Aim To develop a concise method for the synthesis of bicyclic azasugar and thiosugar with novel scaffold. Methods The two primary hydroxyl groups of compound 1 were selectively protected with tosyl cloloride in pyridi...Aim To develop a concise method for the synthesis of bicyclic azasugar and thiosugar with novel scaffold. Methods The two primary hydroxyl groups of compound 1 were selectively protected with tosyl cloloride in pyridine, followed by ring-closure with sodium sulfide or primary amine to form the oxy-bridged bicyclic molecules in good yields. Results Two bicyclic azasugars and a thiosugar were produced from L-sorbose in several steps. Conclusion The described procedures provide an efficient method to synthesize bicyclic azasugar and thiosugar with novel scaffold as potential glycosidase inhibitors.展开更多
A series of novel, azasugar-modified 2-monosubstituted, 2,6- and 2,7-bissubstituted anthraquinone derivatives have been synthesized by the nucleophilic substitution of N-alkylamino azasugar with mono-, bis（2-chloroac...A series of novel, azasugar-modified 2-monosubstituted, 2,6- and 2,7-bissubstituted anthraquinone derivatives have been synthesized by the nucleophilic substitution of N-alkylamino azasugar with mono-, bis（2-chloroacetamido）anthraquinones. Their cytotoxic activities against HeLa and MCF-7 ceils were preliminarily evaluated and compound 9a with mono-azasugar pendant at 2-position showed similar activity to the control drug （Cisplatin）.展开更多
A novel C-branched polyhydroxylated cyclic nitrone 25.which could be a valuable intermediate for the synthesis of C-branched pyrrolidine iminosugars,was synthesized starting from the commercially available i.-arabinos...A novel C-branched polyhydroxylated cyclic nitrone 25.which could be a valuable intermediate for the synthesis of C-branched pyrrolidine iminosugars,was synthesized starting from the commercially available i.-arabinose in 29.0%total yield.展开更多
N-butyl-1-deoxynojirimycin(Zavesca) is an important glucosidase inhibitor,which is a kind of azasugar,which is synthesized from glucose,followed by oxidation,amination,reduction and deprotection etc.The structure of t...N-butyl-1-deoxynojirimycin(Zavesca) is an important glucosidase inhibitor,which is a kind of azasugar,which is synthesized from glucose,followed by oxidation,amination,reduction and deprotection etc.The structure of target compound is confirmed by 1H NMR.展开更多
A catalytic two-component three-centered(2C3C)Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin(DNJ)isomers using a chiron approach.This new and quite mild catalytic system,comprised of phenylp...A catalytic two-component three-centered(2C3C)Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin(DNJ)isomers using a chiron approach.This new and quite mild catalytic system,comprised of phenylphosphinic acid/Nal,was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.展开更多
基金We thank the National Science Foundation of China(NSFC,N0.20372003)for financial support.
文摘Aim To develop a concise method for the synthesis of bicyclic azasugar and thiosugar with novel scaffold. Methods The two primary hydroxyl groups of compound 1 were selectively protected with tosyl cloloride in pyridine, followed by ring-closure with sodium sulfide or primary amine to form the oxy-bridged bicyclic molecules in good yields. Results Two bicyclic azasugars and a thiosugar were produced from L-sorbose in several steps. Conclusion The described procedures provide an efficient method to synthesize bicyclic azasugar and thiosugar with novel scaffold as potential glycosidase inhibitors.
基金supported by the National Natural Science Foundation of China(Nos.21372059 and 21172051)the Hebei Key Basic Research(No.12966417D)+1 种基金the Hebei Natural Science Foundation(No.B2012201041)the Foundation of Hebei Education Department(No.YQ2013006)
文摘A series of novel, azasugar-modified 2-monosubstituted, 2,6- and 2,7-bissubstituted anthraquinone derivatives have been synthesized by the nucleophilic substitution of N-alkylamino azasugar with mono-, bis（2-chloroacetamido）anthraquinones. Their cytotoxic activities against HeLa and MCF-7 ceils were preliminarily evaluated and compound 9a with mono-azasugar pendant at 2-position showed similar activity to the control drug （Cisplatin）.
基金Financial support from National Basic Research Program of China(No.2012CB822101)the National Natural Science Foundation of China(No.21272240)+1 种基金National Science and Technology Major Projects for "Major New Drugs Innovation and Development"(No.2013ZX09508104)National Engineering Research Center for Carbohydrate Synthesis of Jiangxi Normal University
文摘A novel C-branched polyhydroxylated cyclic nitrone 25.which could be a valuable intermediate for the synthesis of C-branched pyrrolidine iminosugars,was synthesized starting from the commercially available i.-arabinose in 29.0%total yield.
文摘N-butyl-1-deoxynojirimycin(Zavesca) is an important glucosidase inhibitor,which is a kind of azasugar,which is synthesized from glucose,followed by oxidation,amination,reduction and deprotection etc.The structure of target compound is confirmed by 1H NMR.
文摘A catalytic two-component three-centered(2C3C)Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin(DNJ)isomers using a chiron approach.This new and quite mild catalytic system,comprised of phenylphosphinic acid/Nal,was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.
