A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.
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http://dx.doi.org/10.1016/j.carres.2015.02.014 | DOI Listing |
Inorg Chem
January 2025
Department of Chemistry, University College of Science, University of Calcutta, 92 A.P.C. Road, Kolkata 700009, India.
The well-known inhibitory strength of 3d metal Schiff base complexes against urease enzymes has long been acknowledged, but their untapped potential to act as ureolytic mimics of active metallobiosites remained unexplored. To break the new ground, we present pyrrolidine-based mononuclear Ni(II)-azide complex {[NiL(HL)(N)]·1.5(HO)} using the N,N,O donor ligand, namely ()-4-bromo-2-(((2-(pyrrolidin-1-yl)ethyl)imino)methyl)phenol.
View Article and Find Full Text PDFMolecules
November 2024
Anhui Key Laboratory of Bioactivity of Natural Products, School of Pharmacy, Anhui Medical University, Hefei 230032, China.
The herb (Lour.) Ktze is widely distributed in southern and southwestern China. The genus and its primary chemical constituents exhibit remarkable antidepressant activities.
View Article and Find Full Text PDFRSC Adv
October 2024
Department of Pharmacy, Riyadh Security Forces Hospital, Ministry of Interior Kingdom of Saudi Arabia.
Diabet Med
December 2023
Institute of Metabolism and Systems Research (IMSR), and Centre of Membrane Proteins and Receptors (COMPARE), University of Birmingham, Birmingham, UK.
We previously developed, synthesized and tested light-activated sulfonylureas for optical control of K channels and pancreatic beta cell activity in vitro and in vivo. Such technology relies on installation of azobenzene photoswitches onto the sulfonylurea backbone, affording light-dependent isomerization, alteration in ligand affinity for SUR1 and hence K channel conductance. Inspired by molecular dynamics simulations and to further improve photoswitching characteristics, we set out to develop a novel push-pull closed ring azobenzene unit, before installing this on the sulfonylurea glimepiride as a small molecule recipient.
View Article and Find Full Text PDFJ Nat Prod
May 2023
School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia.
The 10 glyphaeaside alkaloids isolated from the roots of were originally purported as piperidine-based 1--alkylated iminosugars, with the A-, B-, and C-type glyphaeasides bearing l-DFJ, DGJ, and DNJ ring configurations, respectively. Subsequent investigations have revealed glyphaeaside C as being a pyrrolidine-based iminosugar with a DMDP ring configuration via total synthesis of the revised structure. In this work, side chain diastereomers of the originally purported structure of glyphaeaside C () and two related α-1--alkylated DNJ derivatives were synthesized from a common precursor, which was prepared in turn via stereoselective Grignard addition to a protected d-glycosylamine, followed by a reductive amination-cyclization sequence.
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