A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H4SiW12O40)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides...A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H4SiW12O40)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3,4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3,4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations.展开更多
A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides(1-20) was synthesized and tested for in vitro antimicrobial activity.The results of antimicrobial studies indicated that the compounds having d...A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides(1-20) was synthesized and tested for in vitro antimicrobial activity.The results of antimicrobial studies indicated that the compounds having dinitro,methoxy,hydroxy and nitro substituents on phenyl ring of the aromatic acids were most active ones.The QSAR investigation indicated the importance of the topological parameter,third order molecular connectivity index(~3x) in describing the antimicrobial activity of synthesized hydrazides.展开更多
New lanthanide(Eu3+ and Gd3+) complexes were successfully synthesized and the effect of the p-phe nyl substituent on the Eu3+luminescent properties was evaluated.In this sense,benzhydrazide,p-toluic hydrazide,4-hydrox...New lanthanide(Eu3+ and Gd3+) complexes were successfully synthesized and the effect of the p-phe nyl substituent on the Eu3+luminescent properties was evaluated.In this sense,benzhydrazide,p-toluic hydrazide,4-hydroxybenzhydrazide and 4-aminobenzoic hydrazide were used as ligands and the complexes were obtained by mixing the lanthanide salts with hydrazides in ethanol at room temperature and keeping the reaction for 2 h under mechanical stirring.Crystal of Gd-amino was obtained and its structure was elucidated by single-crystal X-ray diffraction,revealing that Gd3+centered in a distorted tricapped trigonal-prismatic molecular geometry.IR spectroscopy and the elucidated structure confirm hydrazides acting as bidentate ligands binding to Ln3+ions through the oxygen of carbonyl group and the nitrogen of terminal amine,forming a five-membered ring,CHN analyses confirm the molecular formulas [Gd(amino)4(H2 O)](NO3)3·(C2 H5 OH) and [Eu(toluic)3(H2 O)3](NO3)3.Lower T1 state energies are observed for ligands p-substituted with higher electron donating capacity groups,such as p-NH2 and pOH.In contrast,higher lifetimes and quantum efficiencies are obtained for Eu3+complexes with ligands p-H and p-CH3 substituted,which are not deactivator groups.展开更多
We regret the omission of supplementary files in the original article.The author would like to apologise for any inconvenience caused.This article has an error in Scheme 1.The new Scheme 1 to this article is shown below.
The presence of fluorine in biologically active compounds can impart a profound influence on their biological active. This influence has lead to the development of several potent agricultural and therapeutic agents[1]...The presence of fluorine in biologically active compounds can impart a profound influence on their biological active. This influence has lead to the development of several potent agricultural and therapeutic agents[1]. During the study on the reactions of 4 - ethoxyl - 1, 1, 1 -trifluoromathyl-3-butenone 1, we found which is a very useful building-block in synthesis of fluoro-containing heterocyclic compounds[2]. Compound 1 can react with perfluorophenyl hydrazine and afford 1- perfluorophenyl-5-trifluoromethyl- 5 -hydroxy-4, 5 -2H- pyrazole 2 in excellent yield. It’s structure is further supported by X-ray diffraction.展开更多
The C-terminal conjugate of ubiquitin with 7-amino-4-methylcoumarin (Ub-AMC) is an important probe for fluorescencebased analysis of deubiquitinating enzyme (DUB) activity. It is important to develop more efficien...The C-terminal conjugate of ubiquitin with 7-amino-4-methylcoumarin (Ub-AMC) is an important probe for fluorescencebased analysis of deubiquitinating enzyme (DUB) activity. It is important to develop more efficient methods for the preparation of Ub-AMC because the currently available technology is still expensive for scaled-up production. In the present work we report an efficient strategy for total chemical synthesis of Ub-AMC through ligation of peptide hydrazides. Three peptide segments are assembled via N-to-C sequential ligation and the resulting product is converted to Ub-AMC via TCEP-mediated desulfurization. The synthetic Ub-AMC is shown to have expected biological functions throug展开更多
A new Ce3+modified Dawson-like polyoxometalate cluster(C2H8N)12Na2[H10{Ce(H2O)5}2(Te2W37O132)]·39H2O was synthesized using pH and temperature-controlled one-pot strategy....A new Ce3+modified Dawson-like polyoxometalate cluster(C2H8N)12Na2[H10{Ce(H2O)5}2(Te2W37O132)]·39H2O was synthesized using pH and temperature-controlled one-pot strategy.The compound was characterized by single-crystal X-ray structure analysis,IR spectroscopy,thermogravimetric(TG)analysis,X-ray photoelectron spectroscopy(XPS),and electrospray ionization mass spectrometry(ESI-MS).Singlecrystal X-ray structure analysis revealed that there was a new{Te2W37O132}structure and two Ce3+in this compound.Moreover,it is notable that this compound presents excellent Lewis acid-and Lewis base activities in the condensation cyclization of 1,3-diketones with hydrazines/hydrazides or diamines.All the desired products were obtained in moderate to good yields(up to 99%)and with a high turnover number(up to 4347).展开更多
Main observation and conclusion Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations.However,carbon-carbon cleavage reaction tri...Main observation and conclusion Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations.However,carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen,is scarce and underdeveloped.Herein,we report alkoxy radical,which was generated from alkyl radical and dioxygen,mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes,providing facile access to a variety of valuableβ-keto sulfones.Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselectiveβ-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C-C bond cleavage.Notably,the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.展开更多
A novel sulfur-promoted cyclization of hydrazides and isonitriles to produce 1,3,4-oxadiazole has been devel- oped. The method is operationally simple and compatible with a wide scope of substrates and various 2-amino...A novel sulfur-promoted cyclization of hydrazides and isonitriles to produce 1,3,4-oxadiazole has been devel- oped. The method is operationally simple and compatible with a wide scope of substrates and various 2-amino- 1,3,4-oxadiazoles are efficiently obtained in good yields.展开更多
An efficient palladium-catalyzed sulfonylative coupling for the synthesis of benzyl(allyl)sulfones from sulfonyl hydrazides and carbonates was developed.The novel methodology employs easily accessible chemical feedsto...An efficient palladium-catalyzed sulfonylative coupling for the synthesis of benzyl(allyl)sulfones from sulfonyl hydrazides and carbonates was developed.The novel methodology employs easily accessible chemical feedstocks including stable and readily available arylsulfonyl hydrazides and benzyl(allyl)carbonates.A variety of benzyl(allyl)sulfones could be obtained in good to excellent yields in the presence of Pd(dppf)Cl2 without additional base under mild conditions.展开更多
A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to goo...A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper.展开更多
An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed o...An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.展开更多
Main observation and conclusion Selenoesters are useful substitutes for traditional thioesters in protein ligation chemistry due to their high reactivity in the trans-thio/selenoesterification reaction.However,existin...Main observation and conclusion Selenoesters are useful substitutes for traditional thioesters in protein ligation chemistry due to their high reactivity in the trans-thio/selenoesterification reaction.However,existing synthetic routes to access peptide selenoester require a selenoesterification reaction between a selenide and a protected peptide with a free carboxylate at the C-terminus.展开更多
Polyethylene glycol (PEG) supported (diacetoxy)iodobenzene as soluble polymer reagent can smoothly oxidize acid hydrazides into corresponding dimmers in good yields under very mild conditions.
2,5-Di-substituted 1,3,4-oxadiazoles 3a-n have been synthesized as a one pot procedure from the reaction of acid hydrazide 1, acyl halides 2 and phosphorus pentoxide in acetonitrile at room temperature. High yield, sh...2,5-Di-substituted 1,3,4-oxadiazoles 3a-n have been synthesized as a one pot procedure from the reaction of acid hydrazide 1, acyl halides 2 and phosphorus pentoxide in acetonitrile at room temperature. High yield, short reaction time (10-15 min), mild condition, and easy work-up are advantages of this methodology.展开更多
TNFR1-associated death domain protein(TRADD)with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification(PTM)glycoprotein that blocks the formation of death-inducing signaling comple...TNFR1-associated death domain protein(TRADD)with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification(PTM)glycoprotein that blocks the formation of death-inducing signaling complex(DISC),orchestrating host nuclear factorκB(NF-κB)signaling in entero-pathogenic Escherichia coli(EPEC)-infected cells.This particular glycosylated modification plays an extremely vital role for the effective colonization and pathogenesis of pathogens in the gut.Herein we describe the total synthesis of TRADD death domain(residues 195-312)with arginine235 NGlcNAcylation(Arg-GIcNAc TRADD(195-312)).Two longish peptidyl fragments of the wild-type primary sequence were obtained by robust,microwave-assisted,highly efficient,solid-phase peptide synthesis(SPPS),the N-GlcNAcylated sector was built by total synthesis and attached specifically to resinbound peptide with an unprotected ornithine residue via silver-promoted on-resin guanidinylation,ArgGlcNAc TRADD(195-312)was constructed by hydrazide-based native chemical ligation(NCL).The facile synthetic strategy is expected to be generally applicable for the rapid synthesis of other proteins with Arg-GIcNAc modification and to pave the way for the related chemically biological study.展开更多
Nicotinic acetylcholine receptors(nAChRs) play important roles in intercellular communications of nerve cells. α-Bungarotoxins(αBtx) is a moderator for the nAChRs. Chemical synthesis provides a promising way to acce...Nicotinic acetylcholine receptors(nAChRs) play important roles in intercellular communications of nerve cells. α-Bungarotoxins(αBtx) is a moderator for the nAChRs. Chemical synthesis provides a promising way to access aBtx and their analogues. Here, we reported a new method for a-bungarotoxin by combining Fmoc-SPPS and peptide hydrazide based ligation strategy. The two-segment ligation method may enable efficient synthesis of aBtx analogues. These synthetic toxin peptides are useful tools for development of imaging or therapeutic reagents.展开更多
N-(1-Phenyl-3-methyl-4-benzal-pyrazolone-5)-furoic hydrazide (PMBP-FUH, C22H18N4O3, CCDC No: 188946) has been synthesized and characterized by IR spectrum, 1H NMR and single-crystal X-ray diffraction. The crystal is o...N-(1-Phenyl-3-methyl-4-benzal-pyrazolone-5)-furoic hydrazide (PMBP-FUH, C22H18N4O3, CCDC No: 188946) has been synthesized and characterized by IR spectrum, 1H NMR and single-crystal X-ray diffraction. The crystal is of orthorhombic, space group Pbca with a = 11.870(2), b = 15.951(3), c = 19.674(3) ? V = 3725.0(11) ?, Mr = 386.40, Z = 8, Dc = 1.378 g/cm3, F(000) = 1616, R = 0.0455 and wR = 0.0809. The inter- or intramolecular hydrogen bonds result in the formation of three-dimensional network structure.展开更多
A series of novel 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), ...A series of novel 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc). The in vitro antifungal bioassays indicated that most of title compounds displayed good selectivity and specificity aganist Rs relative to Fg, Bc and Cc. Strikingly, the title compound N'-(4-chlorophenyl)-2-(5-phenyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acethydrazide (5b) obviously inhibited the Rs growth in vitro with the EC50 value of 0.24μg/mL, which is approximately 2-folds more effective than the commercialized fungicide carbendazim (0.55 μg/mL). The in vivo anti-Rs effects of title compound 5b were further evaluated on rice leaves with control efficacies of 98.58% at 200 μg/mL and 61.27% at 100 μg/mL. The above researches provide a significant reference for the further structural optimization of 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety as potential fungicides.展开更多
A series of novel neonicotinoid analogues were designed and synthesized by introducing a hydrazide group into clothianidin. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI). Preliminary bioassay showed ...A series of novel neonicotinoid analogues were designed and synthesized by introducing a hydrazide group into clothianidin. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI). Preliminary bioassay showed that some compounds, Sb and Sg, exhibited good activity against soybean aphids (Aphis glycines) at 100 mg L ^-1. In addition, molecular docking with receptor was carried out to explain their different activity from clothianidin.展开更多
基金financially supported by the National Natural Science Foundation of China (Nos. 22001034 and 21804019)the Open Fund of the Jiangxi Province Key Laboratory of Synthetic Chemistry (No. JXSC202008)the Research Found of East China University of Technology (Nos. DHBK2019264, DHBK2019265 and DHBK2019267)。
摘要A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H4SiW12O40)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3,4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3,4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations.
摘要A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides(1-20) was synthesized and tested for in vitro antimicrobial activity.The results of antimicrobial studies indicated that the compounds having dinitro,methoxy,hydroxy and nitro substituents on phenyl ring of the aromatic acids were most active ones.The QSAR investigation indicated the importance of the topological parameter,third order molecular connectivity index(~3x) in describing the antimicrobial activity of synthesized hydrazides.
基金the FAPESP(Fundacao de Amparo a Pesquisa de Sao Paulo)(2017/11764-2)。
摘要New lanthanide(Eu3+ and Gd3+) complexes were successfully synthesized and the effect of the p-phe nyl substituent on the Eu3+luminescent properties was evaluated.In this sense,benzhydrazide,p-toluic hydrazide,4-hydroxybenzhydrazide and 4-aminobenzoic hydrazide were used as ligands and the complexes were obtained by mixing the lanthanide salts with hydrazides in ethanol at room temperature and keeping the reaction for 2 h under mechanical stirring.Crystal of Gd-amino was obtained and its structure was elucidated by single-crystal X-ray diffraction,revealing that Gd3+centered in a distorted tricapped trigonal-prismatic molecular geometry.IR spectroscopy and the elucidated structure confirm hydrazides acting as bidentate ligands binding to Ln3+ions through the oxygen of carbonyl group and the nitrogen of terminal amine,forming a five-membered ring,CHN analyses confirm the molecular formulas [Gd(amino)4(H2 O)](NO3)3·(C2 H5 OH) and [Eu(toluic)3(H2 O)3](NO3)3.Lower T1 state energies are observed for ligands p-substituted with higher electron donating capacity groups,such as p-NH2 and pOH.In contrast,higher lifetimes and quantum efficiencies are obtained for Eu3+complexes with ligands p-H and p-CH3 substituted,which are not deactivator groups.
摘要We regret the omission of supplementary files in the original article.The author would like to apologise for any inconvenience caused.This article has an error in Scheme 1.The new Scheme 1 to this article is shown below.
基金The authors thank the National Natural Science Foundation ofChina (NNSFC) !(No. 29872051 and No 29672041 ) for financial support
摘要The presence of fluorine in biologically active compounds can impart a profound influence on their biological active. This influence has lead to the development of several potent agricultural and therapeutic agents[1]. During the study on the reactions of 4 - ethoxyl - 1, 1, 1 -trifluoromathyl-3-butenone 1, we found which is a very useful building-block in synthesis of fluoro-containing heterocyclic compounds[2]. Compound 1 can react with perfluorophenyl hydrazine and afford 1- perfluorophenyl-5-trifluoromethyl- 5 -hydroxy-4, 5 -2H- pyrazole 2 in excellent yield. It’s structure is further supported by X-ray diffraction.
基金National Basic Research Program of China (973 program, 2013CB932800)the National Natural Science Foundation of China (NSFC, 31100524 to M.Z., 31170817 for C.T., and 20972148 to L.L.)
摘要The C-terminal conjugate of ubiquitin with 7-amino-4-methylcoumarin (Ub-AMC) is an important probe for fluorescencebased analysis of deubiquitinating enzyme (DUB) activity. It is important to develop more efficient methods for the preparation of Ub-AMC because the currently available technology is still expensive for scaled-up production. In the present work we report an efficient strategy for total chemical synthesis of Ub-AMC through ligation of peptide hydrazides. Three peptide segments are assembled via N-to-C sequential ligation and the resulting product is converted to Ub-AMC via TCEP-mediated desulfurization. The synthetic Ub-AMC is shown to have expected biological functions throug
基金Natural Science Foundation of China(21501010,21231002,21671019)the 111 Project(B07012)for financial support.
摘要A new Ce3+modified Dawson-like polyoxometalate cluster(C2H8N)12Na2[H10{Ce(H2O)5}2(Te2W37O132)]·39H2O was synthesized using pH and temperature-controlled one-pot strategy.The compound was characterized by single-crystal X-ray structure analysis,IR spectroscopy,thermogravimetric(TG)analysis,X-ray photoelectron spectroscopy(XPS),and electrospray ionization mass spectrometry(ESI-MS).Singlecrystal X-ray structure analysis revealed that there was a new{Te2W37O132}structure and two Ce3+in this compound.Moreover,it is notable that this compound presents excellent Lewis acid-and Lewis base activities in the condensation cyclization of 1,3-diketones with hydrazines/hydrazides or diamines.All the desired products were obtained in moderate to good yields(up to 99%)and with a high turnover number(up to 4347).
基金Fund of Luzhou Government and Southwest Medical University(Nos.2019LZXNYDJ28,2018LZXNYD-ZK33,2018LZXNYD-ZK39)the Open Project of Central Nervous System Drug Key Laboratory of Sichuan Province(No.200023-01SZ)the research fund of Southwest Medical University(Nos.2017-ZRZD-020 and 2017-ZRQN-031).
摘要Main observation and conclusion Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations.However,carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen,is scarce and underdeveloped.Herein,we report alkoxy radical,which was generated from alkyl radical and dioxygen,mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes,providing facile access to a variety of valuableβ-keto sulfones.Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselectiveβ-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C-C bond cleavage.Notably,the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.
摘要A novel sulfur-promoted cyclization of hydrazides and isonitriles to produce 1,3,4-oxadiazole has been devel- oped. The method is operationally simple and compatible with a wide scope of substrates and various 2-amino- 1,3,4-oxadiazoles are efficiently obtained in good yields.
基金We gratefully acknowledge the National Natural Science Foundation of China(Nos.21801040,22008028,22102022)the Natural Science Foundation of Jiangxi Province(Nos.20192BAB213006,20181BBH80007)+1 种基金the Opening Project of Jiangxi Province Key Laboratory of Polymer Micro/Nano Manufacturing and Devices(Nos.PMND202001,PMND202003)East China University of Technology Research Foundation for Advanced Talents(No.DHBK2017168)provides financial support.
摘要An efficient palladium-catalyzed sulfonylative coupling for the synthesis of benzyl(allyl)sulfones from sulfonyl hydrazides and carbonates was developed.The novel methodology employs easily accessible chemical feedstocks including stable and readily available arylsulfonyl hydrazides and benzyl(allyl)carbonates.A variety of benzyl(allyl)sulfones could be obtained in good to excellent yields in the presence of Pd(dppf)Cl2 without additional base under mild conditions.
摘要A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper.
摘要An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.
基金Financial support for this work was gratefully received from the National Natural Science Foundation of China(Nos.22077080,21907064 and 91753102)the Interdisciplinary Program of Shanghai Jiao Tong University(No.YG2020YQ14).
摘要Main observation and conclusion Selenoesters are useful substitutes for traditional thioesters in protein ligation chemistry due to their high reactivity in the trans-thio/selenoesterification reaction.However,existing synthetic routes to access peptide selenoester require a selenoesterification reaction between a selenide and a protected peptide with a free carboxylate at the C-terminus.
基金We are grateful for the financial support from the Postdoctoral Foundation of China.
摘要Polyethylene glycol (PEG) supported (diacetoxy)iodobenzene as soluble polymer reagent can smoothly oxidize acid hydrazides into corresponding dimmers in good yields under very mild conditions.
摘要2,5-Di-substituted 1,3,4-oxadiazoles 3a-n have been synthesized as a one pot procedure from the reaction of acid hydrazide 1, acyl halides 2 and phosphorus pentoxide in acetonitrile at room temperature. High yield, short reaction time (10-15 min), mild condition, and easy work-up are advantages of this methodology.
基金the National Natural Science Foundation of China (Nos.91849129,21807112)PLA Youth Medical Science and Technology Youth Development Program (No.16QNP086)Foundation of Second Military Medical University (No.2016JS11)
摘要TNFR1-associated death domain protein(TRADD)with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification(PTM)glycoprotein that blocks the formation of death-inducing signaling complex(DISC),orchestrating host nuclear factorκB(NF-κB)signaling in entero-pathogenic Escherichia coli(EPEC)-infected cells.This particular glycosylated modification plays an extremely vital role for the effective colonization and pathogenesis of pathogens in the gut.Herein we describe the total synthesis of TRADD death domain(residues 195-312)with arginine235 NGlcNAcylation(Arg-GIcNAc TRADD(195-312)).Two longish peptidyl fragments of the wild-type primary sequence were obtained by robust,microwave-assisted,highly efficient,solid-phase peptide synthesis(SPPS),the N-GlcNAcylated sector was built by total synthesis and attached specifically to resinbound peptide with an unprotected ornithine residue via silver-promoted on-resin guanidinylation,ArgGlcNAc TRADD(195-312)was constructed by hydrazide-based native chemical ligation(NCL).The facile synthetic strategy is expected to be generally applicable for the rapid synthesis of other proteins with Arg-GIcNAc modification and to pave the way for the related chemically biological study.
基金supported by the Science and Technological Fund of Anhui Province for Outstanding Youth(No. 1808085J04)the Innovative Program Development Foundation Hefei Center Physical Science Technology(No. 2017FXCX002)
摘要Nicotinic acetylcholine receptors(nAChRs) play important roles in intercellular communications of nerve cells. α-Bungarotoxins(αBtx) is a moderator for the nAChRs. Chemical synthesis provides a promising way to access aBtx and their analogues. Here, we reported a new method for a-bungarotoxin by combining Fmoc-SPPS and peptide hydrazide based ligation strategy. The two-segment ligation method may enable efficient synthesis of aBtx analogues. These synthetic toxin peptides are useful tools for development of imaging or therapeutic reagents.
基金the National Natural Science Foundation of China (No. 20262005)
摘要N-(1-Phenyl-3-methyl-4-benzal-pyrazolone-5)-furoic hydrazide (PMBP-FUH, C22H18N4O3, CCDC No: 188946) has been synthesized and characterized by IR spectrum, 1H NMR and single-crystal X-ray diffraction. The crystal is of orthorhombic, space group Pbca with a = 11.870(2), b = 15.951(3), c = 19.674(3) ? V = 3725.0(11) ?, Mr = 386.40, Z = 8, Dc = 1.378 g/cm3, F(000) = 1616, R = 0.0455 and wR = 0.0809. The inter- or intramolecular hydrogen bonds result in the formation of three-dimensional network structure.
基金the grants from the National Natural Science Foundation of China (No. 31772209)the Fundamental Research Funds for the Central Universities of China (No. KYTZ201604)
摘要A series of novel 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc). The in vitro antifungal bioassays indicated that most of title compounds displayed good selectivity and specificity aganist Rs relative to Fg, Bc and Cc. Strikingly, the title compound N'-(4-chlorophenyl)-2-(5-phenyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acethydrazide (5b) obviously inhibited the Rs growth in vitro with the EC50 value of 0.24μg/mL, which is approximately 2-folds more effective than the commercialized fungicide carbendazim (0.55 μg/mL). The in vivo anti-Rs effects of title compound 5b were further evaluated on rice leaves with control efficacies of 98.58% at 200 μg/mL and 61.27% at 100 μg/mL. The above researches provide a significant reference for the further structural optimization of 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety as potential fungicides.
基金financially supported by the National Basic Research Program of China(No.2010CB126104)
摘要A series of novel neonicotinoid analogues were designed and synthesized by introducing a hydrazide group into clothianidin. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI). Preliminary bioassay showed that some compounds, Sb and Sg, exhibited good activity against soybean aphids (Aphis glycines) at 100 mg L ^-1. In addition, molecular docking with receptor was carried out to explain their different activity from clothianidin.