Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

作者: Mathieu L Lepage , Alessandra Meli , Anne Bodlenner , Céline Tarnus , Francesco De Riccardis

DOI: 10.3762/BJOC.10.144

关键词:

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

参考文章(44)
Peter E. Nielsen, Pseudo-peptides in drug discovery Wiley-VCH. ,(2004)
Antoine Joosten, Jérémy P. Schneider, Mathieu L. Lepage, Céline Tarnus, Anne Bodlenner, Philippe Compain, A Convergent Strategy for the Synthesis of Second‐Generation Iminosugar Clusters Using “Clickable” Trivalent Dendrons European Journal of Organic Chemistry. ,vol. 2014, pp. 1866- 1872 ,(2014) , 10.1002/EJOC.201301583
Elena Moreno-Clavijo, Ana T. Carmona, Antonio J. Moreno-Vargas, Lidia Molina, Daniel W. Wright, Gideon J. Davies, Inmaculada Robina, Exploring a Multivalent Approach to α‐L‐Fucosidase Inhibition European Journal of Organic Chemistry. ,vol. 2013, pp. 7328- 7336 ,(2013) , 10.1002/EJOC.201300878
Christian W. Tornøe, Caspar Christensen, Morten Meldal, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. ,vol. 67, pp. 3057- 3064 ,(2002) , 10.1021/JO011148J
N. Maulucci, I. Izzo, G. Bifulco, A. Aliberti, C. De Cola, D. Comegna, C. Gaeta, A. Napolitano, C. Pizza, C. Tedesco, D. Flot, F. De Riccardis, Synthesis, structures, and properties of nine-, twelve-, and eighteen-membered N-benzyloxyethyl cyclic α-peptoids Chemical Communications. pp. 3927- 3929 ,(2008) , 10.1039/B806508J
Daniela Comegna, Monica Benincasa, Renato Gennaro, Irene Izzo, Francesco De Riccardis, Design, synthesis and antimicrobial properties of non-hemolytic cationic α-cyclopeptoids Bioorganic & Medicinal Chemistry. ,vol. 18, pp. 2010- 2018 ,(2010) , 10.1016/J.BMC.2010.01.026
Vasant V Ranade, Iminosugars-From Synthesis to Therapeutic Applications American Journal of Therapeutics. ,vol. 16, pp. 200- ,(2009) , 10.1097/MJT.0B013E318172886D
Mija Ahn, Ravichandran N. Murugan, Yong Hai Nan, Chaejoon Cheong, HoIk Sohn, Eun-Hee Kim, Eunha Hwang, Eun Kyoung Ryu, Shin Won Kang, Song Yub Shin, Jeong Kyu Bang, Substitution of the GalNAc-α-O-Thr11 residue in drosocin with O-linked glyco-peptoid residue: Effect on antibacterial activity and conformational change Bioorganic & Medicinal Chemistry Letters. ,vol. 21, pp. 6148- 6153 ,(2011) , 10.1016/J.BMCL.2011.08.012
Camille Decroocq, Antoine Joosten, Raphaël Sergent, Teresa Mena Barragán, Carmen Ortiz Mellet, Philippe Compain, The multivalent effect in glycosidase inhibition: probing the influence of valency, peripheral ligand structure, and topology with cyclodextrin-based iminosugar click clusters. ChemBioChem. ,vol. 14, pp. 2038- 2049 ,(2013) , 10.1002/CBIC.201300283
Norbert Sewald, Anna Norgren, Carsten Budke, Zsuzsa Majer, Carolin Heggemann, Thomas Koop, On-resin click-glycoconjugation of peptoids Synthesis. ,vol. 2009, pp. 488- 494 ,(2009) , 10.1055/S-0028-1083302