Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

Davide Bini, Francesca Cardona, Matilde Forcella, Camilla Parmeggiani, Paolo Parenti, Francesco Nicotra and Laura Cipolla
Beilstein J. Org. Chem. 2012, 8, 514–521. https://doi.org/10.3762/bjoc.8.58

Supporting Information

Supporting Information File 1: Full experimental data.
Format: PDF Size: 141.4 KB Download

Cite the Following Article

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors
Davide Bini, Francesca Cardona, Matilde Forcella, Camilla Parmeggiani, Paolo Parenti, Francesco Nicotra and Laura Cipolla
Beilstein J. Org. Chem. 2012, 8, 514–521. https://doi.org/10.3762/bjoc.8.58

How to Cite

Bini, D.; Cardona, F.; Forcella, M.; Parmeggiani, C.; Parenti, P.; Nicotra, F.; Cipolla, L. Beilstein J. Org. Chem. 2012, 8, 514–521. doi:10.3762/bjoc.8.58

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Kim, Y. S.; Boggu, P. R.; Kong, Y.; Park, G. M.; Kim, I. S.; Jung, Y. H. Total synthesis of α-1-C-propyl-3,6-di-epi-nojirimycin and polyhydroxyindolizidine alkaloids via regio- and diastereoselective amination of anomeric acetals. Tetrahedron 2022, 116, 132809. doi:10.1016/j.tet.2022.132809
  • Wang, J.-Z.; Cheng, B.; Kato, A.; Kise, M.; Shimadate, Y.; Jia, Y.-M.; Li, Y.-X.; Fleet, G. W. J.; Yu, C.-Y. Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives. European journal of medicinal chemistry 2022, 233, 114230. doi:10.1016/j.ejmech.2022.114230
  • Matassini, C.; Parmeggiani, C.; Cardona, F. New Frontiers on Human Safe Insecticides and Fungicides: An Opinion on Trehalase Inhibitors. Molecules (Basel, Switzerland) 2020, 25, 3013. doi:10.3390/molecules25133013
  • Sánchez-Fernández, E. M.; García-Moreno, M. I.; Fernández, J. M. G.; Mellet, C. O. sp2-Iminosugars as chemical mimics for glycodrug design. Small Molecule Drug Discovery; Elsevier, 2020; pp 197–224. doi:10.1016/b978-0-12-818349-6.00007-8
  • Shukla, E.; Thorat, L.; Bendre, A. D.; Jadhav, S.; Pal, J. K.; Nath, B. B.; Gaikwad, S. M. Cloning and characterization of trehalase: a conserved glycosidase from oriental midge, Chironomus ramosus. 3 Biotech 2018, 8, 352. doi:10.1007/s13205-018-1376-y
  • Ai, D.; Cheng, S.; Chang, H.; Yang, T.; Wang, G.; Yu, C. Gene Cloning, Prokaryotic Expression, and Biochemical Characterization of a Soluble Trehalase in Helicoverpa armigera Hübner (Lepidoptera: Noctuidae). Journal of insect science (Online) 2018, 18, 22. doi:10.1093/jisesa/iey056
  • D'Adamio, G.; Forcella, M.; Fusi, P.; Parenti, P.; Matassini, C.; Ferhati, X.; Vanni, C.; Cardona, F. Probing the Influence of Linker Length and Flexibility in the Design and Synthesis of New Trehalase Inhibitors. Molecules (Basel, Switzerland) 2018, 23, 436–453. doi:10.3390/molecules23020436
  • El-Hiti, G. A.; Abdel-Wahab, B. F.; Baashen, M.; Hegazy, A. S.; Kariuki, B. M. Crystal structure of (Z)-4-((E)-(4-chlorobenzyli-dene)hydrazono)-1-p-tolylpyrrolidine-3-carbonitrile, C19H17ClN4. Zeitschrift für Kristallographie - New Crystal Structures 2016, 231, 1109–1110. doi:10.1515/ncrs-2016-0079
  • Shukla, E.; Thorat, L.; Bhavnani, V.; Bendre, A. D.; Pal, J. K.; Nath, B. B.; Gaikwad, S. M. Molecular cloning and in silico studies of physiologically significant trehalase from Drosophila melanogaster. International journal of biological macromolecules 2016, 92, 282–292. doi:10.1016/j.ijbiomac.2016.06.097
  • Harit, V. K.; Ramesh, N. G. Amino-functionalized iminocyclitols: synthetic glycomimetics of medicinal interest. RSC Advances 2016, 6, 109528–109607. doi:10.1039/c6ra23513a
  • Cendret, V.; Legigan, T.; Mingot, A.; Thibaudeau, S.; Adachi, I.; Forcella, M.; Parenti, P.; Bertrand, J.; Becq, F.; Norez, C.; Désiré, J.; Kato, A.; Blériot, Y. Synthetic deoxynojirimycin derivatives bearing a thiolated, fluorinated or unsaturated N-alkyl chain: identification of potent α-glucosidase and trehalase inhibitors as well as F508del-CFTR correctors. Organic & biomolecular chemistry 2015, 13, 10734–10744. doi:10.1039/c5ob01526j
  • Mena-Barragán, T.; García-Moreno, M. I.; Nanba, E.; Higaki, K.; Concia, A. L.; Clapés, P.; Fernández, J. M. G.; Mellet, C. O. Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts. European journal of medicinal chemistry 2015, 121, 880–891. doi:10.1016/j.ejmech.2015.08.038
  • Parmeggiani, C.; Catarzi, S.; Matassini, C.; D'Adamio, G.; Morrone, A.; Goti, A.; De Paoli, P.; Cardona, F. Human Acid β-Glucosidase Inhibition by Carbohydrate Derived Iminosugars: Towards New Pharmacological Chaperones for Gaucher Disease. Chembiochem : a European journal of chemical biology 2015, 16, 2054–2064. doi:10.1002/cbic.201500292
  • de la Fuente, A.; Mena-Barragán, T.; Farrar-Tobar, R. A.; Verdaguer, X.; Fernández, J. M. G.; Mellet, C. O.; Riera, A. Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors. Organic & biomolecular chemistry 2015, 13, 6500–6510. doi:10.1039/c5ob00507h
  • Bini, D.; Sgambato, A.; Gabrielli, L.; Russo, L.; Cipolla, L. Biotechnology of Bioactive Compounds; Wiley, 2015; pp 345–369. doi:10.1002/9781118733103.ch14
  • D'Adamio, G.; Sgambato, A.; Forcella, M.; Caccia, S.; Parmeggiani, C.; Casartelli, M.; Parenti, P.; Bini, D.; Cipolla, L.; Fusi, P.; Cardona, F. New synthesis and biological evaluation of uniflorine A derivatives: towards specific insect trehalase inhibitors. Organic & biomolecular chemistry 2015, 13, 886–892. doi:10.1039/c4ob02016b
  • Shukla, E.; Thorat, L.; Nath, B. B.; Gaikwad, S. M. Insect trehalase: physiological significance and potential applications. Glycobiology 2014, 25, 357–367. doi:10.1093/glycob/cwu125
  • Lindhorst, T. K. Multivalent glycosystems for nanoscience. Beilstein journal of organic chemistry 2014, 10, 2345–2347. doi:10.3762/bjoc.10.244
  • Cipolla, L.; Sgambato, A.; Forcella, M.; Fusi, P.; Parenti, P.; Cardona, F.; Bini, D. N-Bridged 1-deoxynojirimycin dimers as selective insect trehalase inhibitors. Carbohydrate research 2014, 389, 46–49. doi:10.1016/j.carres.2013.12.025
  • Bansal, R.; Mian, M. A. R.; Mittapalli, O.; Michel, A. Molecular characterization and expression analysis of soluble trehalase gene in Aphis glycines, a migratory pest of soybean. Bulletin of entomological research 2013, 103, 286–295. doi:10.1017/s0007485312000697

Patents

  • PIETERS ROELOF JAN; MARTIN NATHANIEL ISAAC; BRANDERHORST HILBERT MARINUS; KOOIJ RAYMOND. UREA AND GUANIDINIUM DERIVATIVES OF IMINOSUGARS. WO 2014017915 A3, June 12, 2014.
  • PIETERS ROELOF JAN; MARTIN NATHANIEL ISAAC; BRANDERHORST HILBERT MARINUS; KOOIJ RAYMOND. UREA AND GUANIDINIUM DERIVATIVES OF IMINOSUGARS. WO 2014017915 A2, Jan 30, 2014.
Other Beilstein-Institut Open Science Activities