = 1.89 µM) were the most active, and thiazole 6b (IC50 = 14.63 µM) was the least active one. Thiosemicarbazone derivatives showed considerable activity, with 5b and 5c showing the biggest inhibition areas on Escherichia coli and Staphylococcus aureus as an indicator of antibacterial activity. PDB: 1QSG In molecular docking experiments, the lead thiazole compounds were observed to bind well in the FabI active site, with binding energies of −9.8 and −9.6 kcal/mol, respectively, indicating that the interactions between the thiazole compounds and the active site were stable through hydrogen bonding and hydrophobic interactions. Altogether, these findings demonstrate the therapeutic advantages of thiazole-based heterocyclic hybrids as lead molecules in the creation of novel antioxidants and antibacterial agents.

开发、合成了新型噻唑衍生物，并对其抗氧化、抗菌性能和分子对接性能进行了测试。通过一锅分步合成，从醛类开始生产苯氧基中间体，与硫代氨基脲和苯氧基溴混合得到噻唑。FT-IR，¹H NMR， 13C NMR和13C DEPT-NMR证实了所有衍生物的结构。生物学结果比较表明，硫代氨基脲酮4a （IC50 = 1.62µM）和4b （IC50 = 1.89µM）活性最高，噻唑6b （IC50 = 14.63µM）活性最低。硫代氨基脲衍生物显示出相当大的活性，其中5b和5c对大肠杆菌和金黄色葡萄球菌的抑制面积最大，这是抗菌活性的指标。在分子对接实验中，观察到噻唑类先导化合物在FabI活性位点结合良好，结合能分别为- 9.8和- 9.6 kcal/mol，表明噻唑类化合物通过氢键和疏水相互作用与活性位点的相互作用稳定。总之，这些发现证明了噻唑类杂环杂环化合物作为先导分子在创造新型抗氧化剂和抗菌剂方面的治疗优势。

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引用次数: 0

Tetrabutylammonium iodide-catalyzed synthesis and anticancer screening of 2-thioxoimidazolidine-4,5-dione: a comparative theoretical and experimental approach 四丁基碘化铵催化2-硫代咪唑烷-4,5-二酮的合成与抗癌筛选：理论与实验的比较

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2574910

Nitin Srivastava , Amit K Chaturvedi , Anant Ram , Poonam Rawat , Ram Kishore , R. N. Singh , Devdutt Chaturvedi

Cancer is one of the leading global diseases responsible for morbidity and mortality of humankind. According to the WHO report, one in 5 people worldwide will develop cancer during their lifetime. So, there is a need for the development of new and effective chemotherapeutic drugs. This research reports an optimized, simple, effective, environment-friendly tetrabutylammonium iodide (TBAI) peddled synthetic protocol for 2–thioxoimidazolidine-4,5-diones (9a-9i) using readily available, less expensive, and least harmful chemicals at room temperature. The synthesized compounds were further studied for the mechanism of the apoptosis induced in HCT-15 (colon cancer), U87-MG (brain cancer) and HeLa (Cervical cancer) cells based on in-silico and in-vitro approaches. The computational study was conducted at the B3LYP/6-311G (d, p) basis set for analyzing molecular geometry, conformation, stability, and molecular electrostatics potential surface (MEPS). In silico study of the interactions of these compounds (9a-9i) and target proteins 5I9B, 6EB5, and 4DK5 of HeLa, HCT-15, and U87-MG, respectively, has been very promising in deactivating the protein synthesis in cancer cells. These compounds may further be developed as effective chemotherapeutics.

癌症是造成人类发病率和死亡率的主要全球性疾病之一。根据世界卫生组织的报告，全球五分之一的人会在一生中患上癌症。因此，有必要开发新的有效的化疗药物。本研究报告了一种优化、简单、有效、环保的四丁基碘化铵（TBAI）合成方案，该方案使用易于获得、价格较低、危害最小的室温化学物质合成2 -硫代咪唑烷-4,5-二酮（9a-9i）。基于硅内和体外方法进一步研究合成的化合物对HCT-15（结肠癌）、U87-MG（脑癌）和HeLa（宫颈癌）细胞诱导凋亡的机制。计算研究是在B3LYP/6-311G （d, p）基集上进行的，用于分析分子几何形状、构象、稳定性和分子静电势面（MEPS）。这些化合物（9a-9i）分别与HeLa、HCT-15和U87-MG的靶蛋白5I9B、6EB5和4DK5相互作用的计算机研究，在使癌细胞中蛋白质合成失活方面非常有希望。这些化合物可以进一步开发为有效的化疗药物。

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引用次数: 0

On the reaction of N,N-diaryl-substituted 2-aminothiophenes with thionyl chloride – formation and structural characterization of 9-aryl-9H-benzo[b]thieno[2,3-e][1,4]thiazine-2-carboxylates N，N-二芳基取代的2-氨基噻吩与亚硫酰氯的反应-9 -芳基- 9h -苯并[b]噻吩[2,3-e][1,4]噻嗪-2-羧酸盐的生成与结构表征

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2593646

Evgenia Dmitrieva , Susanne Machill , Horst Hartmann

By reaction of thionyl chloride with N,N-diaryl-substituted 2-aminothiophenes, depending on their substitution pattern, 2,2′-diamino-3,3′-bithiophenes or 9-aryl-9H-benzo[b]thieno[2,3-e][1,4]thiazines were formed. Their structures were confirmed by means of mass spectrometry and NMR spectroscopy and characterized by cyclovoltammetry and ultraviolet–visible-near infrared (UV–vis–NIR) spectroscopy. The radical cations generated by electrochemical oxidation of the compounds were studied by in situ electron paramagnetic resonance (EPR)/UV–vis–NIR spectroelectrochemistry. Reactions of N,N-substituted 2-aminothiophenes with thionyl chloride yield oxidation products that differ significantly in structure and properties compared to those produced by electrochemical oxidation.

亚硫酰氯与N，N-二芳基取代的2-氨基噻吩反应，根据取代构型的不同，生成2,2 ' -二氨基-3,3 ' -双噻吩或9-芳基- 9h -苯并[b]噻吩[2,3-e][1,4]噻吩。用质谱法和核磁共振谱法对其结构进行了确证，并用环伏安法和紫外-可见-近红外光谱法对其进行了表征。采用原位电子顺磁共振(EPR)/紫外-可见-近红外（UV-vis-NIR）光谱电化学方法研究了化合物电化学氧化生成的自由基阳离子。N，N取代的2-氨基噻吩与亚硫酰氯反应生成的氧化产物在结构和性能上与电化学氧化产物有很大不同。

引用次数: 0

Catalyst free, three components synthesis of new 2-(1,3-dithiol-2-ylidene)malononitrile and 2-(thiazol-2-ylidene)malononitrile from nitroepoxides and malononitrile-heterocumulene adducts 无催化剂，三组分合成新的2-（1,3-二硫醇-2-乙基）丙二腈和2-（噻唑-2-乙基）丙二腈

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2577150

Manijeh Nematpour

In this study, a one-pot, catalyst-free, and three-component reaction was developed to synthesize various novel 2-(1,3-dithiol-2-ylidene)malononitrile and 2-(thiazol-2-ylidene)malononitrile derivatives at room temperature in good yields. The reaction was carried out via the formation of malononitrile-heterocumulene (carbon disulfide or isothiocyanate) adducts, followed by the addition of nitroepoxide as an efficient starting material to synthesize the products with easy purification. In this process, 15 new heterocyclic compounds from the 1,3-dithiole and thiazole family were synthesized and identified by NMR, Mass, and IR analyses.

在本研究中，建立了一锅、无催化剂、三组分的反应，在室温下合成了多种新型的2-（1,3-二硫醇-2-基二烯）丙二腈和2-（噻唑-2-基二烯）丙二腈衍生物，收率较高。该反应是通过生成丙二腈-异硫脲（二硫化碳或异硫氰酸酯）加合物，然后加入硝基环氧化物作为高效的起始原料，合成了易于纯化的产品。在此过程中，共合成了15个新的1,3-二噻唑和噻唑类杂环化合物，并通过NMR、Mass和IR分析对其进行了鉴定。

引用次数: 0

Na2S•9H2O/DABCO/H2O: a metal-free system for chemoselective reduction of chalcones Na2S•9H2O/DABCO/H2O：用于查尔酮化学选择性还原的无金属体系

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2604043

Xiao Tan , Xiang-Ting Zheng , Jun-Feng He , Jin-Ke Tan , Ning Kang , Yun-Zhu Liu , Zhen-Shen Ouyang , Ye-Ding Zhao , Cai-Yun Peng , Rong-Geng Fu

A simple and practical approach to access dihydrochalcones from chalcones via a Na₂S•9H₂O/DABCO/H₂O system in DMF is reported. This new reduction system exhibits wide functional group tolerance and activity in the reduction of chalcones by utilizing water as a cost-effective, safe and environmentally friendly hydrogen donor. The mechanism describes the reaction pathway was also discussed.

报道了一种在DMF中通过Na2S•9H2O/DABCO/H2O体系从查尔酮中获得二氢查尔酮的简单实用方法。这种新的还原体系在还原查尔酮方面表现出广泛的官能团耐受性和活性，利用水作为一种经济、安全、环保的氢供体。讨论了反应途径的机理。

引用次数: 0

Unraveling Monothioavobenzones as a chemical UVAI filter 解开单硫阿伏苯宗作为化学UVAI过滤器

IF 1.6 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry

Pub Date : 2026-01-02 DOI: 10.1080/17415993.2025.2571657

Deepak Kumar Sahoo , Sachin Mallikarjun More , Konkallu Hanumae Gowd

Avobenzone is a versatile dibenzoyl methane-based chemical UVA filter and loses its activity upon exposure to UV radiation/sunlight. It loses its UVA filtering activity due to photoinduced tautomerization from keto–enol to diketo form. Monothiodibenzoylmethane has exhibited photochemical transformation between thione-enol to keto-thiol form instead of thione-keto form. Such transformation in monothioavobenzones would be beneficial, provided thione-enol and keto-thiol forms have absorbance in the UVA region (315-400 nm). Using the computational platform working on density functional theory (DFT), the current report computes the physicochemical properties of monothioavobenzones and compares them with those of avobenzone/dithioavobenzone. The UV spectra were computed using TD-DFT with B3LYP-D3 functional and 6-31G** basis set. The activation energy barrier for tautomerization was computed using AutoTS. The bond dissociation energy for Norrish Type-I clevages was achieved using B3LYP functional with LACV3P** basis set. Monothioavobenzones differ from native avobenzone and dithioavobenzone, having broad UVA absorbance, stabilizing non-chelated enethiol forms, and increased bond dissociation energy for potential Norrish Type-I cleavages. These studies demonstrate that monothioavobenzones are a unique chemical UVAI filter that may be useful for cosmetics.

Abbreviations: AutoTS: auto transition state; BDE: bond dissociation energy; MTDBM: monothiodibenzoylmethane

阿伏苯宗是一种多功能的二苯甲酰甲烷基化学UVA过滤器，暴露在紫外线辐射/阳光下会失去活性。由于光诱导从酮烯醇到双酮醇的互变异构，它失去了过滤UVA的活性。单硫代二苯甲酰甲烷在硫酮-烯醇而不是硫酮-酮之间发生光化学转化。如果硫烯醇和酮硫醇形式在UVA区域（315-400 nm）具有吸光度，那么单硫代阿伏苯酮类化合物中的这种转化是有益的。利用密度泛函理论（DFT）的计算平台，本报告计算了单硫代阿伏苯宗的物理化学性质，并将其与阿伏苯宗/二硫代阿伏苯宗进行了比较。采用B3LYP-D3泛函和6-31G**基集的TD-DFT计算紫外光谱。利用AutoTS计算了异构化的活化能垒。利用B3LYP泛函和LACV3P**基集获得了Norrish Type-I型裂缝的键解离能。单硫代阿伏苯酮不同于天然的阿伏苯酮和二硫代阿伏苯酮，它具有广泛的UVA吸光度，稳定非螯合的烯硫醇形式，并且增加了潜在的诺里什i型裂解的键解离能。这些研究表明，单硫代阿伏苯宗是一种独特的化学UVAI过滤器，可能对化妆品有用。AutoTS：自动过渡状态；BDE：键解离能；MTDBM: monothiodibenzoylmethane

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