研究了四氢吡咯并[3,4-c]吡咯-1,3-二酮经N-炔丙基化反应,铜催化的Huisgen[3+2]环加成和N-芳基化串联反应一步法合成三氮唑苯二氮卓化合物的新方法。产物经熔点仪、质谱、1 H NMR和13 C NMR进行了表征。该方法原料易得、操作简单、反应...研究了四氢吡咯并[3,4-c]吡咯-1,3-二酮经N-炔丙基化反应,铜催化的Huisgen[3+2]环加成和N-芳基化串联反应一步法合成三氮唑苯二氮卓化合物的新方法。产物经熔点仪、质谱、1 H NMR和13 C NMR进行了表征。该方法原料易得、操作简单、反应条件温和、产物收率高。展开更多
Thermally stable polymers containing 1,3,4-oxadiazole units have been synthesized through Huisgen reaction of the aromatic/aliphatic bis-tetrazole compounds with the aromatic/aliphatic bis-acid chlorides in pyridine a...Thermally stable polymers containing 1,3,4-oxadiazole units have been synthesized through Huisgen reaction of the aromatic/aliphatic bis-tetrazole compounds with the aromatic/aliphatic bis-acid chlorides in pyridine as solvent.The obtained polymers are insoluble or slightly soluble even in polar aprotic solvents such as DMSO and DMF.Relatively high inherent viscosity values（0.61-1.33 dL/g,in 0.125%H_2SO_4 at 25℃） were observed for these compounds.Thermal analyses of the polymers using DSC and TGA techniques showed that the polymers have improved thermal stabilities.The glass transition temperature has not been observed in the fully aromatic polymers,but the polymers obtained from 5-[6-（1H-tetrazol -5-yl）hexyl]-lH-tetrazole（Ⅳ） showed very clear T_g.A model reaction was also investigated and the resulting bis-1,3,4-oxadiazole compound was characterized by conventional spectroscopy methods.展开更多
An efficient and green copper（Ⅱ） acetylacetonate-catalyzed protocol for the Huisgen-click reaction in water at 100℃ has been established. The protocol was not only suitable for the reaction between organic azides ...An efficient and green copper（Ⅱ） acetylacetonate-catalyzed protocol for the Huisgen-click reaction in water at 100℃ has been established. The protocol was not only suitable for the reaction between organic azides and alkynes, but also suitable for one-pot three-component reaction among alkyl halides, NaN3 and alkynes.展开更多
In the present work, new thermally stable polymers containing 1,3,4-oxadiazole units have been synthesized through Huisgen reaction of the aromatic bis-tetrazole compounds with the aromatic/aliphatic bis-acid chloride...In the present work, new thermally stable polymers containing 1,3,4-oxadiazole units have been synthesized through Huisgen reaction of the aromatic bis-tetrazole compounds with the aromatic/aliphatic bis-acid chlorides in pyridine as solvent. The obtained polymers are insoluble or slightly soluble in polar aprotic solvents such as DMSO and DMF. Thermal analyses of the polymers using DSC and TGA techniques showed that the polymers had improved thermal stabilities. The model reaction was also investigated and the resulting bis-1,3,4-oxadiazole compounds were characterized by conventional spectroscopic methods.展开更多
Objective: To obtain suitable artimisinin-based drug candidates with high antimalarial activity.Methods: Three different reaction schemes were used to synthesize a total of 15 artemisininbased compounds.The first synt...Objective: To obtain suitable artimisinin-based drug candidates with high antimalarial activity.Methods: Three different reaction schemes were used to synthesize a total of 15 artemisininbased compounds.The first synthetic scheme involved the synthesis of diazido aliphatic and aromatic compounds from commercially available dihalides and azido derivatives of artemisinin.The second scheme consisted of the reaction of dibromoaliphatic compounds with sodium azide in dimethylformamide which yielded the desired compounds.Artemisinin-based compounds on treatment with sodium azide and bromotrimethylsilane in dichloromethane produced the most potent compound GB-2.Another potent compound GB-1 was synthesized from artemisinin by treatment with alcohols in the presence of Aberlyst-15 in anhydrous dichloromethane.The third scheme involved the Huisgen 1,3-dipolar cycloaddition between the synthesized aliphatic and aromatic diazides and two alkyne derivatives of artemisinin to obtain the desired artemisinin dimers with average yields.Results: The best in vitro antiplasmodial activity was shown by the compound GB-2 registering IC_(50) value 0.066 μg/mL against chloroquine-sensitive and 0.865 μg/mL against chloroquineresistant strains of Plasmodium falciparum.It suppressed 59.0% parasitaemia in vivo of rodent malaria parasite Plasmodium berghei in Swiss albino model at 50 μg/kg body weight dosage.Molecular docking interactions of Plasmodium falciparum ATP6(PfATP6) protein revealed strong bonding of GB-2 with Thr255 residue which is likely to be the reason for excellent antimalarial activity of this compound.Conclusion: Two compounds GB-1 and GB-2 exhibited excellent in vitro antiplasmodial activity and fair in vivo antimalarial activity.Of the two, GB-2 showed better activity which could be attributed to its strong bonding interactions with Thr255 as evidenced from the molecular docking study.Study helped in identifying artemisinin analogues possessing good antimalarial properties and further research in structural alterations of the selected molecules should be carried out which may result in obtaining potent drug candidates against the malarial parasite.展开更多
Carboxymethyl glycoside lactones(CMGLs) are bicyclic synthons which open readily for accessing new types of pseudo-glycoconjugates,such as sugar-amino acid hybrids,neoglycolipids,pseudodisaccharides,and membrane imagi...Carboxymethyl glycoside lactones(CMGLs) are bicyclic synthons which open readily for accessing new types of pseudo-glycoconjugates,such as sugar-amino acid hybrids,neoglycolipids,pseudodisaccharides,and membrane imaging systems.After lactone opening,free OH-2 is available for further functionalization,leading to 1,2-bisfunctionalized derivatives.This strategy is illustrated herein with new polymerizable systems of the AB type bearing both azide and alkyne functions prepared from α or β gluco-CMGL synthons.After the reaction of lactones with propargylamine,an azido group was introduced by two different sequences leading to either the 2-manno-azido or the 6-gluco-azido products.The capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition(CuAAC) and generate glycopolytriazoles was evidenced.展开更多
A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cyeloaddition between 4,6-dimethoxy-2-[（4-prop-2-ynyl）piperazin-l-yl]pyrimidine and each of...A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cyeloaddition between 4,6-dimethoxy-2-[（4-prop-2-ynyl）piperazin-l-yl]pyrimidine and each of different azides catalysed by in situ generated Cu（I）. The O-acyl protecting groups on glycosyl 1,2,3-triazoles were removed by triethylamine in wet methanol. Their chemical structures were established on the basis of corresponding tH NMR, 13C NMR, MS and elemental analysis. The fungicidal activities of target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Phytophthora capsici, Cercospora arachi- dicola and Gibberella zeae at 50 μg/mL. The bioassay results indicate that some of the compounds exhibited mode- rate but promising fungicidal activities. In particular, acetylated glucopyranosyl triazole displayed a good fungicidal activity against Physalospora piricola, which is equal to that of the positive control compound chlorothalonil.展开更多
基金Supported by National Natural Science Foundation of China(20872001)the Natural Science Foundation of Education Administration of Anhui Province(KJ2008A064)
基金financially supported by the Research Council of the University of Mohaghegh Ardabili(Iran)
文摘Thermally stable polymers containing 1,3,4-oxadiazole units have been synthesized through Huisgen reaction of the aromatic/aliphatic bis-tetrazole compounds with the aromatic/aliphatic bis-acid chlorides in pyridine as solvent.The obtained polymers are insoluble or slightly soluble even in polar aprotic solvents such as DMSO and DMF.Relatively high inherent viscosity values（0.61-1.33 dL/g,in 0.125%H_2SO_4 at 25℃） were observed for these compounds.Thermal analyses of the polymers using DSC and TGA techniques showed that the polymers have improved thermal stabilities.The glass transition temperature has not been observed in the fully aromatic polymers,but the polymers obtained from 5-[6-（1H-tetrazol -5-yl）hexyl]-lH-tetrazole（Ⅳ） showed very clear T_g.A model reaction was also investigated and the resulting bis-1,3,4-oxadiazole compound was characterized by conventional spectroscopy methods.
文摘An efficient and green copper（Ⅱ） acetylacetonate-catalyzed protocol for the Huisgen-click reaction in water at 100℃ has been established. The protocol was not only suitable for the reaction between organic azides and alkynes, but also suitable for one-pot three-component reaction among alkyl halides, NaN3 and alkynes.
基金supported by the Graduate Council of University of Mohaghegh Ardabili(Iran)
文摘In the present work, new thermally stable polymers containing 1,3,4-oxadiazole units have been synthesized through Huisgen reaction of the aromatic bis-tetrazole compounds with the aromatic/aliphatic bis-acid chlorides in pyridine as solvent. The obtained polymers are insoluble or slightly soluble in polar aprotic solvents such as DMSO and DMF. Thermal analyses of the polymers using DSC and TGA techniques showed that the polymers had improved thermal stabilities. The model reaction was also investigated and the resulting bis-1,3,4-oxadiazole compounds were characterized by conventional spectroscopic methods.
基金financial support as an intramural activity provided by Director, ICMR- Regional Medical Research Centre, Dibrugarh (Assam), India for the study is gratefully acknowledged
文摘Objective: To obtain suitable artimisinin-based drug candidates with high antimalarial activity.Methods: Three different reaction schemes were used to synthesize a total of 15 artemisininbased compounds.The first synthetic scheme involved the synthesis of diazido aliphatic and aromatic compounds from commercially available dihalides and azido derivatives of artemisinin.The second scheme consisted of the reaction of dibromoaliphatic compounds with sodium azide in dimethylformamide which yielded the desired compounds.Artemisinin-based compounds on treatment with sodium azide and bromotrimethylsilane in dichloromethane produced the most potent compound GB-2.Another potent compound GB-1 was synthesized from artemisinin by treatment with alcohols in the presence of Aberlyst-15 in anhydrous dichloromethane.The third scheme involved the Huisgen 1,3-dipolar cycloaddition between the synthesized aliphatic and aromatic diazides and two alkyne derivatives of artemisinin to obtain the desired artemisinin dimers with average yields.Results: The best in vitro antiplasmodial activity was shown by the compound GB-2 registering IC_(50) value 0.066 μg/mL against chloroquine-sensitive and 0.865 μg/mL against chloroquineresistant strains of Plasmodium falciparum.It suppressed 59.0% parasitaemia in vivo of rodent malaria parasite Plasmodium berghei in Swiss albino model at 50 μg/kg body weight dosage.Molecular docking interactions of Plasmodium falciparum ATP6(PfATP6) protein revealed strong bonding of GB-2 with Thr255 residue which is likely to be the reason for excellent antimalarial activity of this compound.Conclusion: Two compounds GB-1 and GB-2 exhibited excellent in vitro antiplasmodial activity and fair in vivo antimalarial activity.Of the two, GB-2 showed better activity which could be attributed to its strong bonding interactions with Thr255 as evidenced from the molecular docking study.Study helped in identifying artemisinin analogues possessing good antimalarial properties and further research in structural alterations of the selected molecules should be carried out which may result in obtaining potent drug candidates against the malarial parasite.
基金Financial support from CNRS and MESER is gratefully acknowledged, as well as a fellowship from Chinese Scholarship Council to CHEN Jie
文摘Carboxymethyl glycoside lactones(CMGLs) are bicyclic synthons which open readily for accessing new types of pseudo-glycoconjugates,such as sugar-amino acid hybrids,neoglycolipids,pseudodisaccharides,and membrane imaging systems.After lactone opening,free OH-2 is available for further functionalization,leading to 1,2-bisfunctionalized derivatives.This strategy is illustrated herein with new polymerizable systems of the AB type bearing both azide and alkyne functions prepared from α or β gluco-CMGL synthons.After the reaction of lactones with propargylamine,an azido group was introduced by two different sequences leading to either the 2-manno-azido or the 6-gluco-azido products.The capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition(CuAAC) and generate glycopolytriazoles was evidenced.
基金Supported by the National Basic Research Program of China（No.2010CB126106）, the Fundamental Research Funds for the Central Universities and Natural Science Foundation of China（No.31000861）.
文摘A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cyeloaddition between 4,6-dimethoxy-2-[（4-prop-2-ynyl）piperazin-l-yl]pyrimidine and each of different azides catalysed by in situ generated Cu（I）. The O-acyl protecting groups on glycosyl 1,2,3-triazoles were removed by triethylamine in wet methanol. Their chemical structures were established on the basis of corresponding tH NMR, 13C NMR, MS and elemental analysis. The fungicidal activities of target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Phytophthora capsici, Cercospora arachi- dicola and Gibberella zeae at 50 μg/mL. The bioassay results indicate that some of the compounds exhibited mode- rate but promising fungicidal activities. In particular, acetylated glucopyranosyl triazole displayed a good fungicidal activity against Physalospora piricola, which is equal to that of the positive control compound chlorothalonil.
