Fluorinated piperidine iminosugars and their N -alkylated derivatives: Synthesis, conformational analysis, immunosuppressive and glycosidase inhibitory activity studies

Bhuma, Naresh; Burade, Sachin S.; Louat, Thierry; Herman, Jean; Kawade, Sonali; Doshi, Pooja; Dhavale, Dilip D.

doi:10.1016/j.tet.2017.12.059

Cited by 9 publications

(7 citation statements)

References 41 publications

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“…[23] Further detailed computations and experimental observations of additional fluorinated piperidine derivatives can be found in the literature. [77,81] Theoretical studies on the conformational behavior of 2-fluoropiperidines have been conducted as well (Figure 12 A). [82,83] There are four possible conformers for 2-fluoropiperidine 64, where the axial-equatorial conformer (64 ax,eq ) is calculated to be the lowest energy conformer in both gas phase and DMSO.…”

Section: Fluorine Orientation In Five-membered Ringsmentioning

confidence: 99%

Fluorinated Rings: Conformation and Application

Mondal

Agbaria

Nairoukh

2021

Chemistry A European J

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The introduction of fluorine atoms into molecules and materials across many fields of academic and industrial research is now commonplace, owing to their unique properties. A particularly interesting feature is the impact of fluorine substitution on the relative orientation of a C−F bond when incorporated into organic molecules. In this Review, we will be discussing the conformational behavior of fluorinated aliphatic carbo‐ and heterocyclic systems. The conformational preference of each system is associated with various interactions introduced by fluorine substitution such as charge‐dipole, dipole‐dipole, and hyperconjugative interactions. The contribution of each interaction on the stabilization of the fluorinated alicyclic system, which manifests itself in low conformations, will be discussed in detail. The novelty of this feature will be demonstrated by presenting the most recent applications.

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Section: Fluorine Orientation In Five-membered Ringsmentioning

confidence: 99%

Fluorinated Rings: Conformation and Application

Mondal

Agbaria

Nairoukh

2021

Chemistry A European J

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“…Among the variety of aromatic and saturated structures, the piperidine ring has a special role, as it is the most widely occurring form of nitrogen in FDA-approved drugs [ 3 ]. The ability of fluorine atoms to modify basicity, lipophilicity, as well as the hydrogen-bonding properties of amines [ 4 – 5 ] makes fluorinated piperidines [ 6 – 7 ] attractive targets in medicinal chemistry [ 8 – 9 ]. Previous efforts were mainly focused on the synthesis of mono- and difluorinated compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

Supranovich

Dmitriev

Dilman

2020

Beilstein J. Org. Chem.

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A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N–O bond.

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“…Many different naturally occurring structures are known, exceeded by the number of synthetic derivatives, with manifold different modification patterns concerning the carbohydrate scaffold as well as customized derivatisations for different applications. This substance class has been implicated as potential therapeutic agents [ 6 ], for example, as immunomodulators [ 7 , 8 ], as antibacterial [ 9 , 10 ], antiviral [ 11 , 12 ], anti-cancer [ 13 ], and anti-fungal [ 14 ] agents. In addition, iminoalditol-based glycomimetics have been identified as plant growth inhibitors [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

“…Basically all of these compounds have been shown to be highly selective ligands for β -glucosidases. For example, fluorinated iminoxylitols carrying an N -alkyl group [ 23 ] (Fig. 2 ), such as compound 5 , have been found to exhibit immunosuppressive as well as glycosidase inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of modified 1,5-imino-d-xylitols as ligands for lysosomal β-glucocerebrosidase

et al. 2019

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Modified 1,5-dideoxy-1,5-imino- d -xylitol analogues with different substitution patterns involving position C-1 and/or the ring nitrogen were prepared, which were designed to serve as precursors for the preparation of iminoxylitol-based ligands and tools for the elucidation and modulation of human lysosomal β -glucocerebrosidase. Biological evaluation of the synthesized glycomimetics with a series of glycoside hydrolases revealed that these substitution patterns elicit excellent β -glucosidase selectivities. Graphical abstract Electronic supplementary material The online version of this article (10.1007/s00706-019-02427-1) contains supplementary material, which is available to authorized users.

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Fluorinated piperidine iminosugars and their N -alkylated derivatives: Synthesis, conformational analysis, immunosuppressive and glycosidase inhibitory activity studies

Cited by 9 publications

References 41 publications

Fluorinated Rings: Conformation and Application

Fluorinated Rings: Conformation and Application

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

Synthesis of modified 1,5-imino-d-xylitols as ligands for lysosomal β-glucocerebrosidase

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