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Citation: Hua Chen, Shun-Kai Xing, Fang Gao, Na Li, Xiao-Liu Li, Ming Meng. Design, synthesis and immunomodulating activity of C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond[J]. Chinese Chemical Letters, ;2016, 27(6): 938-942. doi: 10.1016/j.cclet.2016.01.041 shu

Design, synthesis and immunomodulating activity of C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond

Hua Chen ^a, ,
Shun-Kai Xing ^a ,
Fang Gao ^a ,
Na Li ^b ,
Xiao-Liu Li ^a ,
Ming Meng ^b

a Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China;
b Medical School, Hebei University, Baoding 071002, China

Received Date: 2 November 2015
Revised Date: 3 December 2015

Fund Project: The financial supports from the National Natural Science Foundation of China (Nos. 20972039, 21372060), Research Fund for the Doctoral Program of Higher Education of China (No. 20121301110004), Hebei Province Natural Science Fund for Distinguished Young Scholars (No. B2015201005), the Medicinal Joint Funds of the Natural Science Foundation of Hebei and Shijiazhuang Pharmaceutical Group Foundation (No. B2011201169), and the Natural Science Foundations of Education Department of Hebei (No. ZH2011110).

Several novel C-pseudonucleosides containing thiazolidin-4-one and phenyl connected by acetamide bond were rationally designed and easily synthesized at room temperature by 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 mmol/L Interestingly, compounds 7a and 8a (n = 2, R = H) exhibited immunostimulating activities, while compounds 5a, 6a (n = 1, R = H) and 7b, 8b (n = 2,R = CH₃) showed immunosuppressive activities. Another two compounds 5b and 6b (n = 1,R = CH3) had no immunomodulating activities. These initial biological results suggested that subtle structural changes to the phenyl and acetamide bond of C-pseudonucleosides could have a significant effect on T cell proliferation bias, although it was difficult to formulate a rigorous structureactivity relationship based on the observed activities.
- Immunomodulator,
- C-Pseudonucleosides,
- Thiazolidin-4-one,
- Acetamide bond,
- SAR analysis
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