Exploration of SAR regarding glucose moiety in novel C-aryl glucoside inhibitors of SGLT2

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 2, 2011, Pages 742-746

  Park, Eun Jung ^a   Kong, Younggyu ^a   Lee, Jun Sung ^a   Lee, Sung Han ^a   Lee, Jinhwa ^a  

^a Green Cross Company   (South Korea)

Author keywords

Dapagliflozin; Diabetes; Glucose; SGLT; Thiazole

Indexed keywords

ANTIDIABETIC AGENT; C ARYL GLUCOSIDE DERIVATIVE; DAPAGLIFLOZIN; SODIUM GLUCOSE COTRANSPORTER; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; STRUCTURE ACTIVITY RELATION;

DIABETES MELLITUS; GLYCOSIDES; HUMANS; HYPOGLYCEMIC AGENTS; SODIUM-GLUCOSE TRANSPORTER 2; THIAZOLES;

EID: 78651228778     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.11.115     Document Type: Article

References (28)

1. International Diabetes Federation Diabetes Atlas 4th ed. 2009 International Diabetes Federation Montreal, Canada
2. A. Dwarakanathan J. Insur. Med. 38 2006 20
3. B. Mackenzie, and D.D. Loo J. Biol. Chem. 20 1996 32678
4. O.W. Moe, C.A. Berry, and F.C. Rector B.M. Brenner, F.C. Rector, The Kidney 5th ed. 2000 WB Saunders Co. Philadelphia 375
5. B.A. Ellsworth, W. Meng, M. Patel, R.N. Girotra, G. Wu, P. Sher, D. Hagan, M. Obermeier, W.G. Humphreys, J.G. Robertson, A. Wang, S. Han, T. Waldron, N.N. Morgan, J.M. Whaley, and W.N. Washburn Bioorg. Med. Chem. Lett. 18 2008 4770
6. W. Meng, B.A. Ellsworth, A.A. Nirschl, P.J. McCann, M. Patel, R.N. Girotra, G. Wu, P.M. Sher, E.P. Morrison, A.A. Biller, R. Zahler, P.P. Deshpande, A. Pullockaran, D.L. Hagan, N. Morgan, J.R. Taylor, M.T. Obermeier, W.G. Humphreys, A. Khanna, L. Discenza, J.G. Robertson, A. Wang, S. Han, J.R. Wetterau, E.B. Janovitz, O.P. Flint, J.M. Whaley, and W.N. Washburn J. Med. Chem. 51 2008 1145
7. W.N. Washburn J. Med. Chem. 52 2009 1785
8. According to a report from Business Wire on June 26, 2010, dapagliflozin as add on therapy to insulin demonstrated improved glycemic control in patients with type 2 diabetes inadequately controlled with insulin.
9. S. Nomura, S. Sakamaki, M. Hongu, E. Kawanshi, Y. Koga, T. Sakamoto, Y. Yamamoto, K. Ueta, H. Kimata, K. Nakayama, and M. Tsuda-Tsukimoto J. Med. Chem. 53 2010 6355
10. Lexicon Pharmaceuticals, www.clinicaltrials.gov, 2009, NCT00962065.
11. Mascitti, V. Presented at the 240th American Chemical Society National Meeting and Exposition, Boston, MA, August 2010; CARB 90.
12. J. Lee, S.-H. Lee, H.J. Seo, E.-J. Son, S.H. Lee, M.E. Jung, M. Lee, H.-K. Han, J. Kim, J. Kang, and J. Lee Bioorg. Med. Chem. 18 2010 2178
13. M.J. Kim, J. Lee, S.Y. Kang, S.-H. Lee, E.-J. Son, M.E. Jung, S.H. Lee, K.-S. Song, M. Lee, H.-K. Han, J. Kim, and J. Lee Bioorg. Med. Chem. Lett. 20 2010 3420
14. S.Y. Kang, K.-S. Song, J. Lee, S.-H. Lee, and J. Lee Bioorg. Med. Chem. 18 2010 6069
15. J. Lee, J.Y. Kim, J. Choi, S.-H. Lee, J. Kim, and J. Lee Bioorg. Med. Chem. Lett. 20 2010 7046
16. Song, K.-S.; Lee, S. H.; Kim, M.; Seo, H.; Lee, J.; Lee, S.-H.; Jung, M. E.; Son, E. J.; Lee, M.; Kim, J.; Lee, J. ACS Med. Chem. Lett. doi:10.1021/ml100256c.
17. Modifications at other positions on glucose including C-2, C-3, C-4, and C-5 appear to devastate in vitro inhibitory activity against hSGLT2. See: W.N. Washbrun Exp. Opin. Ther. Patents 19 2009 1485
18. Honda, T.; Oguchi, M.; Yoshida, M.; Okuyama, R.; Ogata, T. Abe, M.; Ueda, K.; Ohsumi, J.; Izumi, M. Patent EP2048105; 2009.
19. W.R. Kobertz, C.R. Bertozzi, and M.D. Bednarski J. Org. Chem. 61 1996 1894
20. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
21. D.M. Walba, H.A. Razavi, and N.A. Clark J. Am. Chem. Soc. 110 1988 8686
22. A. Wolan, and Y. Six Tetrahedron 66 2010 3097
23. J. Lee, C.H. Kang, H. Kim, and J.K. Cha J. Am. Chem. Soc. 118 1996 291
24. S. Hanessian, B.D. Simard, and D. Simard Tetrahedron 65 2009 6656
25. 14C-AMG) uptake assay.
26. 20,21
27. S. Han, D.L. Hagan, J.R. Taylor, L. Xin, W. Meng, S.A. Biller, J.R. Wetterau, W.N. Washburn, and J.M. Whaley Diabetes 57 2008 1723
28. K. Katsuno, Y. Fujimori, Y. Takemura, M. Hiratochi, F. Itoh, Y. Komatsu, H. Fujikura, and M. Isaji J. Pharmacol. Exp. Ther. 320 2007 323