Articles de revues : « Bioisosterie »

1

Siebert, Carsten D. « Das Bioisosterie-Konzept : Arzneistoffentwicklung ». Chemie in unserer Zeit 38, n^o 5 (octobre 2004) : 320–24. http://dx.doi.org/10.1002/ciuz.200400331.

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Vink, Guillaume, Jean-Christophe Nebel et Stephen P. Wren. « In silico design of bioisosteric modifications of drugs for the treatment of diabetes ». Future Medicinal Chemistry 13, n^o 8 (avril 2021) : 691–700. http://dx.doi.org/10.4155/fmc-2020-0374.

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Aim: To identify virtual bioisosteric replacements of two GPR40 agonists. Materials & methods: Bioinformatic docking of candidate molecules featuring a wide range of carboxylic acid bioisosteres into complex with GPR40 was performed using TAK-875 and GW9508 templates. Results: This study suggests that 2,6-difluorophenol and squaric acid motifs are the preferred bioisosteric groups for conferring GPR40 affinity. Conclusion: This study suggests that compounds 10 and 20 are worthy synthetic targets.

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Hao, Xin, Xiangyu Qin, Xin Zhang, Bing Ma, Gang Qi, Taiming Yu, Zhongfei Han et Changjin Zhu. « Identification of quinoxalin-2(1H)-one derivatives as a novel class of multifunctional aldose reductase inhibitors ». Future Medicinal Chemistry 11, n^o 23 (décembre 2019) : 2989–3004. http://dx.doi.org/10.4155/fmc-2019-0194.

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Aim: Targeting aldose reductase and oxidative stress with quinoxalin-2(1 H)-one derivatives having a 1-hydroxypyrazole head as the bioisosteric replacement of carboxylic acid. Methodology & results: Aldose reductase inhibition, selectivity and antioxidant potency of all the synthesized compounds were evaluated, and binding modes were studied by molecular docking. Most of the derivatives showed potent and selective aldose reductase inhibition, and among them 13d was the most active (IC50 = 0.107 μM), suggesting success of the bioisosteric strategy. Phenolic 3,4-dihydroxyl compound 13f showed strong antioxidant ability even comparable to that of the well-known antioxidant Trolox. Conclusion: The present study identified the excellent bioisostere of the 1-hydroxypyrazole head group along with phenolic hydroxyl and vinyl spacer in C3 side chain on constructing quinoxalinone-based multifunctional aldose reductase inhibitors.

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Oebbeke, Matthias, Christof Siefker, Björn Wagner, Andreas Heine et Gerhard Klebe. « Fragment‐Bindung an die Kinase‐Scharnier‐Region : Wenn Ladungsverteilung und lokale p K a ‐Verschiebungen etablierte Bioisosterie‐Konzepte fehlleiten ». Angewandte Chemie 133, n^o 1 (29 octobre 2020) : 256–62. http://dx.doi.org/10.1002/ange.202011295.

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Agouram, Naima, El Mestafa El Hadrami et Abdeslem Bentama. « 1,2,3-Triazoles as Biomimetics in Peptide Science ». Molecules 26, n^o 10 (14 mai 2021) : 2937. http://dx.doi.org/10.3390/molecules26102937.

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Natural peptides are an important class of chemical mediators, essential for most vital processes. What limits the potential of the use of peptides as drugs is their low bioavailability and enzymatic degradation in vivo. To overcome this limitation, the development of new molecules mimicking peptides is of great importance for the development of new biologically active molecules. Therefore, replacing the amide bond in a peptide with a heterocyclic bioisostere, such as the 1,2,3-triazole ring, can be considered an effective solution for the synthesis of biologically relevant peptidomimetics. These 1,2,3-triazoles may have an interesting biological activity, because they behave as rigid link units, which can mimic the electronic properties of amide bonds and show bioisosteric effects. Additionally, triazole can be used as a linker moiety to link peptides to other functional groups.

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Chen, Guanglin, Ziran Jiang, Qiang Zhang, Guangdi Wang et Qiao-Hong Chen. « New Zampanolide Mimics : Design, Synthesis, and Antiproliferative Evaluation ». Molecules 25, n^o 2 (15 janvier 2020) : 362. http://dx.doi.org/10.3390/molecules25020362.

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Zampanolide is a promising microtubule-stabilizing agent (MSA) with a unique chemical structure. It is superior to the current clinically used MSAs due to the covalent nature of its binding to β-tubulin and high cytotoxic potency toward multidrug-resistant cancer cells. However, its further development as a viable drug candidate is hindered by its limited availability. More importantly, conversion of its chemically fragile side chain into a stabilized bioisostere is envisioned to enable zampanolide to possess more drug-like properties. As part of our ongoing project aiming to develop its mimics with a stable side chain using straightforward synthetic approaches, 2-fluorobenzyl alcohol was designed as a bioisosteric surrogate for the side chain based on its binding conformation as confirmed by the X-ray structure of tubulin complexed with zampanolide. Two new zampanolide mimics with the newly designed side chain have been successfully synthesized through a 25-step chemical transformation for each. Yamaguchi esterification and intramolecular Horner–Wadsworth–Emmons condensation were used as key reactions to construct the lactone core. The chiral centers at C17 and C18 were introduced by the Sharpless asymmetric dihydroxylation. Our WST-1 cell proliferation assay data in both docetaxel-resistant and docetaxel-naive prostate cancer cell lines revealed that compound 6 is the optimal mimic and the newly designed side chain can serve as a bioisostere for the chemically fragile N-acetyl hemiaminal side chain in zampanolide.

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Yous, Said, Patrick Depreux et Pierre Renard. « Synthesis of the Naphthalenic Bioisostere of Indorenate. Synthese des Naphthalin-Bioisosters von Indorenat ». Archiv der Pharmazie 326, n^o 2 (1993) : 119–20. http://dx.doi.org/10.1002/ardp.19933260210.

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8

Qiu, Jian, Scott H. Stevenson, Michael J. O'Beirn et Richard B. Silverman. « 2,6-Difluorophenol as a Bioisostere of a Carboxylic Acid : Bioisosteric Analogues of γ-Aminobutyric Acid ». Journal of Medicinal Chemistry 42, n^o 2 (janvier 1999) : 329–32. http://dx.doi.org/10.1021/jm980435l.

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Qiu, Jian, Scott H. Stevenseon, Michael J. O'Beirne et Richard B. Silverman. « ChemInform Abstract : 2,6-Difluorophenol as a Bioisostere of a Carboxylic Acid : Bioisosteric Analogues of γ-Aminobutyric Acid. » ChemInform 30, n^o 23 (15 juin 2010) : no. http://dx.doi.org/10.1002/chin.199923107.

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10

Dick, Alexej, et Simon Cocklin. « Bioisosteric Replacement as a Tool in Anti-HIV Drug Design ». Pharmaceuticals 13, n^o 3 (28 février 2020) : 36. http://dx.doi.org/10.3390/ph13030036.

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Bioisosteric replacement is a powerful tool for modulating the drug-like properties, toxicity, and chemical space of experimental therapeutics. In this review, we focus on selected cases where bioisosteric replacement and scaffold hopping have been used in the development of new anti-HIV-1 therapeutics. Moreover, we cover field-based, computational methodologies for bioisosteric replacement, using studies from our group as an example. It is our hope that this review will serve to highlight the utility and potential of bioisosteric replacement in the continuing search for new and improved anti-HIV drugs.

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11

Shan, Jinwen, et Changge Ji. « MolOpt : A Web Server for Drug Design using Bioisosteric Transformation ». Current Computer-Aided Drug Design 16, n^o 4 (3 septembre 2020) : 460–66. http://dx.doi.org/10.2174/1573409915666190704093400.

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Background: Bioisosteric replacement is widely used in drug design for lead optimization. However, the identification of a suitable bioisosteric group is not an easy task. Methods: In this work, we present MolOpt, a web server for in silico drug design using bioisosteric transformation. Potential bioisosteric transformation rules were derived from data mining, deep generative machine learning and similarity comparison. MolOpt tries to assist the medicinal chemist in his/her search for what to make next. Results and Discussion: By replacing molecular substructures with similar chemical groups, MolOpt automatically generates lists of analogues. MolOpt also evaluates forty important pharmacokinetic and toxic properties for each newly designed molecule. The transformed analogues can be assessed for possible future study. Conclusion: MolOpt is useful for the identification of suitable lead optimization ideas. The MolOpt Server is freely available for use on the web at http://xundrug.cn/molopt.

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12

Biot, Christophe, Holger Bauer, R. Heiner Schirmer et Elisabeth Davioud-Charvet. « 5-Substituted Tetrazoles as Bioisosteres of Carboxylic Acids. Bioisosterism and Mechanistic Studies on Glutathione Reductase Inhibitors as Antimalarials ». Journal of Medicinal Chemistry 47, n^o 24 (novembre 2004) : 5972–83. http://dx.doi.org/10.1021/jm0497545.

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13

Bathula, Chandramohan, Rajinikanth Mamidala, Chiranjeevi Thulluri, Rahul Agarwal, Kunal Kumar Jha, Parthapratim Munshi, Uma Adepally, Ashutosh Singh, M. Thirumala Chary et Subhabrata Sen. « Substituted furopyridinediones as novel inhibitors of α-glucosidase ». RSC Advances 5, n^o 110 (2015) : 90374–85. http://dx.doi.org/10.1039/c5ra19255b.

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14

Zhao, Qian, Annemilaï Tijeras-Raballand, Armand de Gramont, Eric Raymond et Laurent Désaubry. « Bioisosteric modification of flavaglines ». Tetrahedron Letters 57, n^o 26 (juin 2016) : 2943–44. http://dx.doi.org/10.1016/j.tetlet.2016.05.089.

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15

Wassermann, Anne Mai, et Jürgen Bajorath. « Identification of target family directed bioisosteric replacements ». MedChemComm 2, n^o 7 (2011) : 601–6. http://dx.doi.org/10.1039/c1md00066g.

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16

Saha, Abhishek, Subhankar Panda, Saurav Paul et Debasis Manna. « Phosphate bioisostere containing amphiphiles : a novel class of squaramide-based lipids ». Chemical Communications 52, n^o 60 (2016) : 9438–41. http://dx.doi.org/10.1039/c6cc04089f.

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17

Adams, Muneebah, Tameryn Stringer, Carmen de Kock, Peter J. Smith, Kirkwood M. Land, Nicole Liu, Christina Tam et al. « Bioisosteric ferrocenyl-containing quinolines with antiplasmodial and antitrichomonal properties ». Dalton Transactions 45, n^o 47 (2016) : 19086–95. http://dx.doi.org/10.1039/c6dt03175g.

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18

Bathula, Chandramohan, Shreemoyee Ghosh, Santanu Hati, Sayantan Tripathy, Shailja Singh, Saikat Chakrabarti et Subhabrata Sen. « Bioisosteric modification of known fucosidase inhibitors to discover a novel inhibitor of α-l-fucosidase ». RSC Advances 7, n^o 6 (2017) : 3563–72. http://dx.doi.org/10.1039/c6ra24939f.

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19

Staroń, Jakub, Dawid Warszycki, Justyna Kalinowska-Tłuścik, Grzegorz Satała et Andrzej J. Bojarski. « Rational design of 5-HT6R ligands using a bioisosteric strategy : synthesis, biological evaluation and molecular modelling ». RSC Advances 5, n^o 33 (2015) : 25806–15. http://dx.doi.org/10.1039/c5ra00054h.

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20

Baumeister, Sören, Dirk Schepmann et Bernhard Wünsch. « Synthesis and receptor binding of thiophene bioisosteres of potent GluN2B ligands with a benzo[7]annulene-scaffold ». MedChemComm 10, n^o 2 (2019) : 315–25. http://dx.doi.org/10.1039/c8md00545a.

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21

Chen, Guanglin, Manee Patanapongpibul, Ziran Jiang, Qiang Zhang, Shilong Zheng, Guangdi Wang, James D. White et Qiao-Hong Chen. « Synthesis and antiproliferative evaluation of new zampanolide mimics ». Organic & ; Biomolecular Chemistry 17, n^o 15 (2019) : 3830–44. http://dx.doi.org/10.1039/c9ob00556k.

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22

Henderson, Jaclyn L., Aarti Sawant-Basak, Jamison B. Tuttle, Amy B. Dounay, Laura A. McAllister, Jayvardhan Pandit, Suobao Rong et al. « Discovery of hydroxamate bioisosteres as KAT II inhibitors with improved oral bioavailability and pharmacokinetics ». MedChemComm 4, n^o 1 (2013) : 125–29. http://dx.doi.org/10.1039/c2md20166f.

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23

Kaur, Gurminder, Kawaljit Singh, Elumalai Pavadai, Mathew Njoroge, Marlene Espinoza-Moraga, Carmen De Kock, Peter J. Smith, Sergio Wittlin et Kelly Chibale. « Synthesis of fusidic acid bioisosteres as antiplasmodial agents and molecular docking studies in the binding site of elongation factor-G ». MedChemComm 6, n^o 11 (2015) : 2023–28. http://dx.doi.org/10.1039/c5md00343a.

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24

Liu, Yang, Lin Guo, Hongliang Duan, Liming Zhang, Neng Jiang, Xuechu Zhen et Jianhua Shen. « Discovery of 4-benzoylpiperidine and 3-(piperidin-4-yl)benzo[d]isoxazole derivatives as potential and selective GlyT1 inhibitors ». RSC Advances 5, n^o 51 (2015) : 40964–77. http://dx.doi.org/10.1039/c5ra04714e.

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25

Tommasi, Sara, Chiara Zanato, Benjamin C. Lewis, Pramod C. Nair, Sergio Dall'Angelo, Matteo Zanda et Arduino A. Mangoni. « Arginine analogues incorporating carboxylate bioisosteric functions are micromolar inhibitors of human recombinant DDAH-1 ». Organic & ; Biomolecular Chemistry 13, n^o 46 (2015) : 11315–30. http://dx.doi.org/10.1039/c5ob01843a.

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Arginine analogues incorporating carboxylate bioisosteric functional groups exhibit low micromolar inhibitory potential against human dimethylarginine dimethylaminohydrolase (DDAH), a key enzyme in the nitric oxide pathway.

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26

Duncton, Matthew A. J., Ryan B. Murray, Gary Park et Rajinder Singh. « Tetrazolone as an acid bioisostere : application to marketed drugs containing a carboxylic acid ». Organic & ; Biomolecular Chemistry 14, n^o 39 (2016) : 9343–47. http://dx.doi.org/10.1039/c6ob01646d.

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27

Wagener, Markus, et Jos P. M. Lommerse. « The Quest for Bioisosteric Replacements ». Journal of Chemical Information and Modeling 46, n^o 2 (mars 2006) : 677–85. http://dx.doi.org/10.1021/ci0503964.

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28

Erdeljac, Nathalie, Gerald Kehr, Marie Ahlqvist, Laurent Knerr et Ryan Gilmour. « Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE) : attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis ». Chemical Communications 54, n^o 85 (2018) : 12002–5. http://dx.doi.org/10.1039/c8cc05643a.

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29

Ouyang, Han, Chuan Fu, Songsen Fu, Zhe Ji, Ying Sun, Peiran Deng et Yufen Zhao. « Development of a stable phosphoarginine analog for producing phosphoarginine antibodies ». Organic & ; Biomolecular Chemistry 14, n^o 6 (2016) : 1925–29. http://dx.doi.org/10.1039/c5ob02603b.

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30

Dick, Benjamin L., Ashay Patel et Seth M. Cohen. « Effect of heterocycle content on metal binding isostere coordination ». Chemical Science 11, n^o 26 (2020) : 6907–14. http://dx.doi.org/10.1039/d0sc02717k.

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31

Swarbrick, Joanna M., Richard Graeff, Clive Garnham, Mark P. Thomas, Antony Galione et Barry V. L. Potter. « ‘Click cyclic ADP-ribose’ : a neutral second messenger mimic ». Chem. Commun. 50, n^o 19 (2014) : 2458–61. http://dx.doi.org/10.1039/c3cc49249d.

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Neutral synthetic analogues of the second messenger cADPR with a 1,2,3-triazole pyrophosphate bioisostere retain the ability to activate Ca²⁺release and to inhibit hydrolysis of cADPR by CD38.

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32

Dudkin, V. Y. « Bioisosteric equivalence of five-membered heterocycles ». Chemistry of Heterocyclic Compounds 48, n^o 1 (avril 2012) : 27–32. http://dx.doi.org/10.1007/s10593-012-0964-8.

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33

Burgos-Lepley, Carmen E., Lisa R. Thompson, Clare O. Kneen, Simon A. Osborne, Justin S. Bryans, Thomas Capiris, Nirmala Suman-Chauhan et al. « Carboxylate bioisosteres of gabapentin ». Bioorganic & ; Medicinal Chemistry Letters 16, n^o 9 (mai 2006) : 2333–36. http://dx.doi.org/10.1016/j.bmcl.2005.05.016.

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34

Edge, Colin. « Theoretical studies on bioisosteres ». Journal of Molecular Graphics 8, n^o 1 (mars 1990) : 57. http://dx.doi.org/10.1016/0263-7855(90)80072-n.

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35

Schwarz, Jacob B., Norman L. Colbry, Zhijian Zhu, Brian Nichelson, Nancy S. Barta, Kristin Lin, Raymond A. Hudack et al. « Carboxylate bioisosteres of pregabalin ». Bioorganic & ; Medicinal Chemistry Letters 16, n^o 13 (juillet 2006) : 3559–63. http://dx.doi.org/10.1016/j.bmcl.2006.03.083.

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36

Ratni, H., K. Baumann, P. Bellotti, X. A. Cook, L. G. Green, T. Luebbers, M. Reutlinger, A. F. Stepan et W. Vifian. « Phenyl bioisosteres in medicinal chemistry : discovery of novel γ-secretase modulators as a potential treatment for Alzheimer's disease ». RSC Medicinal Chemistry 12, n^o 5 (2021) : 758–66. http://dx.doi.org/10.1039/d1md00043h.

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We propose the use of a bridged piperidine moiety as a phenyl bioisostere, leading to strongly improved drug like properties. This concept was applied to the discovery of γ-secretase modulators for the potential treatment of Alzheimer's disease.

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37

B., Unterhalt, et Adam T. « 1-(4-Biphenylyl)ethylnitramine, bioisostere Profene ». Scientia Pharmaceutica 70, n^o 4 (5 décembre 2002) : 353–58. http://dx.doi.org/10.3797/scipharm.aut-02-34.

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38

Mykhailiuk, Pavel K. « Saturated bioisosteres of benzene : where to go next ? » Organic & ; Biomolecular Chemistry 17, n^o 11 (2019) : 2839–49. http://dx.doi.org/10.1039/c8ob02812e.

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39

Downey, A. Michael, et Christopher W. Cairo. « Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres ». Med. Chem. Commun. 5, n^o 11 (2014) : 1619–33. http://dx.doi.org/10.1039/c4md00255e.

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40

Staroń, Jakub, Dawid Warszycki, Rafał Kurczab, Grzegorz Satała, Ryszard Bugno, Adam Hogendorf et Andrzej J. Bojarski. « Halogen bonding enhances activity in a series of dual 5-HT6/D2 ligands designed in a hybrid bioisostere generation/virtual screening protocol ». RSC Advances 6, n^o 60 (2016) : 54918–25. http://dx.doi.org/10.1039/c6ra08714k.

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A hybrid bioisostere generation/virtual screening method combined with narrowing of chemical space through similarity to compounds that are active at the second target was successfully applied for the development of dual 5-HT₆/D₂ receptor ligands.

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41

Hevey, Rachel. « Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design ». Biomimetics 4, n^o 3 (28 juillet 2019) : 53. http://dx.doi.org/10.3390/biomimetics4030053.

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The aberrant presentation of carbohydrates has been linked to a number of diseases, such as cancer metastasis and immune dysregulation. These altered glycan structures represent a target for novel therapies by modulating their associated interactions with neighboring cells and molecules. Although these interactions are highly specific, native carbohydrates are characterized by very low affinities and inherently poor pharmacokinetic properties. Glycomimetic compounds, which mimic the structure and function of native glycans, have been successful in producing molecules with improved pharmacokinetic (PK) and pharmacodynamic (PD) features. Several strategies have been developed for glycomimetic design such as ligand pre-organization or reducing polar surface area. A related approach to developing glycomimetics relies on the bioisosteric replacement of carbohydrate functional groups. These changes can offer improvements to both binding affinity (e.g., reduced desolvation costs, enhanced metal chelation) and pharmacokinetic parameters (e.g., improved oral bioavailability). Several examples of bioisosteric modifications to carbohydrates have been reported; this review aims to consolidate them and presents different possibilities for enhancing core interactions in glycomimetics.

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Chen, Deheng, Dexiang Guo, Ziqin Yan et Yujun Zhao. « Allenamide as a bioisostere of acrylamide in the design and synthesis of targeted covalent inhibitors ». MedChemComm 9, n^o 2 (2018) : 244–53. http://dx.doi.org/10.1039/c7md00571g.

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Mittal, Rupali, Amit Kumar et Satish Kumar Awasthi. « Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst ». RSC Advances 11, n^o 19 (2021) : 11166–76. http://dx.doi.org/10.1039/d1ra01053k.

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Bubenyák, Máté, Mária Takács, Balázs Blazics, Ákos Rácz, Béla Noszál, László Püski, József Kökösi et István Hermecz. « Synthesis of bioisosteric 5-sulfa-rutaecarpine derivatives ». Arkivoc 2010, n^o 11 (7 novembre 2010) : 291–302. http://dx.doi.org/10.3998/ark.5550190.0011.b23.

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Mugnaini, C., S. Pasquini et F. Corelli. « The Bioisosteric Concept Applied to Cannabinoid Ligands ». Current Medicinal Chemistry 19, n^o 28 (1 octobre 2012) : 4794–815. http://dx.doi.org/10.2174/092986712803341575.

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IEMURA, Ryuichi, Manabu HORI, Tadayuki SAITO et Hiroshi OHTAKA. « Bioisosteric transformation of H1-antihistaminic benzimidazole derivatives. » CHEMICAL & ; PHARMACEUTICAL BULLETIN 37, n^o 10 (1989) : 2723–26. http://dx.doi.org/10.1248/cpb.37.2723.

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Warszycki, Dawid, Stefan Mordalski, Jakub Staroń et Andrzej J. Bojarski. « Bioisosteric Matrices for Ligands of Serotonin Receptors ». ChemMedChem 10, n^o 4 (13 mars 2015) : 601–5. http://dx.doi.org/10.1002/cmdc.201402563.

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48

Tomaszewski, Zbigniew, Michael P. Johnson, Xuemei Huang et David E. Nichols. « Benzofuran bioisosteres of hallucinogenic tryptamines ». Journal of Medicinal Chemistry 35, n^o 11 (mai 1992) : 2061–64. http://dx.doi.org/10.1021/jm00089a017.

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49

Goldring, Alastair O., Ian H. Gilbert, Naheed Mahmood et Jan Balzarini. « Lipophilic bioisosteres of nucleoside triphosphates ». Bioorganic & ; Medicinal Chemistry Letters 6, n^o 20 (octobre 1996) : 2411–16. http://dx.doi.org/10.1016/0960-894x(96)00443-x.

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VANMIDDLESWORTH, FRANK, JIM MILLIGAN, KEN BARTIZAL, CLAUDE DUFRESNE, JAN ONISHI, GEORGE ABRUZZO, ART PATCHETT et KEN WILSON. « Carbazate as a Glycine Bioisostere in Restricticin. » Journal of Antibiotics 49, n^o 3 (1996) : 329–31. http://dx.doi.org/10.7164/antibiotics.49.329.

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Articles de revues sur le sujet « Bioisosterie »

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