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

作　　者：Hua Chen Shun-Kai Xing Fang Gao Na Li Xiao-Liu Li Ming Meng 

机构地区：[1]Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University [2]Medical School, Hebei University

出　　处：《Chinese Chemical Letters》2016年第6期938-942,共5页中国化学快报（英文版）

基　　金：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);the Natural Science Foundations of Education Department of Hebei (No. ZH2011110)

摘　　要：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 5 b 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.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 5 b 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.

关 键 词：IMMUNOMODULATOR C-Pseudonucleosides Thiazolidin-4-one Acetamide bond SAR analysis 

分 类 号：O626[理学—有机化学]