CuAAC click chemistry with N-propargyl 1,5-dideoxy-1,5-imino-D-gulitol and N-propargyl 1,6-dideoxy-1,6-imino-D-mannitol provides access to triazole-linked piperidine and azepane pseudo-disaccharide iminosugars displaying glycosidase inhibitory properties
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- 作者：Luí ; s Otá ; vio B. Zamonera ; Valquí ; ria Aragã ; o-Leonetia ; Susimaire P. Mantoania ; Michael D. Rugenb ; Sergey A. Nepogodievb ; Robert A. Fieldb ; Ivone Carvalhoa ; carronal@usp.br" class="auth_mail" title="E-mail the corresponding author
- 关键词：Pseudo-disaccharide iminosugars ; CuAAC reaction ; Click chemistry ; Glycosidase inhibition
- 刊名：Carbohydrate Research
- 出版年：2016
- 出版时间：24 June 2016
- 年：2016
- 卷：429
- 期：Complete
- 页码：29-37
- 全文大小：987 K
文摘
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Eight triazole-linked piperidine and azepane pseudo-disaccharide iminosugars were synthesized from 1,2:5,6-di-anhydro-D-mannitol scaffold using click chemistry approach.
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Interesting α-glucosidase inhibition (53 µM) was achieved for one of the piperidine-iminosugar with inverted configuration at C-2 and C-5 with respect to DNJ (180 µM).
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Molecular modeling studies showed binding interactions of (15) and (17) with both glucosidase catalytic aa (Glu771 and Asp568), while the less potent (16) which interacted with Glu771.