Design and synthesis of iso-allo-DNJ and l-isoDALDP derivatives: pursuit of potent and selective inhibitors of α-glucosidase - Details

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A　series　of　iso-allo-DNJ　and　l-isoDALDP　derivatives　were　synthesized　from　dithioacetal　16　with　sequential　and　highly　diastereoselective　Ho　and　Henry　reactions,　and　aziridinium　intermediate-mediated　ring　rearrangement　as　key　steps.　Glycosidase　inhibition　assay　found　four　of　them　as　selective　α-glucosidase　inhibitors,　and　the　less　substituted　compound　30　showed　more　potent　α-glucosidase　inhibition　(IC50　=　9.3　μM)　than　the　others.　Molecular　docking　study　revealed　different　docking　modes　of　the　iso-allo-DNJ　and　l-isoDALDP　derivatives　from　their　parent　compounds,　and　also　the　similarity　of　compound　30　to　isofagomine.　©　2023　The　Royal　Society　of　Chemistry.

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[ 1 ] [Yang L.-F.]Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
[ 2 ] [Yang L.-F.]High School Attached to Beijing University of Technology, Beijing, 100022, China
[ 3 ] [Zhang M.]Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
[ 4 ] [Zhang M.]University of Chinese Academy of Sciences, Beijing, 100049, China
[ 5 ] [Shimadate Y.]Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan
[ 6 ] [Kato A.]Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan
[ 7 ] [Hou T.L.]Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
[ 8 ] [Hou T.L.]University of Chinese Academy of Sciences, Beijing, 100049, China
[ 9 ] [Li Y.-X.]Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
[ 10 ] [Li Y.-X.]University of Chinese Academy of Sciences, Beijing, 100049, China
[ 11 ] [Jia Y.-M.]Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
[ 12 ] [Jia Y.-M.]University of Chinese Academy of Sciences, Beijing, 100049, China
[ 13 ] [Fleet G.W.J.]Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom
[ 14 ] [Yu C.-Y.]Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
[ 15 ] [Yu C.-Y.]University of Chinese Academy of Sciences, Beijing, 100049, China

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Organic and Biomolecular Chemistry

ISSN： 1477-0520

Year： 2023

Issue： 16

Volume： 21

Page： 3453-3464

3 . 2 0 0

JCR@2022

ESI Discipline： BIOLOGY & BIOCHEMISTRY;

ESI HC Threshold：16

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