C-Aryl glucosides substituted at the 4′-position as potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 15, 2011, Pages 4465-4470

  Xu, Baihua ^a,b   Feng, Yan ^b   Cheng, Huawei ^b   Song, Yanli ^b   Lv, Binhua ^a,b   Wu, Yuelin ^b   Wang, Congna ^b   Li, Shengbin ^b   Xu, Min ^b   Du, Jiyan ^b   Peng, Kun ^b   Dong, Jiajia ^b   Zhang, Wenbin ^b   Zhang, Ting ^b   Zhu, Liangcheng ^b   Ding, Haifeng ^b   Sheng, Zelin ^b   Welihinda, Ajith ^c,d   Roberge, Jacques Y ^b   Seed, Brian ^c   Chen, Yuanwei ^a,b   more..

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Egret Pharma (Shanghai) Limited   (China)

^c Theracos Inc   (United States)

^d Palo Alto Institute of Molecular Medicine   (United States)

Author keywords

C Aryl glucosides; Diabetes; Glucosuria; SGLT2; Sodium dependent glucose co transporter; Type 2 diabetes mellitus

Indexed keywords

ANTIDIABETIC AGENT; GLUCOSIDE; SODIUM GLUCOSE COTRANSPORTER 1; SODIUM GLUCOSE COTRANSPORTER 2; SODIUM GLUCOSE COTRANSPORTER 2 INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO CULTURE; MALE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; RAT;

DIABETES MELLITUS, TYPE 2; GLUCOSIDES; HUMANS; HYPOGLYCEMIC AGENTS; SODIUM-GLUCOSE TRANSPORTER 1; SODIUM-GLUCOSE TRANSPORTER 2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960359068     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.06.032     Document Type: Article

References (30)

1. R.C. Bonadonna Rev. Endocr. Metab. Disord. 5 2004 89
2. D.S. Bell Am. J. Med. 116 2004 23S
3. A. Oku, K. Ueta, K. Arakawa, T. Ishihara, M. Nawano, Y. Kuronuma, M. Matsumoto, A. Saito, K. Tsujihara, M. Anai, T. Asano, Y. Kanai, and H. Endou Diabetes 48 1999 1794
4. K. Tsujihara, M. Hongu, K. Saito, H. Kawanishi, K. Kuriyama, M. Matsumoto, A. Oku, K. Ueta, M. Tsuda, and A. Saito J. Med. Chem. 42 1999 5311
5. K. Arakawa, T. Ishihara, A. Oku, M. Nawano, K. Ueta, K. Kitamura, M. Matsumoto, and A. Saito Br. J. Pharmacol. 132 2001 578
6. M. Isaji Curr. Opin. Invest. Drugs 8 2007 285
7. W.N. Washburn J. Med. Chem. 52 2009 1785
8. W.N. Washburn Expert Opin. Ther. Patents 19 2009 1485
9. K. Katsuno, Y. Fujimori, Y. Takemura, M. Hiratochi, F. Itoh, Y. Komatsu, H. Fujikura, and M. Isaji J. Pharmacol. Exp. Ther. 320 2007 323
10. Y. Fujimori, K. Katsuno, I. Nakashima, Y. Ishikawa-Takemura, H. Fujikura, and M. Isaji J. Pharmacol. Exp. Ther. 327 2008 268
11. W. Meng, B.A. Ellsworth, A.A. Nirschl, P.J. McCann, M. Patel, G. Wu, P.M. Sher, E.P. Morrison, S.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
12. 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
13. B.A. Ellsworth, W. Meng, M. Patel, R.N. Girotra, G. Wu, P.M. Sher, D.L. Hagan, M.T. Obermeier, W.G. Humphreys, J.G. Robertson, A. Wang, S. Han, T.L. Waldron, N.N. Morgan, J.M. Whaley, and W.N. Washburn Bioorg. Med. Chem. Lett. 18 2008 4770
14. B. Xu, B. Lv, Y. Feng, G. Xu, J. Du, A. Welihinda, Z. Sheng, B. Seed, and Y. Chen Bioorg. Med. Chem. Lett. 19 2009 5632
15. B. Lv, B. Xu, Y. Feng, K. Peng, G. Xu, J. Du, L. Zhang, W. Zhang, T. Zhang, L. Zhu, H. Ding, Z. Sheng, A. Welihinda, B. Seed, and Y. Chen Bioorg. Med. Chem. Lett. 19 2009 6877
16. Chen, Y.; Feng, Y.; Xu, B.; Lv, B.; Dong, J.; Seed, B.; Hadd, M. J. PCT Int. Appl. WO2007140191, 2007; Chem. Abstr. 2007, 147, 542063.
17. B. Xu, Y. Feng, B. Lv, G. Xu, L. Zhang, J. Du, K. Peng, M. Xu, J. Dong, W. Zhang, T. Zhang, L. Zhu, H. Ding, Z. Sheng, A. Welihinda, B. Seed, and Y. Chen Bioorg. Med. Chem. 18 2010 4422
18. Ellsworth, B.; Washburn, W. N.; Sher, P. M.; Wu, G.; Meng, W. U. S. Patent, US6414126, 2002.
19. Eckhardt, M.; Eickelmann, P.; Himmelsbach, F.; Barsoumian, E. L.; Leo, T. PCT Int. Appl. WO2005092877, 2005; Chem. Abstr. 2005, 143, 286629.
20. Y. Okimoto, S. Sakaguchi, and Y. Ishii J. Am. Chem. Soc. 124 2002 1590
21. S. Czernecki, and G. Ville J. Org. Chem. 54 1989 610
22. R. Bihovsky, C. Selick, and I. Giusti J. Org. Chem. 53 1988 4026
23. 2,3,4,6-Tetra-O-trimethylsilyl-d-glucolactone was prepared according to the following literature procedures: D. Horton, and W. Priebe Carbohydr. Res. 94 1981 27
24. Deshpande, P. P.; Ellsworth, B. A.; Singh, J.; Denzel, T. W.; Lai, C.; Crispino, G.; Randazzo, M. E.; Gougoutas, J. Z. PCT Int. Appl. WO2004063209, 2004; Chem. Abstr. 2004, 141, 89317.
25. J.M. Lancelin, P.H.A. Zollo, and P. Sinay Tetrahedron Lett. 24 1983 4833
26. The methods for the preparation of the corresponding halides or 4-methylbenzenesulfonates were described in the following patent: Song, Y.; Chen, Y.; Cheng, H.; Li, S.; Wu, Y.; Feng, Y.; Lv, B.; Xu, B.; Seed, B.; Hadd, M. J.; Du, J.; Wang, C.; Roberge, J. Y. PCT Int. Appl. WO2009026537, 2009; Chem. Abstr. 2009, 150, 237833.
27. F. Minisci, F. Recupero, F. Fontana, H.R. Bjørsvik, and L. Liguori Synlett 2002 610
28. Z.Q. Yang, J.C. Lorenz, and Y. Shi Tetrahedron Lett. 39 1998 8621
29. J.C. Lorenz, J. Long, Z.Q. Yang, S. Xue, Y. Xie, and Y. Shi J. Org. Chem. 69 2004 327
30. O.G. Kulinkovich, S.V. Sviridov, and D.A. Vasilevski Synthesis 1991 234