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POLYMERS FOR ADVANCED TECHNOLOGIES · 2017 ·Vol. 29 ·期 3 ·1030-1038 · IF 1.907

Preparation and characterization of polyphenylene sulfide–based chelating resin–functionalized 2-amino-1,3,4-thiadiazole for selective removal Hg(II) from aqueous solutions

Gonglei Shao,Junfeng Xiao,Zhihong Tian,Jiajia Huang,Siguo Yuan

A novel chelating resin (PPS-ATD) containing N and S elements was prepared through the chloromethylation of polyphenylene sulfide resin and subsequent functionalization with 2-amino-1,3,4-thiadiazole (ATD). The structure of PPS-ATD was systematically characterized and analyzed by the Fourier transform infrared spectroscopy, elemental analysis, thermogravimetric analysis, scanning electron microscope, and energy dispersive spectrometer. The adsorption performance of PPS-ATD was evaluated by batch methods at different pH, temperature, adsorption time, and initial concentration, and the results showed that the PPS-ATD exhibited high adsorption capacity (197.79 mg·g −1 at 298 K) and selectivity for Hg(II). The adsorption of PPS-ATD for Hg(II) was well fitted by the Langmuir isotherm model, and the adsorption process was endothermic. After 5 consecutive regeneration cycles, no obvious loss in the adsorption capacity of the PPS-ATD was found, which implied that the PPS-ATD had great application prospects in the treatment of mercury-containing wastewater.

研究领域: 环境科学 · 材料科学
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FOOD CHEMISTRY · 2025 · IF 9.8

1,3,4-Thiadiazole and quinolinone based multifunctional probes for fluorescence turn-on and colorimetric monitoring of Al3+ and Fe3+ in food and aqueous environment applications

Jinwei Tian,Yao Wei,Chengwei Lü

To achieve the development of fluorescence turn-on probe and dual detection of Al 3+ and Fe 3+ , three organic molecules (named KN , KP and KS ) were synthesized based on quinolinone, Schiff base, 1,3,4-thiadiazole or benzothiazole units. Their fluorescence characteristics and response mechanism were investigated thoroughly. The recognition process created obvious color change under sunlight and nearly 30 to 66 folds fluorescence enhancement under ultraviolet light. The formation of stable complexes leads to inhibition of intramolecular charge transfer, restriction of imine isomerization and consequent optical behaviors. For KN , Al 3+ and Fe 3+ could be distinguished via different UV–vis response or by using masking agent with detection limits of 0.18 μM and 0.20 μM, respectively. Another satisfactory result for distinguishing two ions was achieved with KS under pH = 2 or 10 condition. More importantly, KN and KS were successfully used to detect Al 3+ or Fe 3+ in foods, water samples and pharmaceutical products.

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RSC Advances · 2025 ·Vol. 15 ·期 34 ·28084-28092 · IF 4.6

Design, synthesis, and antimicrobial evaluation of novel 1,2,4-trizaole thioether derivatives with a 1,3,4-thiadiazole skeleton

Yangming Jiang,Jiansong An,Yu Xia,Qiang Fei,Daoping Wang,Yang Lu,Wenneng Wu

The aim of this study was to design and synthesize 17 novel 1,2,4-triazole thioether derivatives containing 1,3,4-thiadiazole thioether. Bioactivity assays indicated that several target compounds exhibited moderate to good antifungal and antibacterial activities. Notably, compound 9d demonstrated significantly stronger antifungal activity against Trichoderma sp. in Morchella esculenta (TSM) and Mucor sp. in Dictyophora rubrovalvata (MSD), with EC50 values of 9.25 and 12.95 μg mL−1, respectively, compared to the commercial fungicide pyrimethanil, which had EC50 values of 35.29 and 15.51 μg mL−1. Furthermore, compound 9d found to have strong antibacterial activity against Pseudomonas syringae pv. actinidiae (PSA) in vitro, with an EC50 of 9.34 μg mL−1, markedly superior to that of thiodiazole copper (81.74 μg mL−1). Additionally, the in vivo anti-PSA assessment revealed therapeutic and protective activities at 200 μg mL−1 of 59.39% and 79.33%, respectively, outperforming thiodiazole copper (38.91% and 67.64%, respectively). According to molecular docking simulations the interaction between compound 9d and FtsZ was mainly due to hydrogen bond formations with GLU-296, ARG-301, LYS-188, ASP-29 and GLY-30. This report suggests that these novel 1,2,4-triazole thioether derivatives featuring a 1,3,4-thiadiazole skeleton may effectively mitigate fungal and bacterial threats to plants.

研究领域: 药物化学 · 微生物学 · 植物病理学 · 生物有机化学 · 分子生物学
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Materials Science & Engineering C-Materials for Biological Applications · 2013 · IF 2.404

Bismuth (III) PVC membrane ion selective electrodes based on two compounds: Acylhydrazone and thiosemicarbazone with 1,3,4-thiadiazole

Zhenning Yan,Shuangqiang Wang,Haixia Wang,Shuangyan Wu

Two Bi 3   + selective electrodes based on L1 and L2 incorporated into a polyvinylchloride (PVC) membrane have been developed. The ionophores L1 and L2 are 2-(5-amino-1,3,4-thiadiazol-2-ylthio)-N′-benzylidene acetohydrazone and 1-(2-(5-amino-1,3,4-thiadiazol-2-ylthio) acetyl)-4-benzoylthiosemicarbazone, respectively. These electrodes are composed of dioctylphtalate (DOP) as a plasticizer and sodium tetraphenylborate (NaTPB) as the lipophilic additive. The best performance was obtained with the membrane compositions of L1 (0.30): PVC (33.22): DOP (66.36): NaTPB (0.12) (%, w/w) and L2 (1.00): PVC (33.00): DOP (65.91): NaTPB (0.09) (%, w/w). Two membrane electrodes show Nernstian response slopes towards Bi 3   + (20.2 and 19.7   mV/decade, respectively) over the concentration range of 10 −   7 –10 −   3 and 10 −   7 –10 −   2   M, respectively. The effects of the pH and the possible interfering cations were investigated. Both electrodes have a response time of about 10   s, and they can work in a certain concentration aqueous ethanol solution. The prepared electrodes were used as an indicator electrode in potentiometric titration of Bi 3   + ions with EDTA. The membrane sensors were also applied to the determination of Bi 3   + content in compound bismuth aluminate tablets.

研究领域: 分析化学 · 材料科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Discovery of Novel Antibacterial Agents against Plant Pathogens: Design, Synthesis, Antibacterial Activity, and Mechanism of Action of 1,2,4-Thiadiazole Derivatives Containing a Sulfone Moiety

Yue Zou,Mei Zhu,Zongnan Zhu,Tingting Du,Xing Liu,Yaojia Jiang,Jixiang Chen

1,2,4-Thiadiazole derivatives containing a sulfone moiety were designed and synthesized via scaffold hopping to facilitate the discovery of novel antibacterial agents. Most of the compounds exhibited excellent activity against three plant pathogenic bacteria. The half-maximal effective concentrations (EC50) of compound B7 for Xanthomonas oryzae pv oryzae (Xoo) and X. oryzae pv oryzicola (Xoc) concentrations were 0.4 and 1.0 mg/L, respectively. In addition, the EC50 values of compounds B1 and B24 for Xoo, Xoc, and Pseudomonas syringae pv actinidiae (Psa) were less than 5 mg/L and significantly better than those of the positive control agents thiodiazole copper (121.8, 119.5, and 142.0 mg/L, respectively) and bismerthiazol (73.3, 65.6, and 128.8 mg/L, respectively). Compound B7 exhibited protective and curative activities of 48.1 and 46.7%, respectively, against bacterial leaf blight, which were higher than those of bismerthiazol (35.5 and 36.9%, respectively) and thiodiazole copper (39.3 and 39.5%, respectively). Additionally, compound B7 exerted an effect on the virulence factors of Xoo (production of exopolysaccharides and extracellular enzymes, biofilm formation, and motility), membrane permeability, cell surface morphology, and intracellular content of reactive oxygen species. Transcriptome analysis showed that compound B7 improved the resistance of rice plants to external stress by influencing the metabolic process, biological regulation, catalytic activity of enzymes, and plant–pathogen interaction. Compound B7 can therefore be considered as a potential candidate antibacterial agent and warrants an in-depth investigation in the future.

研究领域: 植物病理学 · 药理学 · 分子生物学
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Inorganic and Nano-Metal Chemistry · 2017 · IF 0

Synthesis, crystal structures, and biological activity of zinc(II) complexes derived from 2-amino-1,3,4-thiadiazole derivatives

Hui-Long Zhu,Yu-Wei Liu,Zong-Ming Tang,Fu-Jun Yin,Wei-Wei Liu,Zhi-Ling Cao,Juan Bao,Meng Li,Ling-Yan Qin,Da-Hua Shi

Two new similar zinc(II) complexes, [ZnCl2L12] and [ZnCl2L22], derived from the 2-amino-1,3,4-thiadiazole derivatives, were prepared and structurally characterized by X-ray diffraction. The Zn atom in each complex has a tetrahedral coordination and is coordinated by two N atoms of the ligands and two Cl atoms. The urease inhibitory activities of the complexes and the ligands were evaluated.

CAS / MDL: 2444-36-2 104-03-0
研究领域: 配位化学 · 生物无机化学 · 药物化学
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HETEROATOM CHEMISTRY · 2014 ·Vol. 26 ·期 2 ·142-149 · IF 1.257

Synthesis, Bioactivity, and the Anion-Binding Property of 2-Sulfydryl-1,3,4-thiodiazole Derivatives

Xuefang Shang,Wanli Li,Xiaofang Wei,Huanle Zhang,Zhiyuan Fu,Jinlian Zhang,Xiufang Xu

Two new compounds ( 1 and 2 ) containing 2-sulfydryl-1,3,4-thiodiazole have been synthesized and optimized. They both showed wide antibacterial activity for colon bacillus, Staphylococcus aureus , S. albus , dysentery bacillus and inferior activity for Bacillus subtilis . In addition, their binding properties were evaluated for biologically important anions (F – , Cl – , Br – , I – , AcO – , and H 2 PO 4 – ) by theoretical investigation, UV–vis, fluorescence, and 1 H NMR titration experiments, and they displayed strong binding ability for H 2 PO 4 – without the interference of other anions tested. Especially the binding ability of compound 2 containing anthracene with H 2 PO 4 – was 1000 times stronger than that of compound 1 containing nitrobenzene. Two compounds based on 2-sulfydryl-1,3,4-thiodiazole have both properties of anion recognition and antibacterial activity.

研究领域: 有机化学 · 药物化学 · 化学生物学
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ChemMedChem · 2021 ·Vol. 16 ·期 15 ·2354-2365 · IF 3.466

Synthesis and Antimicrobial Activity Evaluation of Imidazole-Fused Imidazo[2,1-b][1,3,4]thiadiazole Analogues

Fang Yan Guo,Chang Ji Zheng,Meiyuan Wang,Jiangping Ai,Lan Ying Han,Liu Yang,Ye Fang Lu,Yu Xuan Yang,Ming Guan Piao,Hu-Ri Piao,Chun-Mei Jin,Cheng Hua Jin

Graphical Treating fungal infection : A series of imidazole fused imidazo[2,1- b ][1,3,4]thiadiazoles were synthesized as potent, selective inhibitors of fungal for Candida albicans reduced chronic dermatomucoso candidiasis. The most potent compound, 21 a , showed druglike properties with low cytotoxicity and hemolysis. Three series of new imidazole-fused imidazo[2,1- b ][1,3,4]thiadiazole analogues (compounds 20 a – g , 21 a – g , and 22 a – g ) have been synthesized, and their antibacterial and antifungal activities have been evaluated. All the target compounds showed strong antifungal activity and high selectivity for the test fungus Candida albicans over Gram-positive and -negative bacteria. N -((4-(2-Cyclopropyl-6-(4-fluorophenyl)imidazo[2,1- b ][1,3,4]thiadiazol-5-yl)-5-(6-methyl-pyridin-2-yl)-1 H -imidazol-2-yl)methyl)aniline ( 21 a ) showed the highest activity against C. albicans (MIC 50 =0.16 μg/mL), 13 and three times that of the positive control compounds gatifloxacin and fluconazole, respectively. Compounds 21 a and 20 e did not show cytotoxicity against human foreskin fibroblast-1 cells, and compound 21 a was as safe as the positive control compounds in hemolysis tests. These results strongly suggest that some of the compounds produced in this work have value for development as antifungal agents.

研究领域: 药理学 · 微生物学
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JOURNAL OF HAZARDOUS MATERIALS · 2019 · IF 7.65

Post-functionalization of UiO-66-NH2 by 2,5-Dimercapto-1,3,4-thiadiazole for the high efficient removal of Hg(II) in water

Likang Fu,Shixing Wang,Guo Lin,Libo Zhang,Qiming Liu,Ju Fang,Chenhuinan Wei,Gang Liu

A new MOFs adsorbent was prepared by post-functionalization of UiO-66-NH 2 with 2,5-Dimercapto-1,3,4-thiadiazole and utilized to remove the Hg(II) in water selectively. The UiO-66-types were detected by Fourier transform infrared spectroscopy (FTIR), field emission scanning electron microscope (FESEM), Brunauer-Emmett-Teller (BET) and zeta potential instruments. The adsorption properties of the new MOFs adsorbent were investigated by batch experiments. The actual maximum adsorption amount was 670.5 mg/g at the optimal pH of 3. Adsorption kinetic and isotherm models were exceedingly fitted to pseudo-second-order and Langmuir/Dubinin-Radushkevich, respectively. The adsorption process and mode were geared to monolayer and chemisorption, the removal rate was directly proportional to the square of mercury ions concentration. The UiO-66-DMTD adsorbent was easy to be regenerated and the removal rate decreased by only 13.5% after ten consecutive cycles. The results of FTIR, XRD and XPS suggested that the adsorption mechanism lay on the complexation reaction between Hg(II) and thiol/nitrogen-containing groups. Moreover, compared with other competitive metal ions, viz., Zn(II), Co(IV), Ni(II), Cd(II), Mg(II), Fe(III), Ca(II) and Cu(II), the UiO-66-DMTD demonstrated an outstanding selective adsorption for Hg(II). These results manifested that the UiO-66-DMTD was a latent adsorbent for the efficient and selective removal of Hg(II) in wastewater.

研究领域: 环境科学 · 材料科学
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APPLIED SURFACE SCIENCE · 2020 · IF 6.182

Adsorption behavior and mechanism of Hg (II) on a porous core-shell copper hydroxy sulfate@MOF composite

Ling Zhang,Jinghua Zhang,Xinglin Li,Cuijie Wang,Ajuan Yu,Shusheng Zhang,Gangfeng Ouyang,Yuanyuan Cui

Herein, a porous core-shell copper hydroxy sulfate@metal-organic framework decorated by 2,5-dimercapto-1,3,4-thiadiazol (DMTZ) was synthesized via a facile self-template strategy for the capture of Hg 2+ . The strategy of assembling MOF shell on copper hydroxy sulfate (CHS) core avoided the self-nucleation of MOF(Cu 3 (BTC) 2 ) in the solution and complex multistep procedures by means of in situ transformation the metal source CHS into well-defined Cu 3 (BTC) 2 crystal. The structure and properties of the DMTZ modified CHS@Cu 3 (BTC) 2 (CHS@Cu 3 (BTC) 2 -DMTZ) was characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA) and N 2 sorption–desorption isotherms (BET). The adsorption behavior followed Langmuir adsorption model and the maximum adsorption capacities for the removal of Hg 2+ was up to 627.6 mg g −1 . 99.96% Hg 2+ was rapidly captured by CHS@Cu 3 (BTC) 2 -DMTZ within 10 min from 40 mg L -1 to 0.014 mg L -1 . Meanwhile, not only X-ray photoelectron spectroscopy (XPS) but also Raman spectra verified the selective and strong interaction between Hg 2+ and thiol/nitrogen-containing functional groups of DMTZ on CHS@Cu 3 (BTC) 2 -DMTZ. These results manifested that this novel thiol-functionalized MOF adsorbent had superior adsorption capacity and selective for Hg 2+ .

研究领域: 环境科学 · 材料科学
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2025 · IF 2.1

Investigation on 2-Mercapto-5-methyl-1,3,4-thiadiazole Solubility in Twelve Kinds of Organic Monosolvents Based on Models, Thermodynamic Analysis, and Solvent Effect

Yaqi Han,Fumin Xue,Wenguo Xing,Huanhuan Yin,Xiangchuan Wang,Shuai Yu

Solid–liquid equilibrium solubilities of 2-mercapto-5-methyl-1,3,4-thiadiazole (MMTD) in 12 kinds of monosolvents (i.e., methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, ethyl formate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and amyl acetate) were determined by a gravimetric method with the temperature range from 283.15 to 323.15 K. In alcoholic solvents, the solubility order is ethanol > methanol > n-propanol > i-propanol > n-butanol > i-butanol. In ester solvents, the solubility of MMTD ranking is methyl acetate > ethyl acetate > propyl acetate > butyl acetate > amyl acetate > ethyl formate. The solubility of MMTD increased with increasing temperature. Four thermodynamic models (i.e., the modified Apelblat model, the λh model, the Wilson model, and the Jouyban model) were selected to correlate the solubility data. The RAD and RMSD values were less than 0.0254 and 0.000536, respectively. The Wilson model had the best-fitting effect. The KAT-LSER model and Hansen solubility parameters were used to explain the solvent effect in this work. The Hirshfeld surface, molecular electrostatic potential surface, and free energy of solvation were used to explain the interactions between molecules. Dissolution properties of MMTD were calculated by the Wilson model. The dissolution process of MMTD is endothermic, entropy driven, and spontaneous.

CAS / MDL: 29490-19-5
研究领域: 化学工程 · 物理化学
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JOURNAL OF CHEMICAL RESEARCH · 2017 · IF 0.646

Synthesis and Evaluation of 5-Benzyl-1,3,4-Thiadiazole Derivatives as Acetylcholinesterase Inhibitors

Da-Hua Shi,Hui-Long Zhu,Yu-Wei Liu,Zong-Ming Tang,Chen Lu,Xiao-Dong Ma,Xiao-Kai Song,Wei-Wei Liu,Tong Dong,Meng-Qiu Song

Three novel 5-benzyl-1,3,4-thiadiazole derivatives were synthesised starting from phenylacetic acid derivatives. These compounds were characterised by NMR, HRMS and single-crystal X-ray diffraction analysis. 2-Pyrrolidyl-5-[2-(4-bromophenyl)methyl]-1,3,4-thiadiazole showed moderate acetylcholinesterase-inhibition activity with a 50% inhibitory concentration value of 33.16 μM. 2-Pyrrolidyl-5-[2-(4-bromophenyl)methyl]-1,3,4-thiadiazole and acetylcholinesterase docking was demonstrated using the Molecular Operating Environment program.

研究领域: 药物化学 · 神经生物学 · 有机化学
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