کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1355610 | 1500456 | 2015 | 7 صفحه PDF | دانلود رایگان |
• Synthesis of seven new polyhydroxylated azepanes was carried out.
• Cis- and trans-diols were obtained from an unsaturated azepane.
• Determination of the configurations was achieved for each compound by NMR and X-ray diffraction.
• Azepanes were assayed for their inhibitory activity toward a range of six commercially available glycosidases.
• A selective and good inhibition of β-galactosidase was obtained for one polyhydroxylated azepane.
A series of diastereomeric tetrahydroxylated azepanes featuring a carboxymethyl group at the pseudo-anomeric position have been synthesized from a common unsaturated intermediate. Syn- and anti-dihydroxylation reactions were achieved to yield the target compounds after efficient one-step deprotection of carbamate, ester and acetonide groups simultaneously. Screening of these polyhydroxylated azepanes toward a range of commercially available glycosidases was performed and one of the stereoisomers showed potent and selective inhibition toward β-galactosidase (IC50 = 21 μM).
Figure optionsDownload as PowerPoint slide
Journal: Bioorganic Chemistry - Volume 58, February 2015, Pages 11–17