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Articles de revues sur le sujet « Iminosugars, multivalency, organic synthesis »

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Auteur : Grafiati
Publié le 10 mars 2023

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1

Wang, Yali, Jian Xiao, Aiguo Meng et Chunyan Liu. « Multivalent Pyrrolidine Iminosugars : Synthesis and Biological Relevance ». Molecules 27, no 17 (24 août 2022) : 5420. http://dx.doi.org/10.3390/molecules27175420.

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Recently, the strategy of multivalency has been widely employed to design glycosidase inhibitors, as glycomimetic clusters often induce marked enzyme inhibition relative to monovalent analogs. Polyhydroxylated pyrrolidines, one of the most studied classes of iminosugars, are an attractive moiety due to their potent and specific inhibition of glycosidases and glycosyltransferases, which are associated with many crucial biological processes. The development of multivalent pyrrolidine derivatives as glycosidase inhibitors has resulted in several promising compounds that stand out. Herein, we comprehensively summarized the different synthetic approaches to the preparation of multivalent pyrrolidine clusters, from total synthesis of divalent iminosugars to complex architectures bearing twelve pyrrolidine motifs. Enzyme inhibitory properties and multivalent effects of these synthesized iminosugars were further discussed, especially for some less studied therapeutically relevant enzymes. We envision that this comprehensive review will help extend the applications of multivalent pyrrolidine iminosugars in future studies.
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2

Zelli, Renaud, Pascal Dumy et Alberto Marra. « Metal-free synthesis of imino-disaccharides and calix-iminosugars by photoinduced radical thiol–ene coupling (TEC) ». Organic & ; Biomolecular Chemistry 18, no 13 (2020) : 2392–97. http://dx.doi.org/10.1039/d0ob00198h.

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Deprotected iminosugar alkenes were subjected to thiol–ene coupling with deprotected sugar thiols to afford new imino-disaccharides. Two thiol–ene couplings converted these alkenes into iminosugar thiols and then multivalent iminosugars.
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3

D'Adamio, G., C. Matassini, C. Parmeggiani, S. Catarzi, A. Morrone, A. Goti, P. Paoli et F. Cardona. « Evidence for a multivalent effect in inhibition of sulfatases involved in lysosomal storage disorders (LSDs) ». RSC Advances 6, no 69 (2016) : 64847–51. http://dx.doi.org/10.1039/c6ra15806d.

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4

Matassini, Camilla, Stefania Mirabella, Andrea Goti, Inmaculada Robina, Antonio J. Moreno-Vargas et Francesca Cardona. « Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar ». Beilstein Journal of Organic Chemistry 11 (16 décembre 2015) : 2631–40. http://dx.doi.org/10.3762/bjoc.11.282.

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The synthesis of new multivalent architectures based on a trihydroxypiperidine α-fucosidase inhibitor is reported herein. Tetravalent and nonavalent dendrimers were obtained by means of the click chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive moiety. A preliminary biological investigation is also reported towards commercially available and human glycosidases.
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Lepage, Mathieu L., Alessandra Meli, Anne Bodlenner, Céline Tarnus, Francesco De Riccardis, Irene Izzo et Philippe Compain. « Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores ». Beilstein Journal of Organic Chemistry 10 (23 juin 2014) : 1406–12. http://dx.doi.org/10.3762/bjoc.10.144.

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Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide–alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding affinity enhancements.
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6

McDonnell, Ciaran, Linda Cronin, Julie L. O'Brie et Paul V. Murphy. « A General Synthesis of Iminosugars ». Journal of Organic Chemistry 69, no 10 (mai 2004) : 3565–68. http://dx.doi.org/10.1021/jo035763u.

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7

Sousa, Cristina, Raquel Mendes, Flora Costa, Vera Duarte, António Fortes et Maria Alves. « Synthesis of Iminosugars from Tetroses ». Current Organic Synthesis 11, no 2 (31 mai 2014) : 182–203. http://dx.doi.org/10.2174/15701794113106660074.

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8

Schneider, Jérémy P., Stefano Tommasone, Paolo Della Sala, Carmine Gaeta, Carmen Talotta, Céline Tarnus, Placido Neri, Anne Bodlenner et Philippe Compain. « Synthesis and Glycosidase Inhibition Properties of Calix[8]arene-Based Iminosugar Click Clusters ». Pharmaceuticals 13, no 11 (5 novembre 2020) : 366. http://dx.doi.org/10.3390/ph13110366.

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A set of 6- to 24-valent clusters was constructed with terminal deoxynojirimycin (DNJ) inhibitory heads through C6 or C9 linkers by way of Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions between mono- or trivalent azido-armed iminosugars and calix[8]arene scaffolds differing in their valency and their rigidity but not in their size. The power of multivalency to upgrade the inhibition potency of the weak DNJ inhibitor (monovalent DNJ Ki being at 322 and 188 µM for C6 or C9 linkers, respectively) was evaluated on the model glycosidase Jack Bean α-mannosidase (JBα-man). Although for the clusters with the shorter C6 linker the rigidity of the scaffold was essential, these parameters had no influence for clusters with C9 chains: all of them showed rather good relative affinity enhancements per inhibitory epitopes between 70 and 160 highlighting the sound combination of the calix[8]arene core and the long alkyl arms. Preliminary docking studies were performed to get insights into the preferred binding modes.
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9

Al Bujuq, Nader, et Manuel Angulo. « Synthesis of N-substituted Five and Six-membered Iminocyclitols-bearing Sugar Moiety : Strategy Toward the Synthesis of Pseudodisaccharide ». Current Organic Synthesis 15, no 6 (29 août 2018) : 853–62. http://dx.doi.org/10.2174/1570179415666180601083944.

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Aim and Objective: The efficient synthesis of disaccharide containing iminosugar moiety has a considerable interest in the field of glycoscience. In the present work, we describe a novel and applicable method for synthesis of five and six-membered N-substituted iminosugars attached with sugar moiety (pseudodisaccharides). Materials and Methods: The method of the glycosylation was based on the coupling of iminosugar thioglycoside (glycosyl donors) with partially protected sugars (glycosyl acceptors) in the presence of DMTST as a promoter. 2D COSY, HMQC, HMBC experiments were carried out to assist in NMR signal assignments. The pseudoanomeric configuration was established through NOE experiments and molecular modeling calculations. Results: Two classes of pseudodisaccharides were successfully obtained, five and six-membered N-substituted iminosugars glycosides. The six-membered pseudodisaccharides compounds were produced selectively with only β anomer. The corresponding five-membered pseudodisaccharides were achieved with moderate stereoselectivity. The yields obtained were good. These derivatives of iminocyclitols are thought to be precedents to develop various pseudodisaccharides, novel biologically active compounds, and new functional molecules. Conclusion: According to the results, utilizing iminosugar thioglycosides (1 and 2) as a glycosyl donor in glycosylation reactions is an efficient and highly stereoselective method to prepare (five- and six-membered) iminocyclitols (iminosugars) that bear a sugar moiety. The results will add to the synthesis of the iminosugars derivatives and contribute to make our approach among the few methods able to synthesize iminosugar glycosides.
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10

Esposito, Anna, Daniele D’Alonzo, Maria De Fenza, Eliana De Gregorio, Anna Tamanini, Giuseppe Lippi, Maria Cristina Dechecchi et Annalisa Guaragna. « Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis ». International Journal of Molecular Sciences 21, no 9 (9 mai 2020) : 3353. http://dx.doi.org/10.3390/ijms21093353.

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Iminosugars are sugar analogues endowed with a high pharmacological potential. The wide range of biological activities exhibited by these glycomimetics associated with their excellent drug profile make them attractive therapeutic candidates for several medical interventions. The ability of iminosugars to act as inhibitors or enhancers of carbohydrate-processing enzymes suggests their potential use as therapeutics for the treatment of cystic fibrosis (CF). Herein we review the most relevant advances in the field, paying attention to both the chemical synthesis of the iminosugars and their biological evaluations, resulting from in vitro and in vivo assays. Starting from the example of the marketed drug NBDNJ (N-butyl deoxynojirimycin), a variety of iminosugars have exhibited the capacity to rescue the trafficking of F508del-CFTR (deletion of F508 residue in the CF transmembrane conductance regulator), either alone or in combination with other correctors. Interesting results have also been obtained when iminosugars were considered as anti-inflammatory agents in CF lung disease. The data herein reported demonstrate that iminosugars hold considerable potential to be applied for both therapeutic purposes.
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11

Aguilar, Matilde, Paula Díaz-Pérez, M. Isabel García-Moreno et José M. García Fernández. « Synthesis and Biological Evaluation of Guanidine-Type Iminosugars ». Journal of Organic Chemistry 73, no 5 (mars 2008) : 1995–98. http://dx.doi.org/10.1021/jo702374f.

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12

Ayad, Tahar, Yves Genisson et Michel Baltas. « Chemical Approaches Towards Synthesis of Some Naturally Occurring Iminosugars ». Current Organic Chemistry 8, no 13 (1 septembre 2004) : 1211–33. http://dx.doi.org/10.2174/1385272043370005.

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13

Mane, Rajendra S., K. S. Ajish Kumar et Dilip D. Dhavale. « Synthesis of γ-Hydroxyalkyl Substituted Piperidine Iminosugars fromd-Glucose ». Journal of Organic Chemistry 73, no 8 (avril 2008) : 3284–87. http://dx.doi.org/10.1021/jo800044r.

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14

Yuan, Wen, Yang Pan, Xiaoke Zhang, Peng Liang, Jichao Zhang, Wei Jiao et Huawu Shao. « Direct and highly stereoselective synthesis of quinolizidine iminosugars promoted by l-proline-Et3N ». Organic & ; Biomolecular Chemistry 16, no 47 (2018) : 9230–36. http://dx.doi.org/10.1039/c8ob01953c.

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15

Więcław, Michał Mateusz, et Bartłomiej Furman. « Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams ». Beilstein Journal of Organic Chemistry 17 (13 janvier 2021) : 115–23. http://dx.doi.org/10.3762/bjoc.17.12.

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Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz’s reagent-mediated reductive amide functionalization followed by a variant of the Ugi–azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title products. Finally, some surprising observations regarding the mechanism of their formation were made.
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16

Malinowski, Maciej, Raphaël Hensienne, Nicolas Kern, Damien Tardieu, Anne Bodlenner, Damien Hazelard et Philippe Compain. « Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars ». Organic & ; Biomolecular Chemistry 16, no 25 (2018) : 4688–700. http://dx.doi.org/10.1039/c8ob01065j.

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17

Stocker, Bridget L., Emma M. Dangerfield, Anna L. Win-Mason, Gregory W. Haslett et Mattie S. M. Timmer. « Recent Developments in the Synthesis of Pyrrolidine-Containing Iminosugars ». European Journal of Organic Chemistry 2010, no 9 (mars 2010) : 1615–37. http://dx.doi.org/10.1002/ejoc.200901320.

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18

Clemente, Francesca, Camilla Matassini et Francesca Cardona. « Reductive Amination Routes in the Synthesis of Piperidine IminoSugars ». European Journal of Organic Chemistry 2020, no 29 (14 avril 2020) : 4447–62. http://dx.doi.org/10.1002/ejoc.201901840.

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19

Stauffert, Fabien, Jenny Serra-Vinardell, Marta Gómez-Grau, Helen Michelakakis, Irene Mavridou, Daniel Grinberg, Lluïsa Vilageliu et al. « Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity ». Organic & ; Biomolecular Chemistry 15, no 17 (2017) : 3681–705. http://dx.doi.org/10.1039/c7ob00443e.

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20

Zhao, Wen-Bo, Shinpei Nakagawa, Atsushi Kato, Isao Adachi, Yue-Mei Jia, Xiang-Guo Hu, George W. J. Fleet et al. « General Synthesis of Sugar-Derived Azepane Nitrones : Precursors of Azepane Iminosugars ». Journal of Organic Chemistry 78, no 7 (11 mars 2013) : 3208–21. http://dx.doi.org/10.1021/jo400130p.

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Paśniczek, Konrad, Dariusz Socha, Margarita Jurczak, Jolanta Solecka et Marek Chmielewski. « Synthesis of 8-homocastanospermine ». Canadian Journal of Chemistry 84, no 4 (1 avril 2006) : 534–39. http://dx.doi.org/10.1139/v06-032.

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The 1,3-dipolar cycloaddition of a five-membered cyclic nitrone derived from malic acid (4) and unsaturated D-threo-hexaldonolactone (1) leads to a single adduct 6, which can be transformed into the 8-homocastanospermine (13) via a sequence involving rearrangement of the six-membered lactone ring into the five-membered one, removal of the terminal carbon atom from the sugar chain, cleavage of the N—O bond, and the intramolecular alkylation of the nitrogen atom. The iminosugar (13) does not show any interesting inhibitory activity towards α- and β-glucosidases.Key words: iminosugars, homocastanospermine, nitrones, aldono-1,5-lactone, 1,3-dipolar cycloaddition, glucosidases.
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22

Jia, Yue-Mei, Chu-Yi Yu, Wu-Bao Wang, Mu-Hua Huang, Yi-Xian Li, Pei-Xin Rui, Xiang-Guo Hu et al. « A Practical Synthesis of Sugar-Derived Cyclic Nitrones : Powerful Synthons for the Synthesis of Iminosugars ». Synlett 2010, no 03 (11 janvier 2010) : 488–92. http://dx.doi.org/10.1055/s-0029-1219189.

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23

Liu, Xu, Lulu Su, Zhaoxi Zhou, Liping Niu, Ligang Gao, Huanhuan Ju, Fengxing Li, Xiaoliu Li et Hua Chen. « Design and Synthesis of Benzimidazole-Iminosugars and Their Inhibitory Activities against Glycosidases ». Chinese Journal of Organic Chemistry 41, no 7 (2021) : 2861. http://dx.doi.org/10.6023/cjoc202101055.

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Zhao, Hui, Wen-Bo Zhao, Jian-She Zhu, Yue-Mei Jia et Chu-Yi Yu. « An Efficient Synthesis of Aldohexose-Derived Piperidine Nitrones : Precursors of Piperidine Iminosugars ». Molecules 18, no 5 (21 mai 2013) : 6021–34. http://dx.doi.org/10.3390/molecules18056021.

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Behr, Jean-Bernard, Adel Kalla, Dominique Harakat et Richard Plantier-Royon. « Tandem Nucleophilic Addition/Cyclization Reaction in the Synthesis of Ketimine-Type Iminosugars ». Journal of Organic Chemistry 73, no 9 (mai 2008) : 3612–15. http://dx.doi.org/10.1021/jo702616x.

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Prasad, Sure Siva, Soundararasu Senthilkumar, Akriti Srivastava et Sundarababu Baskaran. « Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars ». Organic Letters 19, no 16 (7 août 2017) : 4403–6. http://dx.doi.org/10.1021/acs.orglett.7b02175.

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Luo, Hairong, Wei Zou et Huawu Shao. « Synthesis of N-substituted iminosugars from 2′-carbonyl-C-glycofuranosides ». Carbohydrate Research 344, no 18 (décembre 2009) : 2454–60. http://dx.doi.org/10.1016/j.carres.2009.08.024.

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Xie, Juan, Tatyana Güveli, Séverine Hebbe et Luc Dechoux. « Synthesis of novel 1-N-iminosugars from chiral nonracemic bicyclic lactams ». Tetrahedron Letters 45, no 25 (juin 2004) : 4903–6. http://dx.doi.org/10.1016/j.tetlet.2004.04.121.

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Moriyama, Noriaki, Yoshihiro Matsumura, Masami Kuriyama et Osamu Onomura. « Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine ». Tetrahedron : Asymmetry 20, no 23 (décembre 2009) : 2677–87. http://dx.doi.org/10.1016/j.tetasy.2009.11.028.

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Veselov, Ivan S., Alexandr M. Petrenko, Dmitriy M. Mazur et Galina V. Grishina. « Regio - and stereoselective synthesis of the iminosugars – 4-substituted 1-benzylpiperidine-3,5-diols ». Arkivoc 2019, no 5 (13 février 2019) : 50–59. http://dx.doi.org/10.24820/ark.5550190.p010.713.

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Prasad, Sure Siva, et Sundarababu Baskaran. « Iminosugar C-Nitromethyl Glycoside : Stereoselective Synthesis of Isoxazoline and Isoxazole-Fused Bicyclic Iminosugars ». Journal of Organic Chemistry 83, no 3 (24 janvier 2018) : 1558–64. http://dx.doi.org/10.1021/acs.joc.7b02803.

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Cren, Sylvaine, Claire Wilson et Neil R. Thomas. « A Rapid Synthesis of Hexofuranose-like Iminosugars Using Ring-Closing Metathesis ». Organic Letters 7, no 16 (août 2005) : 3521–23. http://dx.doi.org/10.1021/ol051232b.

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Guaragna, Annalisa, Stefano D'Errico, Daniele D'Alonzo, Silvana Pedatella et Giovanni Palumbo. « A General Approach to the Synthesis of 1-Deoxy-l-iminosugars ». Organic Letters 9, no 17 (août 2007) : 3473–76. http://dx.doi.org/10.1021/ol7014847.

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Luo, Bo, Filipa Marcelo, Jérôme Désiré, Yongmin Zhang, Matthieu Sollogoub, Atsushi Kato, Isao Adachi, F. Javier Cañada, Jesús Jiménez-Barbero et Yves Blériot. « Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars ». Journal of Carbohydrate Chemistry 30, no 7-9 (1 septembre 2011) : 641–54. http://dx.doi.org/10.1080/07328303.2011.630547.

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35

Santana, Andrés G., Nieves R. Paz, Cosme G. Francisco, Ernesto Suárez et Concepción C. González. « Synthesis of Branched Iminosugars through a Hypervalent Iodine(III)-Mediated Radical-Polar Crossover Reaction ». Journal of Organic Chemistry 78, no 15 (25 juillet 2013) : 7527–43. http://dx.doi.org/10.1021/jo401041s.

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Wennekes, Tom, Richard J. B. H. N. van den Berg, Kimberly M. Bonger, Wilma E. Donker-Koopman, Amar Ghisaidoobe, Gijsbert A. van der Marel, Anneke Strijland, Johannes M. F. G. Aerts et Herman S. Overkleeft. « Synthesis and evaluation of dimeric lipophilic iminosugars as inhibitors of glucosylceramide metabolism ». Tetrahedron : Asymmetry 20, no 6-8 (mai 2009) : 836–46. http://dx.doi.org/10.1016/j.tetasy.2009.02.043.

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Puet, Alejandro, Gema Domínguez, Francisco Javier Cañada et Javier Pérez-Castells. « Synthesis and Evaluation of Novel Iminosugars Prepared from Natural Amino Acids ». Molecules 26, no 2 (13 janvier 2021) : 394. http://dx.doi.org/10.3390/molecules26020394.

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Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural amino acids l-serine and l-alanine. Those prepared from the latter amino acid may mimic l-fucose, a natural-occurring monosaccharide involved in many molecular recognition events. Final compounds prepared from l-serine bear S configurations on the C5 position. The synthesis involved a stereoselective cyclopropanation reaction of an α,β-unsaturated piperidone, which was prepared through a ring-closing metathesis. The final compounds were tested as possible inhibitors of different glycosidases. The results, although, in general, with low inhibition activity, showed selectivity, depending on the compound and enzyme, and in some cases, an unexpected activity enhancement was observed.
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Martínez-Bailén, Macarena, Ana T. Carmona, Francesca Cardona, Camilla Matassini, Andrea Goti, Moemi Kubo, Atsushi Kato, Inmaculada Robina et Antonio J. Moreno-Vargas. « Synthesis of multimeric pyrrolidine iminosugar inhibitors of human β-glucocerebrosidase and α-galactosidase A : First example of a multivalent enzyme activity enhancer for Fabry disease ». European Journal of Medicinal Chemistry 192 (avril 2020) : 112173. http://dx.doi.org/10.1016/j.ejmech.2020.112173.

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Sun, Jiajing, Yaqing Kang, Ligang Gao, Xin Lu, Huanhuan Ju, Xiaoliu Li et Hua Chen. « Synthesis of tricyclic quinazolinone-iminosugars as potential glycosidase inhibitors via a Mitsunobu reaction ». Carbohydrate Research 478 (mai 2019) : 10–17. http://dx.doi.org/10.1016/j.carres.2019.04.002.

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Yan, Lianhai, Hui Lui, Jiajing Sun, Ligang Gao, Xin Lu, Xiaoliu Li et Hua Chen. « Synthesis of tricyclic benzimidazole-iminosugars as potential glycosidase inhibitors via a Mitsunobu reaction ». Carbohydrate Research 485 (novembre 2019) : 107807. http://dx.doi.org/10.1016/j.carres.2019.107807.

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Cipolla, Laura, Marcos Reis Fernandes, Maria Gregori, Cristina Airoldi et Francesco Nicotra. « Synthesis and biological evaluation of a small library of nojirimycin-derived bicyclic iminosugars ». Carbohydrate Research 342, no 12-13 (septembre 2007) : 1813–30. http://dx.doi.org/10.1016/j.carres.2007.04.002.

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Wibowo, Agustono, Zurina Shaameri, Mohd Fazli Mohammat et Ahmad Sazali Hamzah. « A multi-component reaction approach to the synthesis of potent antidiabetic agents five-membered iminosugars analogues ». Organic Communications 13, no 3 (27 septembre 2020) : 79–88. http://dx.doi.org/10.25135/acg.oc.85.20.08.1765.

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Cocaud, Chloé, Cyril Nicolas, Thomas Poisson, Xavier Pannecoucke, Claude Y. Legault et Olivier R. Martin. « Tunable Approach for the Stereoselective Synthesis of 1-C-Diethylphosphono(difluoromethyl) Iminosugars as Glycosyl Phosphate Mimics ». Journal of Organic Chemistry 82, no 5 (21 février 2017) : 2753–63. http://dx.doi.org/10.1021/acs.joc.6b03071.

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Guanti, Giuseppe, et Renata Riva. « Asymmetrized tris(hydroxymethyl)methane as precursor of iminosugars : application to the synthesis of isofagomine ». Tetrahedron Letters 44, no 2 (janvier 2003) : 357–60. http://dx.doi.org/10.1016/s0040-4039(02)02492-9.

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De Angelis, Martina, Carla Sappino, Emanuela Mandic, Marianna D’Alessio, Maria Grazia De Dominicis, Sara Sannino, Ludovica Primitivo, Paolo Mencarelli, Alessandra Ricelli et Giuliana Righi. « Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin ». Tetrahedron 79 (janvier 2021) : 131837. http://dx.doi.org/10.1016/j.tet.2020.131837.

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46

Wang, Haibo, Senling Tang, Guoqing Zhang, Yang Pan, Wei Jiao et Huawu Shao. « Synthesis of N-Substituted Iminosugar C-Glycosides and Evaluation as Promising α-Glucosidase Inhibitors ». Molecules 27, no 17 (27 août 2022) : 5517. http://dx.doi.org/10.3390/molecules27175517.

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A series of N-substituted iminosugar C-glycosides were synthesized and tested for α-glucosidase inhibition. The results suggested that 6e is a promising and potent α-glucosidase inhibitor. Enzymatic kinetic assays indicated that compound 6e may be classified as an uncompetitive inhibitor. The study of structure-activity relationships of those iminosugars provided a starting point for the discovery of new α-glucosidase inhibitors.
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Szcześniak, Piotr, Barbara Grzeszczyk et Bartłomiej Furman. « A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams ». Molecules 26, no 18 (8 septembre 2021) : 5459. http://dx.doi.org/10.3390/molecules26185459.

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An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz’s reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel’s or diffusion control models, which affords amino-modified iminosugars, such as ADMDP or higher nojirimycin derivatives.
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Liu, Hai-Qian, Cheng-Cheng Song, You-Hong Niu, Tao Li, Qin Li et Xin-Shan Ye. « Synthesis and biological evaluation of N-arylated-lactam-type iminosugars as potential immunosuppressive agents ». Organic & ; Biomolecular Chemistry 15, no 28 (2017) : 5912–19. http://dx.doi.org/10.1039/c7ob01110e.

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Qian, Bao-Chen, Akiko Kamori, Kyoko Kinami, Atsushi Kato, Yi-Xian Li, George W. J. Fleet et Chu-Yi Yu. « Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars ». Org. Biomol. Chem. 14, no 19 (2016) : 4488–98. http://dx.doi.org/10.1039/c6ob00531d.

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Gautier-Lefebvre, Isabelle, Jean-Bernard Behr, Georges Guillerm et Murielle Muzard. « Iminosugars as glycosyltransferase inhibitors : synthesis of polyhydroxypyrrolidines and their evaluation on chitin synthase activity ». European Journal of Medicinal Chemistry 40, no 12 (décembre 2005) : 1255–61. http://dx.doi.org/10.1016/j.ejmech.2005.07.001.

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