Sythesis Of 1-Deoxynojirimycin Modified Perylene Bisimide Derivatives And Their Multivalent Study Of Glucosidase Inhibition

Multivalent iminosugars has become a rapid developing topic in recent years.Multivalent glycosidase inhibitors were widely constructed through covalently,however the supramolecular multivalent glycosidase inhibitors were limited,especially for controlled multivalent glycosidase inhibitors.Based on the potent glycosidase activity of1-deoxynojirimycin（DNJ）derivatives,the excellent self-assembling properties and fluorescent properties of perylene bisimides and naphthalimide derivatives,a series of1-DNJ modified perylene bisimides（PBI-A,PBI-A-ion,PBI-L and PBI-D）and naphthalimide derivatives（ND-A and ND-C）were synthesized,and were fully charactized by NMR and HRMS analyses.Furthermore,the self-assembly behavior and host-guest controlled supramolecular multivalent glucosidase activity were studied.Theses results paied a new method for the multivalent glycosidase inhibitors.The main contents include:1)Compared with the methods reported in the previous references,a new synthesized method of 2,3,4,6-tetra-acetyl-1-DNJ derivatives was developed.Firstly,the2,3,4,6-tetra-benzyl-1-DNJ was removied the benzyl protecting group though catalytic hydrogenation,then 2,3,4,6-tetra-acetyl-1-DNJ was obtained by nucleophilic substitution reactions and acetylation reaction with the isolated yield of 30%.2)Four perylene bisimide derivatives（PBI-A,PBI-A-ion,PBI-L and PBI-D）and two1-DNJ modified naphthalimide derivatives were synthesized,and were fully characterized by¹H NMR,¹³C NMR and HRMS analyses.3)The aggregation properties and host-guest controlled supramolecular multivalent glycosidase inhibitors with CB[8]and Amantadine were investigated by UV-Vis and fluorescence spectra.This results indicated that multivalent assembly showed high binding interactions with glycosidase than the mono-molecule.