Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

MedChemComm

Volumn 4, Issue 5, 2013, Pages 783-791

  Wang, Jen Tsung ^a   Lin, Ting Chien ^b   Chen, Ying Hsuan ^a   Lin, Chun Hung ^b   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 HYDROXY 5 (HYDROXYMETHYL)PYRROLIDIN 2 CARBAMIDO]ETHYLPHOSPHONATE; 2 OXAPYRROLIZIDINE DERIVATIVE; 2,5 BIS(HYDROXYMETHYL) 3 HYDROXYPYRROLIDINE; 4 HYDROXY 5 (HYDROXYMETHYL)PYRROLIDINE 2 CARBOXYLATE; [4 HYDROXY 5 (HYDROXYMETHYL)PYRROLIDIN 2 YL]METHYL PHOSPHATE; ALPHA GALACTOSIDASE; BENZYL 3 HYDROXY 2 HYDROXYMETHYL 5 (IODOMETHYL)PYRROLIDINE 1 CARBOXYLATE; BETA GLUCOSIDASE; BIS(DIHYDROXYMETHYL)DIHYDROXYPYRROLIDINE; BULGENCIN A; CARBAMATE GROUP; CARBOXYLIC ACID; DEXTRO SERINE; FUNCTIONAL GROUP; GLYCOSIDASE INHIBITOR; HYACINTHACINE A2; IODOMETHYL GROUP; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; POLYHYDROXYLATED PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL;

EID: 84877298106     PISSN: 20402503     EISSN: 20402511     Source Type: Journal    
DOI: 10.1039/c3md00033h     Document Type: Article

References (32)

1. R. A. Dwek T. D. Butters F. M. Platt N. Zitzmann Nat. Rev. Drug Discovery 2002 1 65 75
2. N. Asano Glycobiology 2003 13 93R 104R
3. S. Gerber-Lemaire L. Juillerat-Jeanneret Mini-Rev. Med. Chem. 2006 6 1043 1052
4. N. Asano Cell. Mol. Life Sci. 2009 66 1479 1492
5. T. Kajimoto M. Node Curr. Top. Med. Chem. 2009 9 13 33
6. N. S. H. N. Moorthy M. J. Ramos P. A. Fernandes Mini-Rev. Med. Chem. 2012 12 713 720
7. L. J. Scott C. M. Spencer Drugs 2000 59 521 549
8. D. Durantel Curr. Opin. Invest. Drugs 2009 10 860 870
9. C. J. Dunn K. L. Goa Drugs 1999 58 761 784
10. K. McClellan C. M. Perry Drugs 2001 61 263 283
11. A. C. Schmidt Drugs 2004 64 2031 2046
12. A. Moscona N. Engl. J. Med. 2005 353 1363 1373
13. E. De Clercq Nat. Rev. Drug Discovery 2006 5 1015 1025
14. T.-W. Liu C.-W. Ho H.-H. Huang S.-M. Chang S. D. Popat Y.-T. Wang M.-S. Wu Y.-J. Chen C.-H. Lin Proc. Natl. Acad. Sci. U. S. A. 2009 106 14581 14586
15. A. A. Watson G. W. J. Fleet N. Asano R. J. Molyneux R. J. Nash Phytochemistry 2001 56 265 295
16. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, ed., A. E. Stütz, Wiley-VCH, Weinheim, 1999
17. N. Asano R. J. Nash R. J. Molyneux W. J. G. Fleet Tetrahedron: Asymmetry 2000 11 1645 1680
18. T. M. Wrodnigg A. J. Steiner B. J. Ueberbacher Anti-Cancer Agents Med. Chem. 2008 8 77 85
19. K. Suzuki T. Nakahara O. Kanie Curr. Top. Med. Chem. 2009 9 34 57
20. T. M. Wrodnigg A. E. Stütz Curr. Enzyme Inhib. 2012 8 47 99
21. C. S. Rye S. G. Withers Curr. Opin. Chem. Biol. 2000 4 573 580
22. A. Vasella G. J. Davies M. Böhm Curr. Opin. Chem. Biol. 2002 6 619 629
23. B. M. Trost D. B. Horne M. J. Woltering Chem.-Eur. J. 2006 12 6607 6620
24. J. K. Khalaf A. Datta J. Org. Chem. 2004 69 387 390
25. S. Desvergnes S. Py Y. Vallée J. Org. Chem. 2005 70 1459 1462
26. P. H. J. Carlsen T. Katsuki V. S. Martin K. B. Sharpless J. Org. Chem. 1981 46 3936 3938
27. T. M. Wrodnigg F. Diness C. Gruber H. Häusler I. Lundt K. Rupitz A. J. Steiner A. E. Stütz C. A. Tarling S. G. Withers H. Wölfler Bioorg. Med. Chem. 2004 12 3485 3495
28. Z. Fujimoto S. Kaneko M. Momma H. Kobayashi H. Mizuno J. Biol. Chem. 2003 278 20313 20318
29. G. M. Morris R. Huey W. Lindstrom M. F. Sanner R. K. Belew D. S. Goodsell A. J. Olson J. Comput. Chem. 2009 30 2785 2791
30. C. W. Reida N. T. Blackburnb B. A. Legareea F.-I. Auzanneaua A. J. Clarke FEBS Lett. 2004 574 73 79
31. S. J. Williams B. L. Mark D. J. Vocadlo M. N. James S. G. Withers J. Biol. Chem. 2002 277 40055 40065
32. A. W. Schuttelkopf D. M. van Aalten Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004 60 1355 1363