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Journal articles on the topic 'Iminosugars, multivalency, organic synthesis'

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Author: Grafiati

Published: 10 March 2023

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1

Wang, Yali, Jian Xiao, Aiguo Meng, and Chunyan Liu. "Multivalent Pyrrolidine Iminosugars: Synthesis and Biological Relevance." Molecules 27, no. 17 (August 24, 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, and 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, and 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, and Francesca Cardona. "Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar." Beilstein Journal of Organic Chemistry 11 (December 16, 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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5

Lepage, Mathieu L., Alessandra Meli, Anne Bodlenner, Céline Tarnus, Francesco De Riccardis, Irene Izzo, and Philippe Compain. "Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores." Beilstein Journal of Organic Chemistry 10 (June 23, 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, and Paul V. Murphy. "A General Synthesis of Iminosugars." Journal of Organic Chemistry 69, no. 10 (May 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, and Maria Alves. "Synthesis of Iminosugars from Tetroses." Current Organic Synthesis 11, no. 2 (May 31, 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, and Philippe Compain. "Synthesis and Glycosidase Inhibition Properties of Calix[8]arene-Based Iminosugar Click Clusters." Pharmaceuticals 13, no. 11 (November 5, 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, and 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 (August 29, 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, and Annalisa Guaragna. "Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis." International Journal of Molecular Sciences 21, no. 9 (May 9, 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, and José M. García Fernández. "Synthesis and Biological Evaluation of Guanidine-Type Iminosugars." Journal of Organic Chemistry 73, no. 5 (March 2008): 1995–98. http://dx.doi.org/10.1021/jo702374f.

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12

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

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13

Mane, Rajendra S., K. S. Ajish Kumar, and Dilip D. Dhavale. "Synthesis of γ-Hydroxyalkyl Substituted Piperidine Iminosugars fromd-Glucose." Journal of Organic Chemistry 73, no. 8 (April 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, and 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, and Bartłomiej Furman. "Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams." Beilstein Journal of Organic Chemistry 17 (January 13, 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, and 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, and Mattie S. M. Timmer. "Recent Developments in the Synthesis of Pyrrolidine-Containing Iminosugars." European Journal of Organic Chemistry 2010, no. 9 (March 2010): 1615–37. http://dx.doi.org/10.1002/ejoc.200901320.

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18

Clemente, Francesca, Camilla Matassini, and Francesca Cardona. "Reductive Amination Routes in the Synthesis of Piperidine IminoSugars." European Journal of Organic Chemistry 2020, no. 29 (April 14, 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 (March 11, 2013): 3208–21. http://dx.doi.org/10.1021/jo400130p.

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21

Paśniczek, Konrad, Dariusz Socha, Margarita Jurczak, Jolanta Solecka, and Marek Chmielewski. "Synthesis of 8-homocastanospermine." Canadian Journal of Chemistry 84, no. 4 (April 1, 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 NO 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 (January 11, 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, and 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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24

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

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25

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

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26

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

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27

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

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28

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

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29

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

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30

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

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31

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

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32

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

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33

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

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34

Luo, Bo, Filipa Marcelo, Jérôme Désiré, Yongmin Zhang, Matthieu Sollogoub, Atsushi Kato, Isao Adachi, F. Javier Cañada, Jesús Jiménez-Barbero, and Yves Blériot. "Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars." Journal of Carbohydrate Chemistry 30, no. 7-9 (September 1, 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, and Concepción C. González. "Synthesis of Branched Iminosugars through a Hypervalent Iodine(III)-Mediated Radical-Polar Crossover Reaction." Journal of Organic Chemistry 78, no. 15 (July 25, 2013): 7527–43. http://dx.doi.org/10.1021/jo401041s.

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36

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, and Herman S. Overkleeft. "Synthesis and evaluation of dimeric lipophilic iminosugars as inhibitors of glucosylceramide metabolism." Tetrahedron: Asymmetry 20, no. 6-8 (May 2009): 836–46. http://dx.doi.org/10.1016/j.tetasy.2009.02.043.

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37

Puet, Alejandro, Gema Domínguez, Francisco Javier Cañada, and Javier Pérez-Castells. "Synthesis and Evaluation of Novel Iminosugars Prepared from Natural Amino Acids." Molecules 26, no. 2 (January 13, 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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38

Martínez-Bailén, Macarena, Ana T. Carmona, Francesca Cardona, Camilla Matassini, Andrea Goti, Moemi Kubo, Atsushi Kato, Inmaculada Robina, and 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 (April 2020): 112173. http://dx.doi.org/10.1016/j.ejmech.2020.112173.

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39

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

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40

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

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41

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

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42

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

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43

Cocaud, Chloé, Cyril Nicolas, Thomas Poisson, Xavier Pannecoucke, Claude Y. Legault, and 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 (February 21, 2017): 2753–63. http://dx.doi.org/10.1021/acs.joc.6b03071.

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44

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

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45

De Angelis, Martina, Carla Sappino, Emanuela Mandic, Marianna D’Alessio, Maria Grazia De Dominicis, Sara Sannino, Ludovica Primitivo, Paolo Mencarelli, Alessandra Ricelli, and Giuliana Righi. "Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin." Tetrahedron 79 (January 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, and Huawu Shao. "Synthesis of N-Substituted Iminosugar C-Glycosides and Evaluation as Promising α-Glucosidase Inhibitors." Molecules 27, no. 17 (August 27, 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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47

Szcześniak, Piotr, Barbara Grzeszczyk, and Bartłomiej Furman. "A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams." Molecules 26, no. 18 (September 8, 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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48

Liu, Hai-Qian, Cheng-Cheng Song, You-Hong Niu, Tao Li, Qin Li, and 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, and 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, and Murielle Muzard. "Iminosugars as glycosyltransferase inhibitors: synthesis of polyhydroxypyrrolidines and their evaluation on chitin synthase activity." European Journal of Medicinal Chemistry 40, no. 12 (December 2005): 1255–61. http://dx.doi.org/10.1016/j.ejmech.2005.07.001.

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