Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 6, 2011, Pages 2015-2022

  Xie, Weijia ^a,b   Tanabe, Genzoh ^a   Akaki, Junji ^a   Morikawa, Toshio ^a   Ninomiya, Kiyofumi ^a   Minematsu, Toshie ^a   Yoshikawa, Masayuki ^a   Wu, Xiaoming ^b   Muraoka, Osamu ^a  

^a KINKI UNIVERSITY   (Japan)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Glucosidase inhibitor; Neoponkoranol; Neosalaprinol; Salacia; SAR study

Indexed keywords

1,2:3,4 DI O ISOPROPYLIDENE 6 O TRIFLUOROMETHANESULFONYL ALPHA DEXTRO GALACTOPYRANOSE; 1,4 DIDEOXY 1,4 [(2,3,4,5,6 PENTAHYDROXYHEXYL)EPISULFONIUMYLIDENE] DEXTRO ARABINITOL CHLORIDE; 1,4 DIDEOXY 1,4[(2,3 DIHYDROXYPROPYL)EPISULFONIUMYLIDENE] DEXTRO ARABINITOL CHLORIDE; 2,3,5 TRI O BENZYL 1,4 DIDEOXY 1,4 [(1,2,3,4 TETRA O BENZYL 6 DEOXY ALPHA DEXTRO MANNOPYRANOS 6 YL)EPISULFONIUMYLIDENE]DEXTRO ARABINITOL TRIFLUOROMETHANESULFONATE; 2,3,5 TRI O BENZYL 1,4 DIDEOXY 1,4 [(1,2,3,4 TETRA O BENZYL 6 DEOXY BETA DEXTRO GLUCOPYRANOS 6 YL)EPISULFONIUMYLIDENE]DEXTRO ARABINITOL TRIFLUOROMETHANESULFONATE; 2,3,5 TRI O BENZYL 1,4 DIDEOXY 1,4 [(1,2:3,4 DI O ISOPROPYLIDENE 6 DEOXY ALPHA DEXTRO GALACTOPYRANOS 6 YL)EPISULFONIUMYLIDENE] DEXTRO ARABINITOL TRIFLUOROMETHANESULFONATE; 2,3,5 TRI O BENZYL 1,4 DIDEOXY 1,4 [(2,3 DIHYDROXYPROPYL)EPISULFONIUMYLIDENE] DEXTRO ARABINITOL CHLORIDE; 3,6 ANHYDROMANNOPYRANOSIDE; ACARBOSE; ALPHA GLUCOSIDASE INHIBITOR; ANTIDIABETIC AGENT; BENZYL 2,3,4 TRI O BENZYL 6 O TRIFLUOROMETHANESULFONYL ALPHA DEXTRO MANNOPYRANOSIDE; BENZYL 2,3,4 TRI O BENZYL 6 O TRIFLUOROMETHANESULFONYL BETA DEXTRO GLUCOPYRANOSIDE; KOTALANOL; MANNOSE; NEOKOTALANOL; NEOPONKORANOL; NEOSALACINOL; NEOSALAPRINOL; PLANT EXTRACT; PONKORANOL; SALACIA CHINENSIS EXTRACT; SALACINOL; SALAPRINOL; THIOSUGAR; THIOSUGAR SULFONIUM SALT; UNCLASSIFIED DRUG; VOGLIBOSE; WATER EXTRACT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COLUMN CHROMATOGRAPHY; CYCLIZATION; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; EPIMERIZATION; HUMAN; HYDROLYSIS; METHANOLYSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SALACIA; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SULFONATION;

ALPHA-GLUCOSIDASES; ANIMALS; ENZYME INHIBITORS; HYPOGLYCEMIC AGENTS; RATS; SALACIA; STRUCTURE-ACTIVITY RELATIONSHIP; SUGAR ALCOHOLS; THIOPHENES; THIOSUGARS;

RATTUS;

EID: 79952438320     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.01.052     Document Type: Article

References (42)

1. C.P. Kordik, and A.B. Reitz J. Med. Chem. 42 1999 181
2. P.E. Goss, M.A. Baker, J.P. Carver, and J.W. Dennis Clin. Cancer Res. 1 1995 935
3. Van den Broek, and A.G.M. Leon Carbohydr. Drug Design, New York 1997 471
4. T. Cox, R. Lachmann, C. Hollak, and J. Aerts Lancet 355 2000 1481
5. O.R. Martin, P. Compain, and H. Bentham Curr. Top. Med. Chem. 3 2003 120
6. P.E. Goss, C.L. Reid, D. Bailey, and J.W. Dennis Clin. Cancer Res. 3 1997 1077
7. S. Mohla, S. White, K. Grzegorzewski, D. Nielsen, G. Dunston, L. Dickson, J.K. Cha, A. Assea, and K. Olden Anticancer Res. 10 1990 1515
8. P.E. Goss, J. Baptiste, B. Fernandes, M. Baker, and J.W. Dennis Cancer Res. 54 1994 1450
9. D.E. Koshland Biol. Rev. 28 1953 416
10. J.D. McCarter, and S.G. Withers Curr. Opin. Struct. Biol. 4 1994 885
11. R.A. Dwek Chem. Rev. 96 1996 683
12. H. Yuasa, M. Izumi, and H. Hashimoto Yuki Gosei Kagaku Kyokaishi 60 2002 774
13. M. Yoshikawa, T. Murakami, H. Shimada, H. Matsuda, J. Yamahara, G. Tanabe, and O. Muraoka Tetrahedron Lett. 38 1997 8367
14. M. Yoshikawa, T. Morikawa, H. Matsuda, G. Tanabe, and O. Muraoka Bioorg. Med. Chem. 10 2002 1547
15. M. Yoshikawa, T. Murakami, K. Yashiro, and H. Matsuda Chem. Pharm. Bull. 46 1998 1339
16. M. Yoshikawa, F. Xu, S. Nakamura, T. Wang, H. Matsuda, G. Tanabe, and O. Muraoka Heterocycles 75 2008 1397
17. K. Jayakanthan, M.S. Sankar, and B.M. Pinto J. Am. Chem. Soc. 131 2009 5621
18. B.D. Johnston, H.H. Jensen, and B.M. Pinto J. Org. Chem. 71 2006 1111
19. G. Tanabe, M. Sakano, T. Minematsu, H. Matusda, M. Yoshikawa, and O. Muraoka Tetrahedron 64 2008 10080
20. O. Muraoka, W. Xie, S. Osaki, A. Kagawa, G. Tanabe, M.F.A. Amer, T. Minematsu, T. Morikawa, and M. Yoshikawa Tetrahedron 66 2010 3717
21. Recent review relevant to the work: S. Mohan, and B.M. Pinto Carbohydr. Res. 342 2007 1551
22. G. Tanabe, K. Matsuoka, T. Minematsu, T. Morikawa, K. Ninomiya, H. Matsuda, M. Yoshikawa, H. Murata, and O. Muraoka J. Pharm. Soc. Jpn. 127 2007 129
23. R. Nasi, B.O. Patrick, L. Sim, D.R. Rose, and B.M. Pinto J. Org. Chem. 73 2008 6172
24. G. Tanabe, T. Hatanaka, T. Minematsu, H. Matsuda, M. Yoshikawa, and O. Muraoka Heterocycles 79 2009 1093
25. S. Mohan, K. Jayakanthan, R. Nasi, D.A. Kuntz, D.R. Rose, and B.M. Pinto Org. Lett. 12 2010 1088
26. L. Sim, K. Jayakanthan, S. Mohan, R. Nasi, B.D. Johnston, B.M. Pinto, and D.R. Rose Biochemistry 49 2010 443
27. S. Nakamura, K. Takahira, G. Tanabe, T. Morikawa, M. Sakano, K. Ninomiya, M. Yoshikawa, O. Muraoka, and I. Nakanishi Bioorg. Med. Chem. Lett. 20 2010 4420
28. R. Eskandari, D.A. Kuntz, D.R. Rose, and B.M. Pinto Org. Lett. 12 2010 1632
29. R. Eskandari, K. Jayakanthan, D.A. Kuntz, D.R. Rose, and B.M. Pinto Bioorg. Med. Chem. 18 2010 2829
30. R. Eskandari, K. Jones, D.R. Rose, and B.M. Pinto Bioorg. Med. Chem. Lett. 20 2010 5686 and references cited therein
31. Y. Minami, C. Kuriyama, K. Ikeda, A. Kato, K. Takebayashi, I. Adachi, W.J.G. Fleet, A. Kettawan, T. Okamoto, and N. Asano Bioorg. Med. Chem. 16 2008 2734
32. S. Ozaki, H. Oe, and S. Kitamura J. Nat. Prod. 71 2008 981
33. H. Oe, and S. Ozaki Biosci. Biotechnol. Biochem. 72 2008 1962
34. G. Tanabe, W. Xie, A. Ogawa, C. Cao, T. Minematsu, M. Yoshikawa, and O. Muraoka Bioorg. Med. Chem. Lett. 19 2009 2195
35. O. Muraoka, W. Xie, G. Tanabe, F.A.M. Amer, T. Minematsu, and M. Yoshikawa Tetrahedron Lett. 49 2008 7315
36. 11h In the present study the reaction time (4 days) and yield (7: revised to be 41%) of the coupling reaction reported have been improved by substituting the reactant from the tosylate to the triflate.
37. L. Wallach, N. Latifeh, and D.T. Scott Carbohydr. Res. 340 2005 1213
38. J. Alais, and A. Veyrieres Carbohydr. Res. 92 1981 310
39. A similar mode of intramolecular cyclization leading to anhydro-sugars has been reported: A.B. Foster, W.G. Overend, M. Stacey, and G. Vaughan J. Chem. Soc. 1954 3367
40. K. Peter, and K. Herbert Liebigs Ann. Chem. 11 1981 1960
41. F. Valentin Collect. Czech. Chem. Commun. 6 1934 354
42. M.L. Wolfrom, P. Chakravarty, and D. Horton J. Org. Chem. 31 1966 2502