Synthesis and immunostimulating activity of C -pseudonucleosides containing N -phenyl thiazolidin-4-one

Several novel C -pseudonucleosides containing N -phenyl thiazolidin-4-one were synthesized at room temperature using the unprotected sugar aldehyde as the starting material. The effects of the compounds on Con A-induced T cell proliferation were evaluated at five concentrations of 5, 10, 25, 50, and 100 μM. Some compounds, such as 5d , 5e , 5f , and 4g could significantly increase the proliferation by 62, 63, 70, and 53 % at low concentration of 5 μM, respectively. The structure–activity relationship indicated that the lipophilicity substituents like chloro atom, methyl, and methoxyl on the para position of N-3 phenyl at the thiazolidin-4-one ring had a detrimental impact on the T cell proliferation. The C-2 configuration and the electronic property of the lipophilicity substituents likely had slight effects on the immunostimulatory activities of such C -pseudonucleosides.