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Journal articles on the topic 'Trihydroxypiperidines'

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Author: Grafiati

Published: 10 March 2023

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1

Mirabella, S., G. Fibbi, C. Matassini, C. Faggi, A. Goti, and F. Cardona. "Accessing 2-substituted piperidine iminosugars by organometallic addition/intramolecular reductive amination: aldehyde vs. nitrone route." Organic & Biomolecular Chemistry 15, no. 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, and Michela I. Simone. "Synthetic Pathways to 3,4,5-Trihydroxypiperidines from the Chiral Pool." European Journal of Organic Chemistry 2018, no. 48 (November 27, 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, and Chu-Yi Yu. "Novel 2-aryl-3,4,5-trihydroxypiperidines: Synthesis and glycosidase inhibition." Chinese Chemical Letters 24, no. 12 (December 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, and Michela I. Simone. "Biological activities of 3,4,5-trihydroxypiperidines and their N - and O -derivatives." Chemical Biology & Drug Design 92, no. 1 (April 16, 2018): 1171–97. http://dx.doi.org/10.1111/cbdd.13182.

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5

Yu, Chu-Yi, and et al et al. "ChemInform Abstract: Novel 2-Aryl-3,4,5-trihydroxypiperidines: Synthesis and Glycosidase Inhibition." ChemInform 45, no. 18 (April 17, 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, and F. Cardona. "Glucocerebrosidase (GCase) activity modulation by 2-alkyl trihydroxypiperidines: Inhibition and pharmacological chaperoning." Bioorganic Chemistry 98 (May 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, and Francesca Cardona. "Stereoselective Synthesis of C-2 Alkylated Trihydroxypiperidines: Novel Pharmacological Chaperones for Gaucher Disease." ACS Medicinal Chemistry Letters 10, no. 4 (February 8, 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, and 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, no. 48 (November 27, 2018): 6830–42. http://dx.doi.org/10.1002/ejoc.201801011.

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9

Smith, Rachel D., and Neil R. Thomas. "A Convenient Synthesis of N-substituted Trihydroxypiperidines from Bis-Epoxides: Nucleophilic Opening of 1,2:4,5-Dianhydropentitols." Synlett 2000, no. 2 (February 2000): 193–96. http://dx.doi.org/10.1055/s-2000-6499.

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10

Smith, Rachel D., and 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, no. 21 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200021204.

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11

Matassini, Camilla, Stefania Mirabella, Andrea Goti, and 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, no. 21 (June 15, 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, and 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, no. 19 (October 2, 2020): 4526. http://dx.doi.org/10.3390/molecules25194526.

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Abstract:

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, and Kang Zhao. "N-Alkoxy Analogues of 3,4,5-Trihydroxypiperidine." Journal of Organic Chemistry 63, no. 19 (September 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, 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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15

Clemente, Francesca, Macarena Martínez-Bailén, Camilla Matassini, Amelia Morrone, Silvia Falliano, Anna Caciotti, Paolo Paoli, Andrea Goti, and Francesca Cardona. "Synthesis of a New β-Galactosidase Inhibitor Displaying Pharmacological Chaperone Properties for GM1 Gangliosidosis." Molecules 27, no. 13 (June 22, 2022): 4008. http://dx.doi.org/10.3390/molecules27134008.

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Abstract:

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, and K. ZHAO. "ChemInform Abstract: N-Alkoxy Analogues of 3,4,5-Trihydroxypiperidine." ChemInform 30, no. 6 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199906183.

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17

Lehmann, Jochen, and Beatrice Rob. "N-Amidino-3,4,5-trihydroxypiperidine, a new efficient competitive β-glucosidase inhibitor." Carbohydrate Research 272, no. 2 (August 1995): C11—C13. http://dx.doi.org/10.1016/0008-6215(95)00194-x.

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18

Ayers, Benjamin J., and George W. J. Fleet. "One-Pot Tandem Strecker Reaction and Iminocyclisations: Syntheses of Trihydroxypiperidine α-Iminonitriles." European Journal of Organic Chemistry 2014, no. 10 (January 28, 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, and Robert J. Nash. "Iminosugar Amino Acid idoBR1 Reduces Inflammatory Responses in Microglia." Molecules 27, no. 10 (May 23, 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., and George W. J. Fleet. "ChemInform Abstract: One-Pot Tandem Strecker Reaction and Iminocyclisations: Syntheses of Trihydroxypiperidine α-Iminonitriles." ChemInform 46, no. 5 (January 15, 2015): no. http://dx.doi.org/10.1002/chin.201505169.

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21

Falentin-Daudre, Céline, Daniel Beaupère, and Imane Stasik-Boutbaiba. "Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone." Carbohydrate Research 345, no. 14 (September 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, and Huawu Shao. "An efficient method for the stereoselective synthesis of N-substituted trihydroxypiperidine derivatives promoted by p-TsOH." Tetrahedron 72, no. 27-28 (July 2016): 3994–4000. http://dx.doi.org/10.1016/j.tet.2016.05.023.

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23

Bernotas, Ronald C., and Bruce Ganem. "Synthesis of 2S-carboxy-3R,4R,5S-trihydroxypiperidine; a naturally occurring inhibitor of β-D-glucuronidase." Tetrahedron Letters 26, no. 41 (January 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, and 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, no. 9 (August 10, 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, and 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, no. 48 (December 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, and 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, no. 5 (March 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, and Francesca Cardona. "3,4,5‐Trihydroxypiperidine Based Multivalent Glucocerebrosidase (GCase) Enhancers." ChemBioChem, April 7, 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, and Huawu Shao. "ChemInform Abstract: An Efficient Method for the Stereoselective Synthesis of N-Substituted Trihydroxypiperidine Derivatives Promoted by p-TsOH." ChemInform 47, no. 43 (October 2016). http://dx.doi.org/10.1002/chin.201643177.

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29

BERNOTAS, R. C., and B. GANEM. "ChemInform Abstract: Synthesis of 2S-Carboxy-3R,4R,5S-trihydroxypiperidine, a Naturally Occurring Inhibitor of β-D-Glucuronidase." Chemischer Informationsdienst 17, no. 7 (February 18, 1986). http://dx.doi.org/10.1002/chin.198607229.

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