An expeditious one-pot synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives and their inhibitory effects on the secretion of IFN-gamma and IL-4.
An efficient 'one-pot' approach to the synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives in good yields and with high stereoselectivity was developed. It was found that the synthetic N-alkylated iminosugars showed inhibitory effects on the release of the cytokines IFN-gamma and IL-4 from the mouse splenocytes. The preliminary structure-activity relationship was deduced from the activities of N-substituted iminosugars. Apart from the cytokine inhibitory activities, a series of glycosidase inhibitory activities were also examined. The present experimental data demonstrated that synthetic iminosugars might hold potential as immunosuppressive agents.
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road #38, Beijing 100083, PR China.
Jian
J
Zhou
Yongmin
Y
Zhang
Xia
X
Zhou
Jing
J
Zhou
Li-He
LH
Zhang
Xin-Shan
XS
Ye
Xiao-Lian
XL
Zhang
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D002478:Cells, Cultured; D007371:Interferon-gamma / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015847:Interleukin-4 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D051379:Mice; D013154:Spleen / Q000166:cytology; D013329:Structure-Activity Relationship; D013393:Sucrase / Q000037:antagonists & inhibitors
D017485:1-Deoxynojirimycin; D015847:Interleukin-4; D007371:Interferon-gamma; D013393:Sucrase; C013626:nojirimycin