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Discovery of Novel Anthranilic Diamide Derivatives Bearing sulfoximine Group as Potent Insecticide Candidates

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Chemical Research in Chinese Universities 2024年第1期40卷 96-108页

作者： ZHANG Hongyuan PENG Jinmin ZHONG Yuanhan CHEN Yue WANG Qing Haditullah HADIATULLAH XIE Weibin XIONG Lixia YUCHI Zhiguang LIU Jingbo LI Yuxin State Key Laboratory of Elemento-Organic Chemistry College of ChemistryNankai UniversityTianjin300071P.R.China Nankai University&Cangzhou Bohai New Area Institute of Green Chemical Engineering Changzhou062550P.R.China College of Horticulture and Landscape Architecture Tianjin Agricultural UniversityTianjin300392P.R.China Tianjin Key Laboratory for Modern Drug Delivery and High-efficiency Collaborative Innovation Center of Chemical Science and EngineeringSchool of Pharmaceutical Science and TechnologyTianjin UniversityTianjin300072P.R.China

The fall armyworm,Spodoptera frugiperda(***),represents the most resistant insect species and poses serious threat to grain ***(CHL),which targets the ryanodine receptors(RyRs)in insects,has demonstrated the efficacy in controlling ***,this has led to emerging resistance in several *** counter this resistance,a viable approach involves the development of novel compounds that bind against RyRs via distinct binding sites or *** this study,a series of 22 novel anthranilic diamide derivatives was designed and synthesized,and their insecticidal activities were *** of these derivatives showed moderate to good insecticidal activity against *** and Mythimna ***-lapse fluorescence measurements of endoplasmic reticulum luminal calcium revealed that most derivatives elicited cellular responses similar as CHL when assessed on HEK293 cells expressing *** ryanodine receptors(SfRyRs).The mode of action of compound 13a was studied and verified on the isolated neurons by calcium imaging ***,molecular docking analysis was employed to predict the binding mechanism of compound 13a against ***,these novel diamide derivatives hold promise as a valuable resource for guiding the future design of insecticidal compounds targeting RyRs.

关键词： Anthranilic diamide derivative sulfoximine Spodoptera frugiperda Mode of action Molecular docking

Difluoromethyl 2-Pyridyl sulfoximine:A Stereoselective Nucleophilic Reagent for Difluoro(aminosulfinyl)methylation and Difluoro(aminosulfonyl)methylation

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CCS Chemistry 2022年第11期4卷 3648-3659页

作者： Qinghe Liu Chuanfa Ni Qian Wang Depei Meng Jinbo Hu Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032

1,1-Difluorinated sulfonamides are known to have better anti-inflammatory activity and enzyme inhibitory potency than their nonfluorinated *** geminal fluorine atoms cause electronic perturbation of the nearby polar groups enhanced the biological activity of the 1,1-difluorinated ***,because methods for their stereoselective synthesis are scarce,such entities remain entirely ***,we outline an efficient method for the stereoselective introduction of the difluoro(aminosulfonyl)methyl group(CF_(2)SO_(2)NH_(2))into carbonyls,imines,and alkyl halides with a new(R)-2-pyridyl difluoromethyl sulfoximine reagent,which provides a unique solution for the synthesis of chiralα,α-difluorinated sulfonamides with a quaternary *** potency is illustrated by the synthesis of fluorinated analogues of bioactive compounds such as 2-OH-SA,an antagonist for the GABA_(B)receptor in guinea pig ileum,and the late-stage modification of complex molecules such as haloperidol,ebastine,cholesterol,and(+)-δ-tocopherol *** difluoro(aminosulfinyl)methylation to yield chiral sulfinylamides is presented,showcasing other uses of this new reagent.

关键词： difluoro(aminosulfonyl)methylation difluoro(aminosulfinyl)methylation stereoselective nucleophilic sulfoximine

通过α-甲基烷基化反应合成sulfoximine类衍生物

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合成化学 2009年第1期17卷 97-99页

作者：张宇孙健中国科学院成都生物研究所天然产物研究中心四川成都610041 中国科学院研究生院北京100039

从sulfoximine A出发,选取对甲氧基苄基(PMB)为N-保护基,通过α-甲基的烷基化反应合成了一系列新的sulfoximine类衍生物,其结构经1HNMR确证。

关键词： sulfoximine α-甲基烷基化保护基合成

Synthesis,Crystal Structure and Biological Activity of N-cyanosulfoximine Derivative Containing 1,2,3-Thiadiazole

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Chinese Journal of Structural Chemistry 2015年第9期34卷 1428-1433页

作者：毛武涛宗广宁范志金李凤云宋海斌李娟娟 Kalinina A.Tatiana Khazhieva Inna Lugovik Ksenia Morzherin Yu.Yury Belskaya P.Nataliya State Key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)Nankai University College of Chemistry and Pharmacy Engineering Nanyang Normal University The Ural Federal University Named after the First President of Russia B.N.Yeltsin

The title compound N-cyanosulfoximine derivative containing 1,2,3-thiadiazole （C6HsN4OS2, Mr = 216.28） has been synthesized using 4-（chloromethyl）-5-methyl-1,2,3-thiadiazole as the starting material, and its structure was characterized by IR, 1H NMR, HRMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to orthorhombic, space group Pna21 with a = 14.730（6）, b = 5.478（2）, c = 22.619（9） A, Z = 8, V = 1825.0（13） A3, Dc = 1.574 g/cm3,/a = 0.547 mm-1, F（000） = 896, R = 0.0767 and wR （I〉 2o（/）） = 0.2064. X-ray analysis indicates that in this crystal double enantiomers are found as the basically asymmetrical unit and interactions between S（1）...N（3）, S（3）...N（4） and S（3）...N（7） are observed. This kind of interactions extends the molecules into a one-dimensional double chain. The preliminary biological test showed that the title compound had insecticidal activity against Myzus persicae in a certain degree and also presented moderate potential bioactivity against tobacco mosaic virus （TMV）.

关键词： 1,2,3-thiadiazole sulfoximine crystal structure synthesis biological activity

Cp*Rh/Ag catalyzed C–H activation/cyclization sequences of NH-sulfoximines to fused aza-polyheterocycles under gentle conditions

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Green Synthesis and Catalysis 2023年第2期4卷 160-168页

作者： Jiapian Huang Fei Liu Feihua Du Linghui Zeng Zhiyuan Chen College of Chemistry&Chemical Engineering Jiangxi Normal UniversityNanchang 330022China Institute for Advanced Studies Taizhou UniversityTaizhou 318000China School of Medicine Zhejiang University City CollegeHangzhou 310015China

Disclosed herein is a novel Rh/Ag co-catalyzed S=NH directed C–H activation and C–H/N–H bond functionalization protocol of free NH-sulfoximines with hypervalent iodonium *** the aid of AgOTf,these C–H functionalization/cyclization sequences could be achieved at room temperature *** reaction employed EtOH as a“green”solvent and low catalyst loading was required under an oxygen/water-insensitive *** this mild protocol,a wide range of polyheterocyclic sulfoximines bearing fused saturated carbo(hetero)cycles are readily prepared,even toward a complex pharmaceutical Folliculin analog.

关键词： Rhodium catalysis C-H activation sulfoximine Polyheterocycle Cyclization

Nucleophilic Difluoro(phenylsulfonimidoyl)methylation of Unactivated Alkyl Bromides with PhSO(NTBS)CF_(2)H: Facile Entry into gem-Difluoroalkenes

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Chinese Journal of Chemistry 2014年第8期32卷 703-708页

作者： Xiao Shen Qinghe Liu Chuanfa Ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

An efficient nucleophilic difluoro(phenylsulfonimidoyl)methylation of unactivated primary alkyl bromides with PhSO(NTBS)CF_(2)H has been *** is particularly remarkable that,when 1.5 *** alkyl bromides are used,the substitution products are obtained in moderate to excellent *** prepared difluoro(phenylsulfonimidoyl)methylated alkanes can be readily transformed to gem-difluoroalkenes via base-mediatedβ-elimination reaction.

关键词： nucleophilic fluoroalkylation β-elimination difluoroalkene sulfoximine

The timing and extent of intraosseous hypoxia in the oxidative stress-induced rat osteonecrosis model

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Advances in Bioscience and Biotechnology 2013年第8期4卷 814-817页

作者： Toru Ichiseki Ayumi Kaneuji Seiji Kaneko Syusuke Ueda Yoshimichi Ueda Hideto Yonekura Kiyokazu Fukui Tadami Matsumoto Department of Biochemistry Kanazawa Medical University Uchinada Ishikawa Japan Department of Orthopaedic Surgery Kanazawa Medical University Uchinada Ishikawa Japan Department of Pathophysiological and Experimental Pathology Kanazawa Medical University Uchinada Ishikawa Japan

Using a rat oxidative stress-induced femoral head osteonecrosis model, we determined the presence/ absence and timing of the generation of hypoxia in the femoral head. DL-Buthionine-(S,R)-sulfoximine (BSO) 500 mg/kg was administered intraperitoneally to male Wistar rats. The rats were killed at 1, 3, 6, 12 hours, and 1, 3, 5 days after BSO administration, and the bilateral femora were removed. A group not administered BSO (control group) was also studied (each group n = 5). In the femoral heads of each group, the expression of hypoxia-inducible factor-1 alpha (HIF-1α) as an index of hypoxia was confirmed by the Western blot method, and quantified using analytical software. In the femoral head increased HIF-1α expression was found in all groups from 1 hour after BSO administration (p < 0.05). In particular, in all specimens of the group 3 hours after BSO administration the most intense expression of HIF-1α amounting to about 13-fold of that of control group was noted (p < 0.001). The present results suggested that in the extremely short period of 3 hours after BSO administration hypoxia severe enough to cause osteonecrosis was induced by oxidative stress in the rat femoral head.

关键词： Osteonecrosis Oxidative Stress Buthionine sulfoximine Hypoxia-Inducible Factor-1α