Synthesis and biological evaluation of α-1-C-4′-arylbutyl-l- arabinoiminofuranoses, a new class of α-glucosidase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 15, 2014, Pages 3298-3301

  Natori, Yoshihiro ^a   Sakuma, Toshihiro ^a   Yoshimura, Yuichi ^a   Kinami, Kyoko ^b   Hirokami, Yuki ^b   Sato, Kasumi ^b   Adachi, Isao ^b   Kato, Atsushi ^b   Takahata, Hiroki ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

1 C 4 Arylbutyl l arabinoiminofuranoses; Iminosugars; Structure activity relationship; Type 2 diabetes; Glucosidase inhibitor

Indexed keywords

ACARBOSE; ALPHA 1 C 4' ARYLBUTYL LEVO ARABINOIMINOFURANOSE; ALPHA 1 C 4' PHENYLBUTYL LEVO ARABINOIMINOFURANOSE; ALPHA 1 C BUTYL LEVO ARABINOIMINOFURANOSE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; IMINOSUGAR; MIGLITOL; OLIGO 1,6 GLUCOSIDASE; SUCRASE; UNCLASSIFIED DRUG; VOGLIBOSE; ALPHA 1 C 4' ARYLBUTYL LEVO ARABINOIMINOFURANOSE DERIVATIVE; FUNCTIONAL GROUP; PHENYL GROUP; 1-(4-(3,5-DIFLUOROPHENYL)BUTYL)IMINOFURANOSE; GLYCOSIDASE INHIBITOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG SYNTHESIS; ENZYME INHIBITION; HYPERGLYCEMIA; IC 50; INTESTINE ABSORPTION; INTESTINE BRUSH BORDER MEMBRANE; MALE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; POSTPRANDIAL STATE; RAT; RING CLOSING METATHESIS; SMALL INTESTINE; STRUCTURE ACTIVITY RELATION; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ENZYMOLOGY; HUMAN; INTESTINE; METABOLISM; SYNTHESIS;

ALPHA-GLUCOSIDASES; DOSE-RESPONSE RELATIONSHIP, DRUG; GLYCOSIDE HYDROLASE INHIBITORS; HUMANS; IMINO SUGARS; INTESTINES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84904070409     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.06.001     Document Type: Article

References (20)

1. P. Compain, and O.R. Martin Iminosugars - From Synthesis to Therapeutic Applications 2007 John Wiley & Sons Ltd. West Sussex, England
2. N. Asano, K. Oseki, E. Tomioka, H. Kizu, and K. Matsui Carbohydr. Res. 259 1994 243
3. R.J. Nash, A. Kato, C.-Y. Yu, and G.W.J. Fleet Future Med. Chem. 3 2011 1513
4. G. Horne, and F.X. Wilson Prog. Med. Chem. 50 2011 135
5. J. Putter E. Brodech, Enzyme Inhibitors 1980 Chemie Weinheim, Germany 139
6. R.R. Holmn, C.A. Cull, and R.C. Turner Diabetes Care 22 1999 960
7. M. Carrascosa, F. Pascual, and S. Aresti Lancet 349 1997 698
8. P.H. Joubert, H.L. Venter, and G.N. Foukaridis Br. J. Clin. Pharmacol. 30 1990 391
9. H. Bischoff Eur. J. Clin. Invest. 24 1994 3
10. A.J. Reuser, and H.A. Wisselaar Eur. J. Clin. Invest. 24 1994 19
11. N. Asano, K. Ikeda, L. Yu, A. Kato, K. Takebayashi, I. Adachi, I. Kato, H. Ouchi, H. Takahata, and G.W.J. Fleet Tetrahedron: Asymmetry 16 2005 223
12. A. Kato, N. Kato, E. Kano, I. Adachi, K. Ikeda, L. Yu, T. Okamoto, Y. Banba, H. Ouchi, H. Takahata, and N. Asano J. Med. Chem. 48 2005 2036
13. H. Ouchi, Y. Mihara, and H. Takahata J. Org. Chem. 70 2005 5207
14. A. Kato, S. Miyauchi, N. Kato, R.J. Nash, Y. Yoshimura, I. Nakagome, S. Hirono, H. Takahata, and I. Adachi Bioorg. Med. Chem. 19 2011 3558
15. A. Kato, E. Hayashi, S. Miyauchi, I. Adachi, T. Imahori, Y. Natori, Y. Yoshimura, R.J. Nash, H. Shimaoka, I. Nakagome, J. Koseki, S. Hirono, and H. Takahata J. Med. Chem. 55 2012 10347
16. Y. Natori, T. Imahori, K. Murakami, Y. Yoshimura, S. Nakagawa, A. Kato, I. Adachi, and H. Takahata Bioorg. Med. Chem. Lett. 21 2011 738
17. B.M. Trost, D.B. Horne, and M.J. Woltering Chem. Eur. J. 12 2006 6607
18. G.C. Fu, and J.S. Zhou J. Am. Chem. Soc. 125 2003 14726
19. W. Puls, U. Keup, H.P. Krause, G. Thomas, and F. Hoffmeister Naturwissenschaften 64 1977 536
20. M. Kessler, O. Acuto, C. Strelli, H. Murer, and G.A. Semenza Biochem. Biophys. Acta 506 1978 136