Synthesis of Pyrrolidine Monocyclic Analogues of Pochonicine and Its Stereoisomers: Pursuit ofSimplified Structures and Potent β-

Xin Yan, Yuna Shimadate, Atsushi Kato, Yi-Xian Li, Yue-Mei Jia, George W J Fleet, Chu-Yi Yu

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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3 · Its place in the literature

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1 citing paper in PubMed.

Multivalent Pyrrolidine Iminosugars: Synthesis and Biological Relevance.Molecules (Basel, Switzerland) · 2022
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5 · Who and what money

Authors and funding

7 authors.

Xin YanBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Yuna ShimadateDepartment of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.

Atsushi KatoDepartment of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.

Yi-Xian LiBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Yue-Mei JiaBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

George W J FleetChemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX13TA, UK.

Chu-Yi YuBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Ten pairs of pyrrolidine analogues of pochonicine and its stereoisomers have been synthesized from four enantiomeric pairs of polyhydroxylated cyclic nitrones. Among the ten N-acetylamino pyrrolidine analogues, only compounds with 2,5-dideoxy-2,5-imino-d-mannitol (DMDP) and pochonicine (1) configurations showed potent inhibition of β-N-acetylhexosaminidases (β-HexNAcases); while 1-amino analogues lost almost all their inhibitions towards the tested enzymes. The assay results reveal the importance of the

Indexed as

Animalsbeta-N-AcetylhexosaminidasesCyclizationEnzyme InhibitorsGlycoside HydrolasesPyrrolidinesPyrrolizidine AlkaloidsRatsStereoisomerism5-acetamidomethyl-3-hydroxymethyl-1,6,7-trihydroxypyrrolizidinebeta-N-AcetylhexosaminidasesEnzyme InhibitorsGlycoside HydrolasespyrrolidinePyrrolidinesPyrrolizidine AlkaloidsiminosugarspharmacophorePochonicinestructure-activity relationshipsynthesisβ-N-acetylhexosaminidase

Identifiers

PMID32218360

DOI10.3390/molecules25071498

PMCPMC7180638

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