Synthesis And Characterization Of Salidroside Analogues,and The Study On The Inhibition To Tyrosinase Activity

Salidroside is a perennial of rare medicinal plants in one of the most important components of Rhodiola rosea L.,salidroside has a very wide range of drugs,for example:ease fatigue,enhance immunity,improve resistance hypothermia,removal of free radicals,protecting the hear and brain blood vessels and so on.Analogue of salidroside and have different substituents on the benzene ring or connect different types of sugar and salidroside may make similar property change of life.Analogues of salidroside in the field of drug development and application has attracted more and more attention from researchers.This paper under the flatten principle,coupling with different sugars and analogues of tyrosol.Obtains a series of analogues of Salidroside.The synthesis of salidroside and tyrosol analogues were studied by tested the inhibition to tyrosinase activity,in order to get better whitening compound.There are three parts in this dissertation:First part:Introduce the research progress of Rhodiola rosea L.,salidroside and analogues of salidroside.Describe the application in the field of medicine and pharmacological of salidroside and analogs of salidroside.described the analogues of salidroside prospects for development.Second part:Describes analogues of salidroside on the design,synthesis and characterization of structure.A total of 44 compounds were synthesized,in which 33compounds not reported,as follows:1.Using different substituted benzyl cyanide as raw materials,through hydrolysis,esterification and restore.Finally we get a total of 16 important intermediates[R-1d?R-2d?R-2(b-c)?R-4(d-e)?R-1h?R-2h?R-4h?R-1i?R-2i?R-4(i-j)?R-2j?R-4(l-m)]and 4 different analogues of tyrosol[R-3d?R-3h?R-3(i-j)].2.Combination of tyrosol analogues and tetra-O-acetyl-a-D-glucopyranosyl bromide,and then remove the acetyl group and the benzyl protecting groups.Finally we get 4 salidroside analogues[R-4(a-c)?R-5d].3.Combination of tyrosol analogues and tetra-O-acetyl-a-D-galactopyranosyl bromide,and then remove the acetyl group and the benzyl protecting groups.Finally we get 6 salidroside analogues[R-5e?R-4(f-g)?R-5(h-j)].4.Combination of tyrosol analogues and tetra-O-acetyl-a-D-mannopyranose bromide,and then remove the acetyl group and the benzyl protecting groups.Finally we get 3 salidroside analogues[R-4k?R-5(l-m)].The 33 synthesis of new compounds were characterized by IR and ~1H NMR.Third part:The synthesis of salidroside and tyrosol analogues were studied by tested the inhibition to tyrosinase activity.The study shows that R-3c and R-5j have significant inhibition to tyrosinase.However,R-1c?R-1j?R-1g?R-3b?R-3h?R-3i?R-4b and R-4l inhibition to tyrosinase activity was weaker than the positive control substance of?-Arbutin.