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Artículos de revistas sobre el tema "Trihydroxypiperidines"

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1

Mirabella, S., G. Fibbi, C. Matassini, C. Faggi, A. Goti y F. Cardona. "Accessing 2-substituted piperidine iminosugars by organometallic addition/intramolecular reductive amination: aldehyde vs. nitrone route". Organic & Biomolecular Chemistry 15, n.º 43 (2017): 9121–26. http://dx.doi.org/10.1039/c7ob01848g.

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2

Wood, Adam, Kate L. Prichard, Zane Clarke, Todd A. Houston, George W. J. Fleet y Michela I. Simone. "Synthetic Pathways to 3,4,5-Trihydroxypiperidines from the Chiral Pool". European Journal of Organic Chemistry 2018, n.º 48 (27 de noviembre de 2018): 6812–29. http://dx.doi.org/10.1002/ejoc.201800943.

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3

Zhao, Hui, Wu-Bao Wang, Shinpei Nakagawa, Yue-Mei Jia, Xiang-Guo Hu, George W. J. Fleet, Francis X. Wilson, Robert J. Nash, Atsushi Kato y Chu-Yi Yu. "Novel 2-aryl-3,4,5-trihydroxypiperidines: Synthesis and glycosidase inhibition". Chinese Chemical Letters 24, n.º 12 (diciembre de 2013): 1059–63. http://dx.doi.org/10.1016/j.cclet.2013.06.027.

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4

Prichard, Kate, David Campkin, Nicholas O'Brien, Atsushi Kato, George W. J. Fleet y Michela I. Simone. "Biological activities of 3,4,5-trihydroxypiperidines and their N - and O -derivatives". Chemical Biology & Drug Design 92, n.º 1 (16 de abril de 2018): 1171–97. http://dx.doi.org/10.1111/cbdd.13182.

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5

Yu, Chu-Yi y et al et al. "ChemInform Abstract: Novel 2-Aryl-3,4,5-trihydroxypiperidines: Synthesis and Glycosidase Inhibition." ChemInform 45, n.º 18 (17 de abril de 2014): no. http://dx.doi.org/10.1002/chin.201418214.

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6

Clemente, F., C. Matassini, C. Faggi, S. Giachetti, C. Cresti, A. Morrone, P. Paoli, A. Goti, M. Martínez-Bailén y F. Cardona. "Glucocerebrosidase (GCase) activity modulation by 2-alkyl trihydroxypiperidines: Inhibition and pharmacological chaperoning". Bioorganic Chemistry 98 (mayo de 2020): 103740. http://dx.doi.org/10.1016/j.bioorg.2020.103740.

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7

Clemente, Francesca, Camilla Matassini, Andrea Goti, Amelia Morrone, Paolo Paoli y Francesca Cardona. "Stereoselective Synthesis of C-2 Alkylated Trihydroxypiperidines: Novel Pharmacological Chaperones for Gaucher Disease". ACS Medicinal Chemistry Letters 10, n.º 4 (8 de febrero de 2019): 621–26. http://dx.doi.org/10.1021/acsmedchemlett.8b00602.

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8

Prichard, Kate L., Nicholas O'Brien, Mahdi Ghorbani, Adam Wood, Evan Barnes, Atsushi Kato, Todd A. Houston y Michela I. Simone. "Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies toN- andO-Derivatisation". European Journal of Organic Chemistry 2018, n.º 48 (27 de noviembre de 2018): 6830–42. http://dx.doi.org/10.1002/ejoc.201801011.

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9

Smith, Rachel D. y Neil R. Thomas. "A Convenient Synthesis of N-substituted Trihydroxypiperidines from Bis-Epoxides: Nucleophilic Opening of 1,2:4,5-Dianhydropentitols". Synlett 2000, n.º 2 (febrero de 2000): 193–96. http://dx.doi.org/10.1055/s-2000-6499.

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10

Smith, Rachel D. y Neil R. Thomas. "ChemInform Abstract: A Convenient Synthesis of N-Substituted Trihydroxypiperidines from Bis-epoxides: Nucleophilic Opening of 1,2:4,5-Dianhydropentitols." ChemInform 31, n.º 21 (8 de junio de 2010): no. http://dx.doi.org/10.1002/chin.200021204.

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11

Matassini, Camilla, Stefania Mirabella, Andrea Goti y Francesca Cardona. "Double Reductive Amination and Selective Strecker Reaction of a D-Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5-Trihydroxypiperidines". European Journal of Organic Chemistry 2012, n.º 21 (15 de junio de 2012): 3920–24. http://dx.doi.org/10.1002/ejoc.201200587.

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12

Davighi, Maria Giulia, Francesca Clemente, Camilla Matassini, Amelia Morrone, Andrea Goti, Macarena Martínez-Bailén y Francesca Cardona. "Synthesis of “All-Cis” Trihydroxypiperidines from a Carbohydrate-Derived Ketone: Hints for the Design of New β-Gal and GCase Inhibitors". Molecules 25, n.º 19 (2 de octubre de 2020): 4526. http://dx.doi.org/10.3390/molecules25194526.

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Pharmacological chaperones (PCs) are small compounds able to rescue the activity of mutated lysosomal enzymes when used at subinhibitory concentrations. Nitrogen-containing glycomimetics such as aza- or iminosugars are known to behave as PCs for lysosomal storage disorders (LSDs). As part of our research into lysosomal sphingolipidoses inhibitors and looking in particular for new β-galactosidase inhibitors, we report the synthesis of a series of alkylated azasugars with a relative “all-cis” configuration at the hydroxy/amine-substituted stereocenters. The novel compounds were synthesized from a common carbohydrate-derived piperidinone intermediate 8, through reductive amination or alkylation of the derived alcohol. In addition, the reaction of ketone 8 with several lithium acetylides allowed the stereoselective synthesis of new azasugars alkylated at C-3. The activity of the new compounds towards lysosomal β-galactosidase was negligible, showing that the presence of an alkyl chain in this position is detrimental to inhibitory activity. Interestingly, 9, 10, and 12 behave as good inhibitors of lysosomal β-glucosidase (GCase) (IC50 = 12, 6.4, and 60 µM, respectively). When tested on cell lines bearing the Gaucher mutation, they did not impart any enzyme rescue. However, altogether, the data included in this work give interesting hints for the design of novel inhibitors.
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13

Sun, Lihong, Pan Li, Nduka Amankulor, Weiping Tang, Donald W. Landry y Kang Zhao. "N-Alkoxy Analogues of 3,4,5-Trihydroxypiperidine". Journal of Organic Chemistry 63, n.º 19 (septiembre de 1998): 6472–75. http://dx.doi.org/10.1021/jo971535m.

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14

Matassini, Camilla, Stefania Mirabella, Andrea Goti, Inmaculada Robina, Antonio J. Moreno-Vargas y Francesca Cardona. "Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar". Beilstein Journal of Organic Chemistry 11 (16 de diciembre de 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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15

Clemente, Francesca, Macarena Martínez-Bailén, Camilla Matassini, Amelia Morrone, Silvia Falliano, Anna Caciotti, Paolo Paoli, Andrea Goti y Francesca Cardona. "Synthesis of a New β-Galactosidase Inhibitor Displaying Pharmacological Chaperone Properties for GM1 Gangliosidosis". Molecules 27, n.º 13 (22 de junio de 2022): 4008. http://dx.doi.org/10.3390/molecules27134008.

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GM1 gangliosidosis is a rare lysosomal disease caused by the deficiency of the enzyme β-galactosidase (β-Gal; GLB1; E.C. 3.2.1.23), responsible for the hydrolysis of terminal β-galactosyl residues from GM1 ganglioside, glycoproteins, and glycosaminoglycans, such as keratan-sulfate. With the aim of identifying new pharmacological chaperones for GM1 gangliosidosis, the synthesis of five new trihydroxypiperidine iminosugars is reported in this work. The target compounds feature a pentyl alkyl chain in different positions of the piperidine ring and different absolute configurations of the alkyl chain at C-2 and the hydroxy group at C-3. The organometallic addition of a Grignard reagent onto a carbohydrate-derived nitrone in the presence or absence of a suitable Lewis Acid was exploited, providing structural diversity at C-2, followed by the ring-closure reductive amination step. An oxidation-reduction process allowed access to a different configuration at C-3. The N-pentyl trihydroxypiperidine iminosugar was also synthesized for the purpose of comparison. The biological evaluation of the newly synthesized compounds was performed on leucocyte extracts from healthy donors and identified two suitable β-Gal inhibitors, namely compounds 10 and 12. Among these, compound 12 showed chaperoning properties since it enhanced β-Gal activity by 40% when tested on GM1 patients bearing the p.Ile51Asn/p.Arg201His mutations.
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16

SUN, L., P. LI, N. AMANKULOR, W. TANG, D. W. LANDRY y K. ZHAO. "ChemInform Abstract: N-Alkoxy Analogues of 3,4,5-Trihydroxypiperidine." ChemInform 30, n.º 6 (17 de junio de 2010): no. http://dx.doi.org/10.1002/chin.199906183.

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17

Lehmann, Jochen y Beatrice Rob. "N-Amidino-3,4,5-trihydroxypiperidine, a new efficient competitive β-glucosidase inhibitor". Carbohydrate Research 272, n.º 2 (agosto de 1995): C11—C13. http://dx.doi.org/10.1016/0008-6215(95)00194-x.

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18

Ayers, Benjamin J. y George W. J. Fleet. "One-Pot Tandem Strecker Reaction and Iminocyclisations: Syntheses of Trihydroxypiperidine α-Iminonitriles". European Journal of Organic Chemistry 2014, n.º 10 (28 de enero de 2014): 2053–69. http://dx.doi.org/10.1002/ejoc.201301705.

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19

Olajide, Olumayokun A., Victoria U. Iwuanyanwu, Owolabi W. Banjo, Atsushi Kato, Yana B. Penkova, George W. J. Fleet y Robert J. Nash. "Iminosugar Amino Acid idoBR1 Reduces Inflammatory Responses in Microglia". Molecules 27, n.º 10 (23 de mayo de 2022): 3342. http://dx.doi.org/10.3390/molecules27103342.

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(1) Background. Inflammation is reported to be a key factor in neurodegeneration. The microglia are immune cells present in the central nervous system; their activation results in the release of inflammatory cytokines and is thought to be related to aging and neurodegenerative disorders, such as Alzheimer’s disease. (2) Methods. A mouse BV-2 microglia cell line was activated using LPS and the anti-inflammatory cucumber-derived iminosugar amino acid idoBR1, (2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid, was used alongside dexamethasone as the control to determine whether it could reduce the inflammatory responses. (3) Results. A dose-dependent reduction in the LPS-induced production of the proinflammatory factors TNFα, IL-6, and nitric oxide and the transcription factor NF-κB was found. (4) Conclusions. Further investigations of the anti-inflammatory effects of idoBR1 in other models of neurodegenerative diseases are warranted.
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20

Ayers, Benjamin J. y George W. J. Fleet. "ChemInform Abstract: One-Pot Tandem Strecker Reaction and Iminocyclisations: Syntheses of Trihydroxypiperidine α-Iminonitriles." ChemInform 46, n.º 5 (15 de enero de 2015): no. http://dx.doi.org/10.1002/chin.201505169.

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21

Falentin-Daudre, Céline, Daniel Beaupère y Imane Stasik-Boutbaiba. "Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone". Carbohydrate Research 345, n.º 14 (septiembre de 2010): 1983–87. http://dx.doi.org/10.1016/j.carres.2010.07.005.

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22

Yuan, Wen, Jianhui Xia, Xiaoke Zhang, Peng Liang, Jichao Zhang, Wei Jiao y Huawu Shao. "An efficient method for the stereoselective synthesis of N-substituted trihydroxypiperidine derivatives promoted by p-TsOH". Tetrahedron 72, n.º 27-28 (julio de 2016): 3994–4000. http://dx.doi.org/10.1016/j.tet.2016.05.023.

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23

Bernotas, Ronald C. y Bruce Ganem. "Synthesis of 2S-carboxy-3R,4R,5S-trihydroxypiperidine; a naturally occurring inhibitor of β-D-glucuronidase". Tetrahedron Letters 26, n.º 41 (enero de 1985): 4981–82. http://dx.doi.org/10.1016/s0040-4039(01)80831-5.

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24

Booth, Kathrine V., Sarah F. Jenkinson, David J. Watkin, Hazel Sharp, Paul Wyn Jones, Robert J. Nash y George W. J. Fleet. "(2S,3R,4R,5S)-3,4,5-Trihydroxypipecolic acid dihydrate [(2S,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid dihydrate]". Acta Crystallographica Section E Structure Reports Online 63, n.º 9 (10 de agosto de 2007): o3783—o3784. http://dx.doi.org/10.1107/s1600536807039281.

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25

Gajare, Vikas S., Sandip R. Khobare, Rajender Datrika, K. Srinivas Reddy, Nagaraju Rajana, Sarvesh Kumar, B. Venkateswara Rao y U. K. Syam Kumar. "Diversity oriented concise asymmetric synthesis of azasugars: a facile access to l -2,3- trans -3,4- cis -dihydroxyproline and (3 S ,5 S )-3,4,5-trihydroxypiperidine". Tetrahedron Letters 56, n.º 48 (diciembre de 2015): 6659–63. http://dx.doi.org/10.1016/j.tetlet.2015.10.013.

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26

Simone, Michela I., Raquel G. Soengas, Sarah F. Jenkinson, Emma L. Evinson, Robert J. Nash y George W. J. Fleet. "Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2". Tetrahedron: Asymmetry 23, n.º 5 (marzo de 2012): 401–8. http://dx.doi.org/10.1016/j.tetasy.2012.03.007.

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27

Vanni, Costanza, Francesca Clemente, Paolo Paoli, Amelia Morrone, Camilla Matassini, Andrea Goti y Francesca Cardona. "3,4,5‐Trihydroxypiperidine Based Multivalent Glucocerebrosidase (GCase) Enhancers". ChemBioChem, 7 de abril de 2022. http://dx.doi.org/10.1002/cbic.202200077.

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28

Yuan, Wen, Jianhui Xia, Xiaoke Zhang, Peng Liang, Jichao Zhang, Wei Jiao y Huawu Shao. "ChemInform Abstract: An Efficient Method for the Stereoselective Synthesis of N-Substituted Trihydroxypiperidine Derivatives Promoted by p-TsOH." ChemInform 47, n.º 43 (octubre de 2016). http://dx.doi.org/10.1002/chin.201643177.

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29

BERNOTAS, R. C. y B. GANEM. "ChemInform Abstract: Synthesis of 2S-Carboxy-3R,4R,5S-trihydroxypiperidine, a Naturally Occurring Inhibitor of β-D-Glucuronidase." Chemischer Informationsdienst 17, n.º 7 (18 de febrero de 1986). http://dx.doi.org/10.1002/chin.198607229.

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