4.6 Review

Multivalent Pyrrolidine Iminosugars: Synthesis and Biological Relevance

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Green Chemistry in the Synthesis of Pharmaceuticals

Supratik Kar et al.

Summary: The principles of green chemistry can be effectively implemented in the green synthesis of pharmaceuticals by choosing solvent-free or green solvents, considering one-pot synthesis, multicomponent reactions, continuous processing, and process intensification approaches. Researchers and industries are actively pursuing green synthesis processes to control waste reduction and protect the environment.

CHEMICAL REVIEWS (2022)

Article Biochemistry & Molecular Biology

Discovery of human hexosaminidase inhibitors by in situ screening of a library of mono- and divalent pyrrolidine iminosugars

Valeria Pingitore et al.

Summary: Two libraries of mono- and dimeric pyrrolidine iminosugars were synthesized and screened for inhibition of enzymes from Jack beans and human lysosomal hexosaminidases, resulting in the identification of potent and selective inhibitors for human nucleocytoplasmic beta-N-acetylglucosaminidase.

BIOORGANIC CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

The Synthesis and Glycoside Formation of Polyfluorinated Carbohydrates

Kler Huonnic et al.

Summary: This article reviews the research progress on polyfluorinated carbohydrates, including the synthesis of polyfluorinated hexoses, pentoses, ketosugars, and aminosugars (including sialic acids and nucleosides), and provides an overview of the state-of-the-art glycosidation techniques.

CHEMICAL REVIEWS (2022)

Article Chemistry, Medicinal

Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives

Jun-Zhe Wang et al.

Summary: This study designed and synthesized two series of C-4 alkylated and arylated LAB and DAB derivatives, and evaluated their activity against various glycosidases. The results revealed potential inhibitory effects of some derivatives and provided guidance for drug design and development.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

Article Chemistry, Medicinal

Recent results from non-basic glycosidase inhibitors: How structural diversity can inform general strategies for improving inhibition potency

Michela Simone et al.

Summary: This review summarizes the literature on glycosidase inhibitors without a basic nitrogen in the past 15 years, focusing on natural terpenoids and mono- and polycyclic aromatic hydrocarbons. From diverse structures, insights into inhibitor structural features applicable to the optimization of all glycosidase inhibitors, including iminosugars, are identified.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

Article Biochemistry & Molecular Biology

Design and synthesis of novel benzimidazole-iminosugars linked a substituted phenyl group and their inhibitory activities against β-glucosidase

Xu Liu et al.

Summary: A series of novel benzimidazole-iminosugars compounds were designed and synthesized, and their inhibitory activities against beta-glucosidase were evaluated. Some of the compounds showed significant inhibitory activities, and the additional phenyl ring and electron donating groups were found to be beneficial for the activity. The binding modes of these compounds to beta-glucosidase were found to be different. Molecular docking studies also suggested that the additional phenyl ring played an important role in the inhibitory activity.

BIOORGANIC CHEMISTRY (2022)

Article Chemistry, Medicinal

Multivalent glucosidase inhibitors based on perylene bisimide and iminosugar conjugates

Jian-Xing Yang et al.

Summary: In this study, compounds with different numbers of DNJ moieties were synthesized, and it was found that PBI-6DNJ showed stronger hypoglycemic effects. Additionally, PBI-6DNJ demonstrated consistent results in both in vivo and in vitro experiments, providing a basic understanding for evaluating hypoglycemic potency and designing multivalent glucosidase inhibitors.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

Review Biochemistry & Molecular Biology

1-Deoxnojirinicin and its Derivatives: A Mini Review of the Literature

Haijun Wang et al.

Summary: Deoxynojirimycin (1-DNJ) is a natural sugar analogue with unique bioactivities, found in mulberry leaves, silkworms, and certain microorganisms. It is a potent alpha-glucosidase inhibitor with anti-hyperglycemic, anti-obese, anti-viral, and anti-tumor properties. Derivatives of 1-DNJ like miglitol, miglustat, and migalastat have clinical applications in treating diseases such as diabetes and lysosomal storage disorders.

CURRENT MEDICINAL CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Approaches to the Synthesis of Perfluoroalkyl-Modified Carbohydrates and Derivatives: Thiosugars, Iminosugars, and Tetrahydro(thio)pyrans

Maria Laura Uhrig et al.

Summary: Fluoroalkyl-substituted carbohydrates play important roles in wetting, antifreeze, and coating agents, and are significant to the synthetic carbohydrate community. This study summarizes the methods for installing R-F groups onto carbohydrates and derivatives, as well as presents new advances in the synthesis of fluoroalkyl-substituted iminosugars.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Multidisciplinary

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Debashis Dhara et al.

Summary: This personal account focuses on the synthesis of polyhydroxylated piperidines, a subset of compounds within the iminosugar family, using various cyclisation methods and enantiomerically pure precursors to obtain substituted piperidines. The laboratory has contributed cascades based on reductive amination and Huisgen azide-alkene cycloaddition for the synthesis of substituted piperidines with quaternary centres adjacent to nitrogen.

CHEMICAL RECORD (2021)

Article Biochemistry & Molecular Biology

Hybrid Multivalent Jack Bean α-Mannosidase Inhibitors: The First Example of Gold Nanoparticles Decorated with Deoxynojirimycin Inhitopes

Costanza Vanni et al.

Summary: In this study, water dispersible gold nanoparticles coated with iminosugar deoxynojirimycin (DNJ) and simple monosaccharides were prepared, leading to enhanced inhibitory activity towards Jack bean alpha-mannosidase. A novel strategy involving longer amphiphilic linker and trimeric presentation of the inhitope was employed, resulting in a significant increase in inhibitory potency.

MOLECULES (2021)

Article Chemistry, Medicinal

Positional Isomeric Effects on the Optical Properties, Multivalent Glycosidase Inhibition Effect, and Hypoglycemic Effect of Perylene Bisimide-deoxynojirimycin Conjugates

Ren-Feng Li et al.

Summary: The paper synthesized two positional isomeric perylene bisimide derivatives and studied their performance in glycosidase inhibition and hypoglycemic effects. PBI-4DNJ-1 exhibited potent hypoglycemic effects in mice, with the highest binding and hydrogen bond energy related to the isomeric effect on hypoglycemic activity. This work introduced a new approach to develop antihyperglycemic agents in the field of multivalent glycomimetics.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Biochemistry & Molecular Biology

An overview of therapeutic potential of N-alkylated 1-deoxynojirimycin congeners

Mehwish Iftikhar et al.

Summary: Polyhydroxylated alkaloids, with 1-deoxynojirimycin as a popular representative, demonstrate diverse biological activities and potential therapeutic applications. Congeners of 1-deoxynojirimycin have shown inhibitory effects on various enzymes, suggesting their future utility as inspirations for further studies.

CARBOHYDRATE RESEARCH (2021)

Article Chemistry, Organic

Multivalent resorcinarene clusters decorated with DAB-1 inhitopes: targeting Golgi α-mannosidase from Drosophila melanogaster

Paolo Della Sala et al.

Summary: The synthesis of multivalent ligands anchored to resorcinarene scaffolds showed significant multivalent effects towards GMIIb, a recombinant Drosophila homolog of over-expressed human Golgi alpha-mannosidase II, indicating promising inhibitory potency. Computational studies helped to understand the origin of the multivalent effect and the relative inhibitory potency of the new architectures.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Organic

Iminosugars as glycosyltransferase inhibitors

Irene Conforti et al.

Summary: Iminosugars, natural carbohydrate analogues, have been explored for developing new drugs to treat diseases by inhibiting enzyme activity, and their inhibition of specific glycosyltransferases could lead to innovative therapeutic agents.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Multivalent Effect in Glycosidase Inhibition: The End of the Beginning

Philippe Compain

CHEMICAL RECORD (2020)

Article Chemistry, Multidisciplinary

Imino- and Azasugar Protonation Inside Human Acid β-Glucosidase, the Enzyme that is Defective in Gaucher Disease

Camilla Matassini et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Pharmacology & Pharmacy

Iminosugars: A host-targeted approach to combat Flaviviridae infections

Lisa Evans DeWald et al.

ANTIVIRAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Carbohydrate supramolecular chemistry: beyond the multivalent effect

Manuel Gonzalez-Cuesta et al.

CHEMICAL COMMUNICATIONS (2020)

Article Biochemistry & Molecular Biology

Exploring substituent diversity on pyrrolidine-aryltriazole iminosugars: Structural basis of β-glucocerebrosidase inhibition

Macarena Martinez-Bailen et al.

BIOORGANIC CHEMISTRY (2019)

Article Biochemistry & Molecular Biology

Dual targeting of PTP1B and glucosidases with new bifunctional iminosugar inhibitors to address type 2 diabetes

Xhenti Ferhati et al.

BIOORGANIC CHEMISTRY (2019)

Article Biochemistry & Molecular Biology

Structural basis of the inhibition of GH1 β-glucosidases by multivalent pyrrolidine iminosugars

Macarena Martinez-Bailen et al.

BIOORGANIC CHEMISTRY (2019)

Article Chemistry, Medicinal

Iminosugars: Effects of Stereochemistry, Ring Size, and N-Substituents on Glucosidase Activities

Luis O. B. Zamoner et al.

PHARMACEUTICALS (2019)

Article Chemistry, Multidisciplinary

Structural Basis of Outstanding Multivalent Effects in Jack Bean -Mannosidase Inhibition

Eduardo Howard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Biochemistry & Molecular Biology

Biological activities of 3,4,5-trihydroxypiperidines and their N- and O-derivatives

Kate Prichard et al.

CHEMICAL BIOLOGY & DRUG DESIGN (2018)

Article Chemistry, Medicinal

Harnessing pyrrolidine iminosugars into dimeric structures for the rapid discovery of divalent glycosidase inhibitors

Ana T. Carmona et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2018)

Review Biochemistry & Molecular Biology

Biological functions of fucose in mammals

Michael Schneider et al.

GLYCOBIOLOGY (2017)

Article Chemistry, Multidisciplinary

Mechanistic Insight into the Binding of Multivalent Pyrrolidines to α-Mannosidases

Stefania Mirabella et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Biochemistry & Molecular Biology

Design, synthesis and bioactivity evaluation of Galf mimics as antitubercular agents

Chunyan Liu et al.

CARBOHYDRATE RESEARCH (2016)

Article Chemistry, Multidisciplinary

Iminosugar-Cyclopeptoid Conjugates Raise Multivalent Effect in Glycosidase Inhibition at Unprecedented High Levels

Mathieu L. Lepage et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Multidisciplinary

Solid-state assembly of a resorcin[6]arene in twin molecular capsules

Giovanna Brancatelli et al.

CRYSTENGCOMM (2016)

Article Chemistry, Organic

Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

Yi-Xian Li et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Organic

Cycloadditions of Sugar-Derived Nitrones Targeting Polyhydroxylated Indolizidines

Daniele Martella et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Organic

Improved Synthesis of Larger Resorcinarenes

Paolo Della Sala et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Organic

Expanding the library of divalent fucosidase inhibitors with polyamino and triazole-benzyl bridged bispyrrolidines

Audrey Hottin et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Article Chemistry, Organic

Exploring the divalent effect in fucosidase inhibition with stereoisomeric pyrrolidine dimers

Audrey Hottin et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Article Chemistry, Organic

A tetrasulfate-resorcin[6]arene cavitand as the host for organic ammonium guests

Carmine Gaeta et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

Article Chemistry, Multidisciplinary

A Convenient Approach to Stereoisomeric Iminocyclitols: Generation of Potent Brain-Permeable OGA Inhibitors

Milan Bergeron-Brlek et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Oncology

Anti-cancer Glycosidase Inhibitors from Natural Products: A Computational and Molecular Modelling Perspective

Ashona Singh et al.

ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY (2015)

Article Biochemical Research Methods

Polymeric Iminosugars Improve the Activity of Carbohydrate-Processing Enzymes

Yoan Brissonnet et al.

BIOCONJUGATE CHEMISTRY (2015)

Article Biochemistry & Molecular Biology

Exploiting the Hydrophobic Terrain in Fucosidases with Aryl-Substituted Pyrrolidine Iminosugars

Audrey Hottin et al.

CHEMBIOCHEM (2015)

Article Biochemistry & Molecular Biology

N-Bridged 1-deoxynojirimycin dimers as selective insect trehalase inhibitors

Laura Cipolla et al.

CARBOHYDRATE RESEARCH (2014)

Review Biochemistry & Molecular Biology

The Multivalent Effect in Glycosidase Inhibition: A New, Rapidly Emerging Topic in Glycoscience

Philippe Compain et al.

CHEMBIOCHEM (2014)

Review Chemistry, Multidisciplinary

Multivalent Inhibitors for Carbohydrate-Processing Enzymes: Beyond the Lock-and-Key Concept

Sebastien G. Gouin

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Article Pharmacology & Pharmacy

Elosulfase alfa: First Global Approval

Mark Sanford et al.

DRUGS (2014)

Article Biochemistry & Molecular Biology

Jack bean α-mannosidase: Amino acid sequencing and N-glycosylation analysis of a valuable glycomics tool

B. S. Gnanesh Kumar et al.

GLYCOBIOLOGY (2014)

Review Multidisciplinary Sciences

Sphingolipid lysosomal storage disorders

Frances M. Platt

NATURE (2014)

Article Chemistry, Organic

Rapid discovery of potent α-fucosidase inhibitors by in situ screening of a library of (pyrrolidin-2-yl)triazoles

Pilar Elias-Rodriguez et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

Article Chemistry, Organic

Total synthesis of AI-77-B

Maddimsetti Venkateswara Rao et al.

TETRAHEDRON LETTERS (2014)

Review Chemistry, Multidisciplinary

Bridging lectin binding sites by multivalent carbohydrates

Valentin Wittmann et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Organic

Exploring a Multivalent Approach to α-L-Fucosidase Inhibition

Elena Moreno-Clavijo et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

Article Endocrinology & Metabolism

Spinal involvement in mucopolysaccharidosis IVA (Morquio-Brailsford or Morquio A syndrome): presentation, diagnosis and management

Guirish A. Solanki et al.

JOURNAL OF INHERITED METABOLIC DISEASE (2013)

Article Chemistry, Multidisciplinary

Topological Effects and Binding Modes Operating with Multivalent Iminosugar-Based Glycoclusters and Mannosidases

Yoan Brissonnet et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

Towards the Simplification of Protein Synthesis: Iterative Solid-Supported Ligations with Concomitant Purifications

Vincent Aucagne et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Editorial Material Chemistry, Medicinal

A Prospect for Pyrrolidine Iminosugars as Antidiabetic α-Glucosidase Inhibitors

Ana Trapero et al.

JOURNAL OF MEDICINAL CHEMISTRY (2012)

Article Chemistry, Organic

Iminosugar-ferrocene conjugates as potential anticancer agents

Audrey Hottin et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Combining Glycomimetic and Multivalent Strategies toward Designing Potent Bacterial Lectin Inhibitors

Yoann M. Chabre et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

Review Pharmacology & Pharmacy

Iminosugars past, present and future: medicines for tomorrow

Graeme Home et al.

DRUG DISCOVERY TODAY (2011)

Review Chemistry, Medicinal

Iminosugars as therapeutic agents: recent advances and promising trends

Robert J. Nash et al.

FUTURE MEDICINAL CHEMISTRY (2011)

Article Chemistry, Organic

Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine

Alexis Kotland et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Medicinal

Synthetic N-Alkylated Iminosugars as New Potential Immunosuppressive Agents

Guan-Nan Wang et al.

ACS MEDICINAL CHEMISTRY LETTERS (2011)

Article Biochemistry & Molecular Biology

Synthesis and inhibitory activities of novel C-3 substituted azafagomines: A new type of selective inhibitors of α-L-fucosidases

Elena Moreno-Clavijo et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2010)

Review Chemistry, Organic

Recent Developments in the Synthesis of Pyrrolidine-Containing Iminosugars

Bridget L. Stocker et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2010)

Article Chemistry, Organic

Enantioselective Synthesis of (+)-alpha-Conhydrine and (-)-Sedamine by L-Proline-Catalysed alpha-Aminooxylation

Tanveer Mahamadali Shaikh et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2010)

Article Chemistry, Multidisciplinary

Strain-Promoted Alkyne Azide Cycloaddition for the Functionalization of Poly(amide)-Based Dendrons and Dendrimers

Catia Ornelas et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Controlling the Chair Conformation of a Mannopyranose in a Large-Amplitude [2]Rotaxane Molecular Machine

Frederic Coutrot et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

Article Chemistry, Organic

Synthesis of Pentahydroxylated Pyrrolizidines and Indolizidines

Juan A. Tamayo et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

Article Chemistry, Organic

Multivalent iminosugars to modulate affinity and selectivity for glycosidases

Jennifer Diot et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2009)

Article Chemistry, Organic

Synthesis of novel pyrrolidine 3,4-diol derivatives as inhibitors of alpha-L-fucosidases

Elena Moreno-Clavijo et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2009)

Article Multidisciplinary Sciences

Role for α-L-fucosidase in the control of Helicobacter pylori-infected gastric cancer cells

Ta-Wei Liu et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2009)

Article Chemistry, Inorganic & Nuclear

Synthesis and evaluation of dimeric lipophilic iminosugars as inhibitors of glucosylceramide metabolism

Tom Wennekes et al.

TETRAHEDRON-ASYMMETRY (2009)

Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

En-Lun Tsou et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2008)

Article Chemistry, Organic

Expeditive synthesis of glycodendrimer scaffolds based on versatile TRIS and mannoside derivatives

Yoann M. Chabre et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

Article Chemistry, Organic

Hexafluoroisopropanol as a unique solvent for stereoselective lododesilylation of vinylsilanes

Elizabeth A. Ilardi et al.

ORGANIC LETTERS (2008)

Article Chemistry, Organic

A convergent approach for the total synthesis of (-)-synrotolide diacetate

P. Srihari et al.

TETRAHEDRON LETTERS (2007)

Article Chemistry, Organic

Synthesis and conformational analysis of novel trimeric maleimide cross-linking reagents

Agnieszka Szczepanska et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Article Chemistry, Organic

Enantiospecific synthesis of (-)-radicamine B

Chunyan Liu et al.

LETTERS IN ORGANIC CHEMISTRY (2007)

Article Chemistry, Medicinal

Synthetic iminosugar derivatives as new potential immunosuppressive agents

XS Ye et al.

JOURNAL OF MEDICINAL CHEMISTRY (2005)

Article Chemistry, Multidisciplinary

Influencing receptor-ligand binding mechanisms with multivalent ligand architecture

JE Gestwicki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Biochemistry & Molecular Biology

Hexosaminidase inhibitors as new drug candidates for the therapy of osteoarthritis

JJ Liu et al.

CHEMISTRY & BIOLOGY (2001)

Review Biochemistry & Molecular Biology

Synthetic multivalent ligands in the exploration of cell-surface interactions

LL Kiessling et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2000)

Article Biochemistry & Molecular Biology

Mammalian Notch1 is modified with two unusual forms of O-linked glycosylation found on epidermal growth factor-like modules

DJ Moloney et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2000)