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Chinese Chemical Letters 2020年第2期31卷 434-438页

作者： Jun Shi Na Luo Muhan Ding Xiaoping Bao State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationCenter for Research and Development of Fine ChemicalsGuizhou UniversityGuiyang 550025China

A series of structurally novel 1,3,4-oxadiazole Thioether derivatives(6a-6z) containing a 6-fluoroquinazolinylpiperidinyl moiety were designed and synthesized using pharmacophore hybrid approach,and their structures were fully characterized by ^1H NMR,^(13)C NMR and HRMS spectra.Among them,the structure of compound 6 d was further corroborated via single-crystal X-ray diffraction analysis.In vitro antibacterial bioassays showed that compounds 6 a,6 g,6 u and 6 v possessed EC_(50) values of 30.4,30.6,27.5 and 26.0 μg/mL against phytopathogenic bacterium Xanthomonas oryzae pv.oryzae,respectively,which were significantly superior to that of commercially-available bactericide Bismerthiazol(85.1 μg/mL).Moreover,in vitro antifungal bioassays indicated that seven compounds demonstrated broad-spectrum fungicidal acitivties against six types of phytopathogenic fungi at 50 μg/mL.The present work showed the potential of 1,3,4-oxadiazole Thioether derivatives carrying a 6-fluoroquinazolinylpiperidinyl moiety as effective antimicrobial agents for crop protection,deserving further investigations in the future.

关键词： 1,3,4-Oxadiazole Thioether Fluoroquinazolinylpiperidinyl Synthesis Antibacterial activity Antifungal activity

Upper-rim-modified Thioether thiacalix[4]arene used for liquid-liquid extraction of Au(Ⅲ)and Pd(Ⅱ)in hydrochloric acid medium

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Chinese Journal of Chemical Engineering 2024年第2期66卷 110-118页

作者： Sheng Wan Rong Xie Jianhong Fan Kewen Tang Department of Chemistry and Chemical Engineering Hunan Institute of Science and TechnologyYueyang 414006China

Gold(Au)and palladium(Pd)play an increasing role in the production and human life;Therefore,it is of great significance to study their recovery.A 5,11,17,23-tetra-ethylthio-25,26,27,28-tetra-hydroxyl thiacalix[4]arene(TCAET)was synthesized specifically for the capture of Au(Ⅲ)and Pd(Ⅱ)from HCl medium by liquid-liquid extraction.In a 0.1 mol·L^(-1)HCl medium,the transfer of Au(Ⅲ)and Pd(Ⅱ)from the aqueous phase to the organic phase was highly efficient,with a transfer ratio of 100%for Au(Ⅲ)and 98%for Pd(Ⅱ).Furthermore,the extraction equilibrium time for Au(Ⅲ)was just 5 min.Job's method data demonstrated that TCAET formed complexes with Au(Ⅲ)and Pd(Ⅱ)in a ratio of 2:3 and 1:1,respectively,during the extraction process.TCAET showed high selectivity toward Pd(Ⅱ)and Au(Ⅲ)over other competing metal ions.Moreover,both Au(Ⅲ)and Pd(Ⅱ)could be successfully stripped from the loaded organic phases with a 1.0 mol·L^(-1)thiourea in 0.5 mol·L^(-1)HCl and 0.5 mol·L^(-1)thiourea in 0.5 mol·L^(-1)HCl,respectively.Results obtained from five consecutive extraction-stripping cycles showed good reusability of TCAET toward Au(Ⅲ)and Pd(Ⅱ)recovery.The conclusion can provide a certain reference for thiacalixarene in the recovery of precious metal species.

关键词： Thiacalixarene Upper-rim modification Liquid-liquid extraction Precious metal Thioether

Synthesis of core-shell structured polymers with inserted Thioether from a multi-functional scaffold

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Chinese Chemical Letters 2007年第6期18卷 758-761页

作者： Pu, Hong Ting Zhou, Qing Wan, De Cheng Tongji Univ Sch Mat Sci & Engn Inst Funct Polymers Shanghai 200092 Peoples R China

The synthesis of a Thioether inserted, core-shell structured polymer from the scaffold of hyperbranched polyglycerol (PG) was described. PG was first allyl functionalized, and in the presence of AlBN, the allyl groups further underwent radical addition to thiol compounds, thus thiol functional polyethylene oxide monomether (MPEO) were grafted onto PG. Similarly, 2-mercaptoethylammonium chloride was introduced onto PG via thiol addition, and the residual amino groups were further quaternized with decyl bromide, leading to an amphiphilic core-shell structure polymer. (c) 2007 De Cheng Wan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

关键词： core-shell scaffold Thioether radical addition hyperbranched polymer

Synthesis and Biological Activity of Myrtenal-Based Triazole-Thioether Compounds

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Synthesis and Biological Activity of Myrtenal-Based Triazole...

Recent advances in directα-C(sp^(3))-H bond functionalization of Thioethers

中国化学会全国第十二届有机合成化学学术研讨会

作者： Lin,Gui-Shan Duan,Wen-Gui Cen,Bo Yang,Lin-Xiao Li,Jia-He School of Chemistry and Chemical Engineering Guangxi University

Turpentine oil,known as a forest product from pine trees,is a renewable and abundant raw material in the world.Its dominant constituent is α-pinene.Due to the broad bioactivities of α-pinene,synthesis of α-pinene-based bioactive compounds has become an important aspect in the development and utilization of turpentine oil.[1-6] In this work,a series of novel myrtenal-based 1,2,4-triazole-Thioether compounds were designed and synthesized by a multiple-step procedure using α-pinene as starting material.The preliminary bioassay showed that some of the target compounds exhibited prominent growth inhibition activity of greater than 80.0%（A-class activity level） against root of rape（Brassica campestris）,which was better than that of the commercial herbicide flumioxazin used as the positive control.Meanwhile,some of the target compounds showed a certain antifungal activity against the tested fungi.

关键词： myrtenal triazole Thioether synthesis biological activity

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2022年第3期3卷 203-211页

作者： Long Tang Qingyue Hu Ke Yang Mazen Elsaid Chong Liu Haibo Ge Institute of Chemical Industry of Forest Products Chinese Academy of ForestryNanjing 210042China Jiangsu Key Laboratory of Advanced Catalytic Materials&Technology School of Petrochemical EngineeringChangzhou UniversityChangzhou 213164China Department of Chemistry and Biochemistry Texas Tech UniversityLubbock TX 79409USA

Thioether skeletons are widely present in drugs,natural products,functional materials,and life science.In the past decade,the selective C–H functionalization of Thioethers has been extensively studied to construct novel Thioether derivatives.This mini-review systematically introduces the recent advances in the field of the directα-C(sp^(3))-H functionalization of Thioethers.

关键词： Thioether C(sp^(3))-H bond Functionalization Photochemistry Electrochemistry Organic synthesis

Synthesis of polypeptide bearing 1,4-dithiane pendants for ROS-responsive drug release

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Chinese Chemical Letters 2020年第5期31卷 1129-1132页

作者： Tianhui Zhang Jiuxu Yao Jiamei Tian Mingxiao Deng Xiuli Zhuang Chunsheng Xiao Key Laboratory of Polymer Ecomaterials Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China University of Science and Technology of China.Hefei 230026 China Department of Chemistry.Northeast Normal University Changchun 130021China State Key Laboratory of Molecular Engineering of Polymers Fudan UniversityShanghai 200433China Jilin Biomedical Polymers Engineering Laboratory Changchun 130022China

Stimuli-re sponsive polypeptides have been intensively investigated fo r controlled drug release,owing to their favorable biocompatibility and biodegradability.In this work,we designed and synthesized a new kind of polypeptide bearing 1,4-dithiane pendants for reactive oxygen species(ROS)-responsive drug release.The polypeptide-based block copolymer was facilely synthesized by ring-opening polymerization(ROP)of 1,4-dithian-substituted L-glutamate N-carboxyanhydride(DTG-NCA)monomer using an amino-terminated poly(ethylene glycol)methyl ether(mPEG-NH2)as the macro molecular initiator.The resulta nt block copolyme r,mPEG-b-PDTG,could self-assemble into unifo rm micelles in aqueous medium owing to its amphiphilic structure.Then,the H2 O2-triggered oxidation behaviors of the mPEG-b-PDTG micelles were studied by dynamic light scattering(DLS),FT-IR and turbidimetric assay.It was revealed that the oxidation of Thioether into sulfoxide in the side chains would result in disassembly of the micelles.Furthermore,the ROS-responsive drug release behavior of the mPEG-b-PDTG micelles was verified by using Nile Red as a model drug.MTT assay also proved that mPEG-b-PDTG was non-toxic in B16 F10 and L929 cells.Therefore,such a new class of oxidation-responsive polypeptide might provide a promising platform for ROS-responsive drug delivery.

关键词： Polypeptides ROS-responsive Self-assembly Thioether Drug release

Redox-sensitive prodrug nanoassemblies based on linoleic acid-modified docetaxel to resist breast cancers

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Acta Pharmaceutica Sinica B 2019年第2期9卷 421-432页

作者： Meng Li Liwen Zhao Tao Zhang Yue Shu Zhonggui He Yan Ma Dan Liu Yongjun Wang Wuya College of Innovation Shenyang Pharmaceutical University School of Chinese Materia Medica Guangzhou University of Chinese Medicine Key Laboratory of Structure-Based Drug Design and Discovery Ministry of Education Shenyang Pharmaceutical University

Prodrug nanoassemblies, which can refrain from large excipients, achieve higher drug loading and control drug release, have been placed as the priority in drug delivery system. Reasoning that glutathione(GSH) and reactive oxygen species(ROS) are highly upgraded in tumor tissues which makes them attractive targets for drug delivery system, we designed and synthetized a novel prodrug which utilized mono Thioether bond as a linker to bridge linoleic acid(LA) and docetaxel(DTX). This mono Thioether-linked conjugates(DTX-S-LA) could self-assemble into nanoparticles without the aid of much excipients. The mono Thioether endowed the nanoparticles redox sensitivity resulting in specific release at the tumor tissue. Our studies demonstrated that the nanoassemblies had uniform particle size, high stability and fast release behavior. DTX-S-LA nanoassemblies outperformed DTX solution in pharmacokinetic profiles for it had longer circulation time and higher area under curve(AUC). Compared with DTX solution, the redox dual-responsive nanoassemblies had comparable cytotoxic activity. Besides, the antitumor efficacy was evaluated in mice bearing 4 T1 xenograft. It turned out this nanoassemblies couldenhance anticancer efficacy by increasing the dose because of higher tolerance. Overall, these results indicated that the redox sensitivity nanoassemblies may have a great potential to cancer therapy.

关键词： Docetaxel Nanoassemblies Mono Thioether bond Linoleic acid Pharmacokinetics Antitumor efficacy

The application of sulfur-containing peptides in drug discovery

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Chinese Chemical Letters 2018年第7期29卷 1079-1087页

作者： Jiaoyan Zhao Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular EngineeringEast China Normal University State Key Laboratory of Elemento-organic Chemistry Nankai University

In recent decades, peptides as potential drugs were more and more explored with the development of non-oral medicine. There into, sulfur-containing peptide is one of the most popular aspects in peptide drugs due to the introduction of sulfur atoms leading unique properties.The purpose of the present review is to focus on the discovery of various sulfur-containing peptides with particular emphasis on their pharmacological mechanisms. This review is organized according to the structures of the sulfurcontaining peptides.

关键词： Peptides Disulfide Thioether Thiazole Drug discovery

INTERACTION OF PLASMA—LIQUID IN AN OXYGEN GLOW DISCHARGE Ⅲ.OXIDATION DESULFURIZATION OF ETHYL—Thioether

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Chinese Chemical Letters 1993年第10期4卷 883-884页

作者： Wan Ying LIU Wei LU Zheng Lan LEI Jin Kun WANG Chengdu Institute of Organic Chemistry,Academia Sinica Chengdu 610015

A few factors affecting plasma oxidation desulfurization of ethyl- Thioether were investigated.Under the typical conditions,the conversion and degree of desulfurization of ethyl-Thioether can be achieved up to 88% and... 详细信息

关键词： OC OXIDATION DESULFURIZATION OF ETHYL Thioether INTERACTION OF PLASMA LIQUID IN AN OXYGEN GLOW DISCHARGE

Synthesis,Crystal Structure and Antifungal Activities of 3-Methyl-1-(4-methylphenyl)-4-(N-4-trifluoromethylphenyl)-aminomethyl-5-(4-methoxyphenylthio)-1H-pyrazole

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Chinese Journal of Structural Chemistry 2014年第1期33卷 37-42页

作者：徐应淑史大斌 School of Pharmaceutical Sciences Zunyi Medical College

The title compound 3-methyl-l-（4-methylphenyl）-4-（N-4-trifluoromethylphenyl） aminomethyl-5-（4-methoxyphenylthio）-lH-pyrazole has been synthesized via a four-step reaction and characterized by IR, 1H NMR, elemental analysis and X-ray crystallography. The compound crystallizes in monoclinic, space group P21/c with a = 8.7170（15）, b = 18.355（3）, c = 15.292（3） A, fl = 103.445（3）°, V= 2379.7（7） A3, Dc = 1.350 g/cm3, Z = 4, p = 0.184, F（000） = 1008, and the final R = 0.0491 and wR = 0.1339 for 4160 observed reflections （I 〉 2a（/））. The results demonstrate that there is a face-to-face π-π stacking interaction between one benzene ring （C（19）-C（24）） and another （C（I 3）-C（! 8）） at a plane-plane distance of 3.3539 A. The ring normal and vector between the ring centroids form an angle of 18.2° up to the centroid-to-centroid distance of 3.5273 A. The crystal structure is stabilized by the intermolecular hydrogen bond of N（3）-H（3A）...N（2）（symmetry code： A -x＋l, -y＋l, -z）. The preliminary biological test shows that the title compound has a moderate antifungal activity.

关键词： pyrazole crystal structure Thioether synthesis antifungal activity