Discovery of novel N -β- d -Xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes

Journal of Medicinal Chemistry

Volumn 54, Issue 1, 2011, Pages 166-178

  Yao, Chun Hsu ^a   Song, Jen Shin ^a   Chen, Chiung Tong ^a   Yeh, Teng Kuang ^a   Hung, Ming Shiu ^a   Chang, Chih Chun ^a   Liu, Yu Wei ^a   Yuan, Mao Chia ^a   Hsieh, Chieh Jui ^a   Huang, Chung Yu ^a   Wang, Min Hsien ^a   Chiu, Ching Hui ^a   Hsieh, Tsung Chih ^a   Wu, Szu Huei ^a   Hsiao, Wen Chi ^a   Chu, Kuang Feng ^a   Tsai, Chi Hui ^a   Chao, Yu Sheng ^a   Lee, Jinq Chyi ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLORO 3 (4 CYCLOPROPYLBENZYL) 1 (BETA DEXTRO XYLOPYRANOSYL) 1H INDOLE; ANTIDIABETIC AGENT; INDOLE DERIVATIVE; PHLORIZIN; SODIUM GLUCOSE COTRANSPORTER 2; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; GLUCOSE URINE LEVEL; HUMAN; HUMAN CELL; HYPERGLYCEMIA; MALE; MOUSE; NONHUMAN; RAT; SINGLE DRUG DOSE; STREPTOZOCIN DIABETES; URINARY EXCRETION;

ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; DIABETES MELLITUS, EXPERIMENTAL; DIABETES MELLITUS, TYPE 2; GLUCOSE; GLUCOSIDES; HUMANS; HYPERGLYCEMIA; HYPOGLYCEMIC AGENTS; INDOLES; MALE; MICE; MICE, INBRED ICR; RATS; RATS, SPRAGUE-DAWLEY; SODIUM-GLUCOSE TRANSPORTER 2; STRUCTURE-ACTIVITY RELATIONSHIP; XYLOSE;

EID: 78651112964     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101072y     Document Type: Article

References (31)

1. Bonadonna, R. C. Alterations of Glucose Metabolism in Type 2 Diabetes Mellitus. An Overview Rev. Endocr. Metab. Disord. 2004, 5, 89-97
2. Klein, R. Hyperglycemia and Microvascular and Macrovascular Disease in Diabetes Diabetes Care 1995, 18, 258-268
3. Libel, A.; Mata, M.; Eschwège, E. Evaluation of Risk Factors for Development of Complications in Type II Diabetes in Europe Diabetologia 2002, 45, S23-S28
4. Saydah, S. H.; Fradkin, J.; Cowie, C. C. Poor Control of Risk Factors for Vascular Disease Among Adults with Previously Diagnosed Diabetes JAMA, J. Am. Med. Assoc. 2004, 291, 335-342
5. +-Glucose Cotransporters Am. J. Physiol.: Renal Physiol. 2001, 280, F10-F18
6. Wright, E. M.; Turk, E. The Sodium/Glucose Cotransport Family SLC5 Pfluegers Arch. 2004, 447, 510-518
7. +-Glucose Cotransporters: SLC5 Physiology 2004, 19, 370-376
8. +/Glucose Cotransporter Nature 1991, 350, 354-356
9. +/Glucose Cotransporter (SGLT1) Trafficking and Function Cause Glucose/Galactose Malabsorption Nat. Genet. 1996, 12, 216-220
10. +/Glucose Cotransporter Gene SGLT1 in a Patient with Congenital Glucose-Galactose Malabsorption: Normal Trafficking but Inactivation of the Mutant Protein Biochim. Biophys. Acta 2001, 1536, 141-147
11. van den Heuvel, L. P.; Assink, K.; Willemsen, M.; Monnens, L. Autosomal Recessive Renal Glucosuria Attributable to a Mutation in the Sodium Glucose Cotransporter (SGLT2) Hum. Genet. 2002, 111, 544-547
12. Magen, D.; Sprecher, E.; Zelikovic, I.; Skorecki, K. A Novel Missense Mutation in SLC5A2 Encoding SGLT2 Underlies Autosomal-Recessive Renal Glucosuria and Aminoaciduria Kidney Int. 2005, 67, 34-41
13. Ehrenkranz, J. R. L.; Lewis, N. G.; Kahn, C. R.; Roth, J. Phlorizin: A Review Diabetes Metab. Res. Rev. 2005, 21, 31-38
14. +-Glucose Cotransporters, May Provide a Novel Approach to Treating Diabetes Diabetes 1999, 48, 1794-1800
15. Katsuno, K.; Fujimori, Y.; Takemura, Y.; Hiratochi, M.; Itoh, F.; Komatsu, Y.; Fujikura, H.; Isaji, M. Sergliflozin, a Novel Selective Inhibitor of Low-Affinity Sodium Glucose Cotransporter (SGLT2), Validates the Critical Role of SGLT2 in Renal Glucose Reabsorption and Modulates Plasma Glucose Level J. Pharmacol. Exp. Ther. 2007, 320, 323-330
16. Fujimori, Y.; Katsuno, K.; Nakashima, I.; Ishikawa-Takemura, Y.; Fujikura, H.; Isaji, M. Remogliflozin Etabonate, in a Novel Category of Selectivelow-Affinity High-Capacity Sodium Glucose Cotransporter (SGLT2) Inhibitors, Exhibits Antidiabetic Efficacy in Rodent Models J. Pharmacol. Exp. Ther. 2008, 327, 268-276
17. Marsenic, O. Glucose Control by the Kidney: An Emerging Target in Diabetes Am. J. Kidney Dis. 2009, 53, 875-883
18. Colca, J. R. Discontinued Drugs in 2008: Endocrine and Metabolic Expert Opin. Invest. Drugs 2009, 18, 1243-1255
19. Kissei Pharmaceutical Co. Ltd. Discontinuation of the Development of "Remogliflozin" by GlaxoSmithKline. News Release, July 3, 2009.
20. Meng, W.; Ellsworth, B. A.; Nirschl, A. A.; McCann, P. J.; Patel, M.; Girotra, R. N.; Wu, G.; Sher, P. M.; Morrison, E. P.; Biller, S. A.; Zahler, R.; Deshpande, P. P.; Pullockaran, A.; Hagan, D. L.; Morgan, N.; Taylor, J. R.; Obermeier, M. T.; Humphreys, W. G.; Khanna, A.; Discenza, L.; Robertson, J. G.; Wang, A.; Han, S.; Wetterau, J. R.; Janovitz, E. B.; Flint, O. P.; Whaley, J. M.; Washburn, W. N. Discovery of Dapagliflozin: A Potent, Selective Renal Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes J. Med. Chem. 2008, 51, 1145-1149
21. Calado, J. Dapagliflozin, an Oral Sodium Glucose Cotransporter Type 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus IDrugs 2009, 12, 785-798
22. Nomura, S.; Sakamaki, S.; Hongu, M.; Kawanishi, E.; Koga, Y.; Sakamoto, T.; Yamamoto, Y.; Ueta, K.; Kimata, H.; Nakayama, K.; Tsuda-Tsukimoto, M. Discovery of Canagliflozin, a Novel C -Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus J. Med. Chem. 2010, 53, 6355-6360
23. Washburn, W. N. Evolution of Sodium Glucose Co-Transporter 2 Inhibitors as Anti-Diabetic Agents Expert Opin. Ther. Pat. 2009, 19, 1485-1499
24. Nomura, S.; Yamamoto, Y. Indole Derivatives. PCT Int. Appl. WO2006080577, 2006.
25. Nomura, S.; Sakamaki, S. Indole Derivatives. PCT Int. Appl. WO2008013322, 2008.
26. Teranishi, H.; Kikuchi, N.; Ohno, K. 1(Beta- d -Glycopyranosyl)-3- Substituted Nitrogenous Heterocyclic Compound, Medicinal Composition Containing the Same, and Medicinal Use Thereof. US20080139484, 2008.
27. Goodwin, N. C.; Mabon, R.; Harrison, B. A.; Shadoan, M. K.; Almstead, Z. Y.; Xie, Y.; Healy, J.; Buhring, L. M.; DaCosta, C. M.; Bardenhagen, J.; Mseeh, F.; Liu, Q.; Nouraldeen, A.; Wilson, A. G. E.; Kimball, S. D.; Powell, D. R.; Rawlins, D. B. Novel l -Xylose Derivatives as Selective Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitors for the Treatment of Type 2 Diabetes J. Med. Chem. 2009, 52, 6201-6204
28. James, P. N.; Snyder, H. R. Indole-3-aldehyde Org. Synth. 1959, 39, 30-32
29. Castaneda, F.; Kinne, R. K.-H. A 96-Well Automated Method To Study Inhibitors of Human Sodium-Dependent d -Glucose Transport Mol. Cell. Biochem. 2005, 280, 91-98
30. +/ d -Glucose Cotransporter (SGLT1) in a Stably Transfected Chinese Hamster Ovary Cell Line Biochim. Biophys. Acta 1998, 1373, 309-320
31. Xu, B.; Feng, Y.; Lv, B.; Xu, G.; Zhang, L.; Du, J.; Peng, K.; Xu, M.; Dong, J.; Zhang, W.; Zhang, T.; Zhu, L.; Ding, H.; Sheng, Z.; Welihinda, A.; Seed, B.; Chen, Y. Bioorg. Med. Chem. 2010, 18, 4422-4432