Two kinds of free‐base tailed porphyrins modified with 2‐chloronicotinic acid and the corresponding Zn porphyrins have been synthesized. They have been characterized by elemental analysis and NMR, UV/Vis, fluorescence spectra, and infrared spectroscopies. Their configurations have been optimized through theoretical calculations. The fluorescence quantum yields were determined by a comparative method. The interactions between the Zn porphyrins and human serum albumin have been studied by means of fluorescence spectra. The experimental results showed that the interaction mechanism involved a combined fluorescence quenching process (static and dynamic quenching) and that the main driving force was hydrophobic in nature. Quenching constants, binding constants, thermodynamic parameters, and binding distances have been determined.

Eight novel quercetin conjugates 20～27 were successfully synthesized through a concise procedure with 15%～ 46% overall yields by using Rutin as the starting material. After O-benzylation, glycoside hydrolysis and O-propargylation, rutin was converted to the key intermediate 5,7,3',4'-tetrabenzyloxy-3-O-propargylquercetin, which subsequently 'clicked' with azido containing glycosides, poly(ethylene glycol) (PEG) or oligo(ethylene glycol) (OEG) to provide the fully protected quercetin conjugates 12～19. After global deprotection, the resulting quercetin conjugates were evaluated on hypoglycemic activities at 3T3-L1 adipocyte level. The results showed that conjugates 24, 26 and 27 exhibited good hypoglycemic effects.