In this short review, excerpts from the literature of azo-bridged triazoles(mainly 1,2,4-triazoles), some of their derivatives(chloromethyl,dinitro and trinitro pyrazole substituted ones, etc.) and some of their salts...In this short review, excerpts from the literature of azo-bridged triazoles(mainly 1,2,4-triazoles), some of their derivatives(chloromethyl,dinitro and trinitro pyrazole substituted ones, etc.) and some of their salts, have been presented focusing on the most recent investigations. These classes of compounds, known as high nitrogen compounds, are generally high energy density materials. Therefore, if available some of their ballistic properties were included.展开更多
In this paper, the fully optimized molecular geometries and electronic structures of six 1,2,3- and 1,2,4-triazoles were calculated using density functional theory B3LYP/6-311G^＊＊ method. The salvation energies were...In this paper, the fully optimized molecular geometries and electronic structures of six 1,2,3- and 1,2,4-triazoles were calculated using density functional theory B3LYP/6-311G^＊＊ method. The salvation energies were obtained by SCRF in THF. The results show that the total energies of F are the lowest both in gas and liquid phases, and the order of thermodynamic stabilities of the title compounds is F〉D〉C〉B〉E〉A. Their frontier orbital energy gaps and electron delocalization also support that F is the most stable. All the computed conclusions are in good agreement with the experiments. Vibrational frequencies of the title compounds were computed. The thermodynamic properties and their temperature curves of six compounds were obtained by using the statistical thermodynamic method with the temperature ranging from 200 to 1000 K.展开更多
Poly（4-vinyl pyridine） supported nanoparticle of copper（Ⅰ） iodide is reported as a green and recyclable catalyst for the regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides,sodium...Poly（4-vinyl pyridine） supported nanoparticle of copper（Ⅰ） iodide is reported as a green and recyclable catalyst for the regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides,sodium azide and terminal alkynes in water. This catalyst can be recovered by simple filtration and recycled up to 8 consecutive runs without any loss of its efficiency.展开更多
Heterocyclic ketene aminals 1 react with aryl azides 2 to give the titled compounds 3,and in some cases also with the formation of fused heterocycles 4.
A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide.The reaction is mild a...A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide.The reaction is mild and simple,does not require a transition-metal catalyst,and gives products in good to excellent yields.展开更多
An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of m...An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of monosubstituted and unsubstituted triazole substrates with various olefins, including vinyl esters, are explored.展开更多
Difluorocarbene has emerged as a valuable intermediate to synthesize fluorides.However,difluorocarbene-derived synthesis of^(19)F/^(18)F-trifluoromethyl triazoles has not been explored.Herein,we reported the Cu(I)-pro...Difluorocarbene has emerged as a valuable intermediate to synthesize fluorides.However,difluorocarbene-derived synthesis of^(19)F/^(18)F-trifluoromethyl triazoles has not been explored.Herein,we reported the Cu(I)-promoted difluorocarbene-derived^(19)F/^(18)F-trifluoromethylation of iodotriazoles using KF/K^(18)F as the fluorine source.This approach rapidly generated a wide range of 5-trifluoromethyl-1,2,3-triazoles in good yields showing high functional group compatibility.The reaction was effective for late-stage functionalization of bioactive molecules and^(18)F-trifluoromethylation of iodotriazoles.This work provides a practical synthetic methodology for the development of triazole drugs and^(18)F-radiotracers for positron emission tomography.展开更多
Aryl azides and a-keto phosphorus ylides were reacted within 4 similar to 10 minutes with silica gel support, under microwave irridiation to afford corresponding 1-aryl-1, 2, 3-triazoles in moderate to good yields.
A copper-catalyzed tandem click/amidation reaction involving various alkynes,azides,and dioxazolones has been developed for the synthesis of fully substituted 5-amide-1,2,3-triazoles.The key step in this reaction is t...A copper-catalyzed tandem click/amidation reaction involving various alkynes,azides,and dioxazolones has been developed for the synthesis of fully substituted 5-amide-1,2,3-triazoles.The key step in this reaction is the interception of the in situ-formed cuprate-triazole intermediate with N-acyl nitrenes,which are generated from dioxazolones.The choice of precursor for the N-acyl nitrenes plays a crucial role in the success of the reaction.This method is characterized by a broad substrate scope,mild reaction conditions,and complete regioselectivity.展开更多
An efficient rhodium(Ⅱ)-catalyzed[4+3]cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed.Azepino[5,4,3-ccflindoles,which are widely distributed in ergot alkaloids with various biological act...An efficient rhodium(Ⅱ)-catalyzed[4+3]cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed.Azepino[5,4,3-ccflindoles,which are widely distributed in ergot alkaloids with various biological activities,could be obtained in good to excellent yields.In addition,the total synthesis of(±)-aurantioclavine was completed in four steps from the known compound 1a adopting this[4+3]cyclization as a key step.展开更多
Available online A mild and efficient photocatalytic-induced radical method has been developed for[4+1]cycloaddition reaction of 1,4-disubstituted 1,2,3-triazoles with N-tosylhydrazides and primary amines.The reaction...Available online A mild and efficient photocatalytic-induced radical method has been developed for[4+1]cycloaddition reaction of 1,4-disubstituted 1,2,3-triazoles with N-tosylhydrazides and primary amines.The reaction is catalyzed by 20 mol%of I2 under metal,azide and oxidant-free conditions.The method is based upon the photocatalytic generation of allyl-type radicals,followed by the iodine-catalyzed production of azoalkenes,which react rapidly with various anilines.展开更多
A Cul-catalyzed three-component coupling of trifluoromethyl ketone N-tosylhydrazones, alkynes and azides has been developed. The reaction represents a straightforward method to access difluoromethylene substituted 1,2...A Cul-catalyzed three-component coupling of trifluoromethyl ketone N-tosylhydrazones, alkynes and azides has been developed. The reaction represents a straightforward method to access difluoromethylene substituted 1,2,3-triazoles. Mechanistically, it has been proposed that the reaction follows a pathway involving the formation of Cu（1） triazolide intermediate, Cu（I） carbene formation, migratory insertion, and β-fluoride elimination. The trans- formation is featured by mild conditions, wide substrate scope and high efficiency.展开更多
A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new...A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution. 2-Chlorobenzyl triazolium 8g and compound 9b with octyl group exhibited the best antibacterial activities among all the tested compounds, especially against S. aureus with inhibitory concentration of 2 μg/mL which was equipotent potency to Norfloxacin(MIC=2 μg/mL) and more active than Chloromycin(MIC=7 μg/mL). Triazoliums 8g and 8f bearing 3-fluorobenzyl moiety displayed the best antifungal activities(MIC=2-19 μg/mL) against all the tested fungal strains without being toxic to PC12 cell line within concentration of 128 μg/m L. Further investigations by fluorescence and UV-Vis spectroscopic methods revealed that the compound 8g could effectively intercalate into calf thymus DNA to form the 8g-DNA complex which could block DNA replication, exerting powerful antimicrobial activities.展开更多
Azido-3,5-dichloropyridine and 2-azido-5-chloro-3-fluoropyridine were given by reaction of sodium azide with 2,3,5-trichloropyridine, 3,5-dichloro-2-fluoropyridine or 5-chloro-2,3-difluoropyridine in ionic liquids. 1,...Azido-3,5-dichloropyridine and 2-azido-5-chloro-3-fluoropyridine were given by reaction of sodium azide with 2,3,5-trichloropyridine, 3,5-dichloro-2-fluoropyridine or 5-chloro-2,3-difluoropyridine in ionic liquids. 1,3-Dipolar cycloaddition of 2-azido-3,5-dichloropyridine or 2-azido-5-chloro-3-fluoropyridine to alkynes in ionic liquids afforded the corresponding 1,4,5-trisubstituted [1,2,3]-triazoles in good yields and regioselectivities.展开更多
We here report a direct ring-opening/semipinacol rearrangement reaction of 4-(1-hydroxycyclobutyl)-1,2,3-triazole,in which N-acyl substituted 1,2,3-triazole was generated in situ and would trigger thermo-dynamically c...We here report a direct ring-opening/semipinacol rearrangement reaction of 4-(1-hydroxycyclobutyl)-1,2,3-triazole,in which N-acyl substituted 1,2,3-triazole was generated in situ and would trigger thermo-dynamically controlled electrocyclization ring-opening to afford a rearrangement precursor(α-diazo-ol).This strategy avoided the usage of metal catalysts and the reservation of sulfonyl groups on the N^(1)-posi-tion of 1,2,3-triazole.The final cycloenaminone product is highly reactive and could be commonly used as a dinucleophilic acceptor to synthesize structurally diverse fused bicyclic products.展开更多
Currently,triazole sulfonamide fungicide could be used to effectively control cucumber downy mildew(CDM),caused by Pseudoperonospora cubensis.In this study,a series of triazole sulfonamide derivatives containing diphe...Currently,triazole sulfonamide fungicide could be used to effectively control cucumber downy mildew(CDM),caused by Pseudoperonospora cubensis.In this study,a series of triazole sulfonamide derivatives containing diphenyl ether(DE)fragment were designed and synthesized.All target compounds were evaluated for their fungicidal activity against four oomycete diseases.Compound 10b showed the best activity against CDM with 40%control efficacy at 0.78 mg/L,which was the same as amisulbrom.Meanwhile,compounds 10d and 10h showed good inhibitory activity against Peronophythora litchii and compounds 10e,10f,10l and 10q showed good inhibitory activity against Phytophthora infestans.The results of computational chemistry showed that compound 10b had the same binding mode as amisulbrom and formed hydrogen bonds with the residues Gln9,His189 and Ash217.Compound 10b could be further investigated as a potential fungicide candidate.This study also provides a useful optimization strategy for the design of novel fungicides against CDM.展开更多
Seven podophyllotoxin analogues were synthesized by condensation of 4′ demethyl epipodophyllotoxin 10 with 5 alkyl 4 amino 3 mercapto 1,2,4 triazoles 9(a g) in the presence of TFA(CF 3COOH). Their antitumo...Seven podophyllotoxin analogues were synthesized by condensation of 4′ demethyl epipodophyllotoxin 10 with 5 alkyl 4 amino 3 mercapto 1,2,4 triazoles 9(a g) in the presence of TFA(CF 3COOH). Their antitumor activities were screened in vitro against HL 60 and K 562 cells.展开更多
Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperatu...Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu（OAc）2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a（C10H9N5O4） crystallizes in the triclinic system, space group P1 with a = 5.0894（9）, b = 8.9834（13）, c = 13.089（2） ？, α= 83.041（7）, β= 80.256（7）, γ=87.296（8）°, V = 585.24（16）？3, Z = 2, Mr = 263.22, crystal size（mm） = 0.37 × 0.20 ×0.18,（I 〉 2σ（I）） = 8557, 2493, 1229, Rint = 0.057. Compound 1b（C12H13N5O4） crystallizes in the monoclinic system, space group P21/c with a = 6.8854（5）, b = 21.783（2）, c = 9.3986（8） ？,β = 93.239（4）°, V = 1407.4（2）？3, Z = 4, Mr = 291.27, crystal size（mm） = 0.38 × 0.22 × 0.20,（I 〉 2σ（I）） = 11842, 3172, 1866, Rint = 0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains.展开更多
Ten new antifungal triazoles,3-sulfonanido-2-aryl-1-triazoly1-2-propanol derivatives were designed and synthesized as potential inhibitors of the fungal cytochrome P-45014a-demethylase.Results ofantifungal tests in vi...Ten new antifungal triazoles,3-sulfonanido-2-aryl-1-triazoly1-2-propanol derivatives were designed and synthesized as potential inhibitors of the fungal cytochrome P-45014a-demethylase.Results ofantifungal tests in vitro showed that compounds Ib,Ie and Ig had high activity,especially against Candida albicans.Candida parapsilosis and Fonsecaea pedrosor,but less active in comparison with ketoconazole.Compared withfluconazole,compound 1b was thirty-two times more active against Candida parapsilosis and four times more activeagainst Fonsecaea pedrosor;compound 1e was sixteen times more active against Candida parapsilosis and eighttimes more active against Fonsecaea pedrosor,compound lg was four times and eight times more active againstCandida parapsilosis and Fonsecaea pedrosor respectively.展开更多
Eleven 1-(1H-1,2,4-triazole)-2-(2,4-diflurophenyl)-3-(N-methyl-N-substituted benzylamino)-2-propanols were designed and synthesized, on the basis of the crystal structure of P450 cytochrome 14α-sterol demethylase(CYP...Eleven 1-(1H-1,2,4-triazole)-2-(2,4-diflurophenyl)-3-(N-methyl-N-substituted benzylamino)-2-propanols were designed and synthesized, on the basis of the crystal structure of P450 cytochrome 14α-sterol demethylase(CYP51) and the docking results of inhibitors to the active site of the enzyme. All title compounds were first by reported. Results of preliminary biological tests showed that most of title compounds exhibited activity against the seven common pathogenic fungi. Compound 11 showed best antifungal activity with broad antifungal spectrum and proved to be more active against Cryptococcus neoformans, Candida albicans, Microsporum lanosum and Trichophyton rubrum than ketoconazole. Compounds 3, 10 and 4 also had high activities.展开更多
文摘In this short review, excerpts from the literature of azo-bridged triazoles(mainly 1,2,4-triazoles), some of their derivatives(chloromethyl,dinitro and trinitro pyrazole substituted ones, etc.) and some of their salts, have been presented focusing on the most recent investigations. These classes of compounds, known as high nitrogen compounds, are generally high energy density materials. Therefore, if available some of their ballistic properties were included.
基金This work was supported by the Key National Natural Science Foundation of China (No. 10576030)
文摘In this paper, the fully optimized molecular geometries and electronic structures of six 1,2,3- and 1,2,4-triazoles were calculated using density functional theory B3LYP/6-311G^＊＊ method. The salvation energies were obtained by SCRF in THF. The results show that the total energies of F are the lowest both in gas and liquid phases, and the order of thermodynamic stabilities of the title compounds is F〉D〉C〉B〉E〉A. Their frontier orbital energy gaps and electron delocalization also support that F is the most stable. All the computed conclusions are in good agreement with the experiments. Vibrational frequencies of the title compounds were computed. The thermodynamic properties and their temperature curves of six compounds were obtained by using the statistical thermodynamic method with the temperature ranging from 200 to 1000 K.
文摘Poly（4-vinyl pyridine） supported nanoparticle of copper（Ⅰ） iodide is reported as a green and recyclable catalyst for the regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides,sodium azide and terminal alkynes in water. This catalyst can be recovered by simple filtration and recycled up to 8 consecutive runs without any loss of its efficiency.
文摘Heterocyclic ketene aminals 1 react with aryl azides 2 to give the titled compounds 3,and in some cases also with the formation of fused heterocycles 4.
基金supported by the Natural Science Foundation of China(No.21272174)the Key Projects of Shanghai in Biomedicine(No.08431902700)the Scientific Research Foundation of the State Education Ministry for Returned Overseas Chinese Scholars
文摘A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide.The reaction is mild and simple,does not require a transition-metal catalyst,and gives products in good to excellent yields.
基金supported by the National Natural Science Foundation of China (21272268 and 21472237)~~
文摘An efficient new method has been developed to synthesize N2‐alkyl 1,2,3‐triazole products by tol‐uenesulfonic acid （TsOH） catalyzed addition of N1‐Ts substituted 1,2,3‐triazoles to olefins. The reac‐tions of monosubstituted and unsubstituted triazole substrates with various olefins, including vinyl esters, are explored.
基金financially supported by the National Natural Science Foundation of China(Nos.21977075,22271200,21801178,21907070,81971653)1.3.5 Project for Disciplines of Excellence,West China Hospital,Sichuan University,Central Plains Science and Technology Innovation Leader Project(No.214200510008 to L.Li)Scientific and Technological Innovation Team of Colleges and Universities in Henan Province(No.21IRTSTHN001)。
文摘Difluorocarbene has emerged as a valuable intermediate to synthesize fluorides.However,difluorocarbene-derived synthesis of^(19)F/^(18)F-trifluoromethyl triazoles has not been explored.Herein,we reported the Cu(I)-promoted difluorocarbene-derived^(19)F/^(18)F-trifluoromethylation of iodotriazoles using KF/K^(18)F as the fluorine source.This approach rapidly generated a wide range of 5-trifluoromethyl-1,2,3-triazoles in good yields showing high functional group compatibility.The reaction was effective for late-stage functionalization of bioactive molecules and^(18)F-trifluoromethylation of iodotriazoles.This work provides a practical synthetic methodology for the development of triazole drugs and^(18)F-radiotracers for positron emission tomography.
文摘Aryl azides and a-keto phosphorus ylides were reacted within 4 similar to 10 minutes with silica gel support, under microwave irridiation to afford corresponding 1-aryl-1, 2, 3-triazoles in moderate to good yields.
基金support from Natural Science Foundation of China and Shandong Province(Nos.22471143 and ZR2020QB012)the Taishan Scholar award of Shandong Province.
文摘A copper-catalyzed tandem click/amidation reaction involving various alkynes,azides,and dioxazolones has been developed for the synthesis of fully substituted 5-amide-1,2,3-triazoles.The key step in this reaction is the interception of the in situ-formed cuprate-triazole intermediate with N-acyl nitrenes,which are generated from dioxazolones.The choice of precursor for the N-acyl nitrenes plays a crucial role in the success of the reaction.This method is characterized by a broad substrate scope,mild reaction conditions,and complete regioselectivity.
基金the National Natural Science Foundation of China(Nos.21871235,21901230,21801224)the Natural Science Foundation of Zhejiang Province(No.LQ18B020009)+1 种基金the Fundamental Research Funds of Zhejiang Sci-Tech University(2019Y003)the Science Foundation of Zhejiang Sci-Tech University(ZSTU)under Grant No.18062301-Y is gratefully acknowledged.
文摘An efficient rhodium(Ⅱ)-catalyzed[4+3]cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed.Azepino[5,4,3-ccflindoles,which are widely distributed in ergot alkaloids with various biological activities,could be obtained in good to excellent yields.In addition,the total synthesis of(±)-aurantioclavine was completed in four steps from the known compound 1a adopting this[4+3]cyclization as a key step.
基金The authors acknowledge the financial support from the National Natural Science Foundation of China(Nos.22061040 and 21562039)the Xinjiang Provincial Natural Science Foundation of China(Nos.2022E01069 and 2020D01C024).
文摘Available online A mild and efficient photocatalytic-induced radical method has been developed for[4+1]cycloaddition reaction of 1,4-disubstituted 1,2,3-triazoles with N-tosylhydrazides and primary amines.The reaction is catalyzed by 20 mol%of I2 under metal,azide and oxidant-free conditions.The method is based upon the photocatalytic generation of allyl-type radicals,followed by the iodine-catalyzed production of azoalkenes,which react rapidly with various anilines.
文摘A Cul-catalyzed three-component coupling of trifluoromethyl ketone N-tosylhydrazones, alkynes and azides has been developed. The reaction represents a straightforward method to access difluoromethylene substituted 1,2,3-triazoles. Mechanistically, it has been proposed that the reaction follows a pathway involving the formation of Cu（1） triazolide intermediate, Cu（I） carbene formation, migratory insertion, and β-fluoride elimination. The trans- formation is featured by mild conditions, wide substrate scope and high efficiency.
基金supported by the National Natural Science Foundation of China(21172181,21372186,81450110094)the key program from Natural Science Foundation of Chongqing(CSTC2012jj B10026)+3 种基金the Specialized Research Fund for the Doctoral Program of Higher Education of China(SRFDP 20110182110007)the Doctoral Fund of Southwest University(SWU111075)the Research Funds for the Central Universities(XDJK2013C112)Chongqing Special Foundation for Postdoctoral Research Proposal(Xm201450)
文摘A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution. 2-Chlorobenzyl triazolium 8g and compound 9b with octyl group exhibited the best antibacterial activities among all the tested compounds, especially against S. aureus with inhibitory concentration of 2 μg/mL which was equipotent potency to Norfloxacin(MIC=2 μg/mL) and more active than Chloromycin(MIC=7 μg/mL). Triazoliums 8g and 8f bearing 3-fluorobenzyl moiety displayed the best antifungal activities(MIC=2-19 μg/mL) against all the tested fungal strains without being toxic to PC12 cell line within concentration of 128 μg/m L. Further investigations by fluorescence and UV-Vis spectroscopic methods revealed that the compound 8g could effectively intercalate into calf thymus DNA to form the 8g-DNA complex which could block DNA replication, exerting powerful antimicrobial activities.
基金Project supported by the National Natural Science Foundation of China (No. 20272075) and the National Natural Science Foundation of Zhejiang Province (No. M203001).
文摘Azido-3,5-dichloropyridine and 2-azido-5-chloro-3-fluoropyridine were given by reaction of sodium azide with 2,3,5-trichloropyridine, 3,5-dichloro-2-fluoropyridine or 5-chloro-2,3-difluoropyridine in ionic liquids. 1,3-Dipolar cycloaddition of 2-azido-3,5-dichloropyridine or 2-azido-5-chloro-3-fluoropyridine to alkynes in ionic liquids afforded the corresponding 1,4,5-trisubstituted [1,2,3]-triazoles in good yields and regioselectivities.
基金This work was supported by the NSFC(Grant 21772019)the Venture and Innovation Support Program for Chongqing Overseas Returnees(cx2019007 and cx2020047)。
文摘We here report a direct ring-opening/semipinacol rearrangement reaction of 4-(1-hydroxycyclobutyl)-1,2,3-triazole,in which N-acyl substituted 1,2,3-triazole was generated in situ and would trigger thermo-dynamically controlled electrocyclization ring-opening to afford a rearrangement precursor(α-diazo-ol).This strategy avoided the usage of metal catalysts and the reservation of sulfonyl groups on the N^(1)-posi-tion of 1,2,3-triazole.The final cycloenaminone product is highly reactive and could be commonly used as a dinucleophilic acceptor to synthesize structurally diverse fused bicyclic products.
基金the National Key Research and Development Program of China(2022YFD1700204)the Open Fund of State Key Laboratory of Green Pesticide by South China Agricultural University(gplscau202415)the National Natural Science Foundation of China(22477040).
文摘Currently,triazole sulfonamide fungicide could be used to effectively control cucumber downy mildew(CDM),caused by Pseudoperonospora cubensis.In this study,a series of triazole sulfonamide derivatives containing diphenyl ether(DE)fragment were designed and synthesized.All target compounds were evaluated for their fungicidal activity against four oomycete diseases.Compound 10b showed the best activity against CDM with 40%control efficacy at 0.78 mg/L,which was the same as amisulbrom.Meanwhile,compounds 10d and 10h showed good inhibitory activity against Peronophythora litchii and compounds 10e,10f,10l and 10q showed good inhibitory activity against Phytophthora infestans.The results of computational chemistry showed that compound 10b had the same binding mode as amisulbrom and formed hydrogen bonds with the residues Gln9,His189 and Ash217.Compound 10b could be further investigated as a potential fungicide candidate.This study also provides a useful optimization strategy for the design of novel fungicides against CDM.
文摘Seven podophyllotoxin analogues were synthesized by condensation of 4′ demethyl epipodophyllotoxin 10 with 5 alkyl 4 amino 3 mercapto 1,2,4 triazoles 9(a g) in the presence of TFA(CF 3COOH). Their antitumor activities were screened in vitro against HL 60 and K 562 cells.
基金supported by the Higher Education Commision(HEC),Govt.of Pakistan
文摘Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu（OAc）2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a（C10H9N5O4） crystallizes in the triclinic system, space group P1 with a = 5.0894（9）, b = 8.9834（13）, c = 13.089（2） ？, α= 83.041（7）, β= 80.256（7）, γ=87.296（8）°, V = 585.24（16）？3, Z = 2, Mr = 263.22, crystal size（mm） = 0.37 × 0.20 ×0.18,（I 〉 2σ（I）） = 8557, 2493, 1229, Rint = 0.057. Compound 1b（C12H13N5O4） crystallizes in the monoclinic system, space group P21/c with a = 6.8854（5）, b = 21.783（2）, c = 9.3986（8） ？,β = 93.239（4）°, V = 1407.4（2）？3, Z = 4, Mr = 291.27, crystal size（mm） = 0.38 × 0.22 × 0.20,（I 〉 2σ（I）） = 11842, 3172, 1866, Rint = 0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains.
文摘Ten new antifungal triazoles,3-sulfonanido-2-aryl-1-triazoly1-2-propanol derivatives were designed and synthesized as potential inhibitors of the fungal cytochrome P-45014a-demethylase.Results ofantifungal tests in vitro showed that compounds Ib,Ie and Ig had high activity,especially against Candida albicans.Candida parapsilosis and Fonsecaea pedrosor,but less active in comparison with ketoconazole.Compared withfluconazole,compound 1b was thirty-two times more active against Candida parapsilosis and four times more activeagainst Fonsecaea pedrosor;compound 1e was sixteen times more active against Candida parapsilosis and eighttimes more active against Fonsecaea pedrosor,compound lg was four times and eight times more active againstCandida parapsilosis and Fonsecaea pedrosor respectively.
文摘Eleven 1-(1H-1,2,4-triazole)-2-(2,4-diflurophenyl)-3-(N-methyl-N-substituted benzylamino)-2-propanols were designed and synthesized, on the basis of the crystal structure of P450 cytochrome 14α-sterol demethylase(CYP51) and the docking results of inhibitors to the active site of the enzyme. All title compounds were first by reported. Results of preliminary biological tests showed that most of title compounds exhibited activity against the seven common pathogenic fungi. Compound 11 showed best antifungal activity with broad antifungal spectrum and proved to be more active against Cryptococcus neoformans, Candida albicans, Microsporum lanosum and Trichophyton rubrum than ketoconazole. Compounds 3, 10 and 4 also had high activities.
