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.
Zhou
Jian
J
The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road #38, Beijing 100083, PR China.
Zhang
Yongmin
Y
Zhou
Xia
X
Zhou
Jing
J
Zhang
Li-He
LH
Ye
Xin-Shan
XS
Zhang
Xiao-Lian
XL
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