Design, synthesis, and pharmacological evaluation of N-(4-mono and 4,5-disubstituted thiazol-2-yl)-2-aryl-3-(tetrahydro-2H-pyran-4-yl)propanamides as glucokinase activators

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 11, 2010, Pages 3875-3884

  Li, Fuying ^a   Zhu, Qingzhang ^a   Zhang, Yi ^a   Feng, Ying ^a   Leng, Ying ^a   Zhang, Ao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Aminothiazole; Arylacetamide; Glucokinase activator; Type 2 diabetes (T2D)

Indexed keywords

2 (4 (CYCLOPROPYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL) N (4,5,6,7 TETRAHYDROBENZO[D]THIAZOL 2 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (4 (PROP 1 EN 2 YL)THIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (4 ISOPROPYLTHIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (4 OXO 4,5 DIHYDROTHIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (5 (2 METHYLPROPYLIDENE) 4 OXO 4,5 DIHYDRO THIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (5 IODO 4 ISOPROPYLHIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (5 METHYL 4,5,6,7 TETRAHYDROTHIAZOLO[5,4 C] PYRIDIN 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) N (5,6 DIHYDRO 4H CYCLOPENTA[D]THIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; 2 (4 (METHYLSULFONYL)PHENYL) N (4 PHENYLTHIAZOL 2 YL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; ANTIDIABETIC AGENT; GLUCOSE; N (4 (4 FLUOROPHENYL)THIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (4 (4 METHOXYPHENYL)THIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (4 CYCLOPROPYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (4 ETHYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL) PROPANAMIDE; N (4 ISOBUTYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL) PROPANAMIDE; N (4 ISOPROPYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL) PROPANAMIDE; N (4 TERT BUTYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL) PROPANAMIDE; N (4,5 DIMETHYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (5 BENZYLIDENE 4 OXO 4,5 DIHYDROTHIAZOL 2 YL) 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (5 BROMO 4 ISOPROPYLTHIAZOL 2 YL) 2 (4 (CYCLOPROPYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (5 ISOPROPYL 4 METHYLTHIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; N (6 FLUOROBENZO[D]THIAZOL 2 YL) 2 (4 (METHYLSULFONYL)PHENYL) 3 (TETRAHYDRO 2H PYRAN 4 YL)PROPANAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL CELL CULTURE; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVATION; FEMALE; GLUCOSE BLOOD LEVEL; GLUCOSE TRANSPORT; GLYCEMIC CONTROL; GLYCOGEN SYNTHESIS; LIVER CELL; MALE; MOUSE; NONHUMAN; RAT; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

ACETAMIDES; ADMINISTRATION, ORAL; ANIMALS; BLOOD GLUCOSE; DIABETES MELLITUS, TYPE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; GLUCOKINASE; GLUCOSE; GLYCOSIDE HYDROLASES; HEPATOCYTES; HYPOGLYCEMIC AGENTS; MICE; MICE, INBRED STRAINS; RATS; THIAZOLES;

MUS; RATTUS;

EID: 77953131053     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.04.038     Document Type: Article

References (46)

1. Smith J.P. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 13225
2. Xuan S., Kitamura T., Nakae J., Politi K., Kido Y., Fisher P.E., Morroni M., Cinti S., White M.F., Herrera P.L., Accili D., and Efstratiadis A. J. Clin. Invest. 110 (2002) 1011
3. Reaven G.M. Physiol. Rev. 75 (1995) 473
4. Reaven G., Abbasi F., and McLaughlin T. Recent Prog. Horm. Res. 59 (2004) 207
5. de Luca C., and Olefsky J.M. FEBS Lett. 582 (2008) 97
6. Ader M., Ni T.C., and Bergman R.N. J. Clin. Invest. 99 (1997) 1187
7. Tenenbaum A., Motro M., and Schwammenthal E. Int. J. Cardiol. 97 (2004) 167
8. Gershell L. Nat. Rev. Drug Disc. 4 (2005) 367
9. Nathan D.M. N. Engl. J. Med. 347 (2002) 1342
10. Cárdenas M.L. Glucokinase: Its Regulation and Role in Liver Metabolism. R. G. Landes Co, Austin, 1995.
11. Matschinsky F.M. Diabetes 45 (1996) 223
12. Matschinsky F.M., and Ellerman J.E. J. Biol. Chem. 243 (1968) 2730
13. Gloyn A.L., Odili S., Buettger C., Njolstad P.R., Chiyo C., Magnuson M.A., and Matschinsky F.M. In: Matschinksy F.M., and Magnuson M.A. (Eds). Glucokinase and Glycemic Disease: From Basics to Novel Therapeutics (2004), Karger, Basel 92-109
14. Van Schaftingen E. Diabetologia 37 (1994) S43
15. Farrelly D., Brown K.S., Tieman A., Ren J., Lira S.A., Hagan D., Gregg R., Mookhtiar K.A., and Hariharan N. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 14511
16. Ferris S.A. Metabolism 13 (1964) 1478
17. Basu A., Basu R., Shah P., Vella A., Johnson C.M., Nair K.S., Jensen M.D., Schwenk W.F., and Rizza R.A. Diabetes 49 (2000) 272
18. Hawkins M., Gabriely I., Wozniak R., Vilcu C., Shamoon H., and Rossetti L. Diabetes 51 (2002) 606
19. Agius L. Biochem. J. 414 (2008) 1
20. Grimsby J., Sarabu R., Corbett W.L., Haynes N.-E., Bizzarro F.T., Coffey J.W., Guertin K.R., Hilliard D.W., Kester R.F., Mahaney P.E., Marcus L., Qi L., Spence C.L., Tengi J., Magnuson M.A., Chu C.A., Dvorozniak M.T., Matschinsky F.M., and Grippo J.F. Science 301 (2003) 370
21. Efanov A.M., Barrett D.G., Brenner M.B., Briggs S.L., Delaunois A., Durbin J.D., Giese U., Guo H., Radloff M., Gil G.S., Sewing S., Wang Y., Weichert A., Zaliani A., and Gromada J. Endocrinology 146 (2005) 3696
22. Sarabu R., and Tilley J. Annu. Rep. Med. Chem. 40 (2005) 167
23. Sarabu R., and Grimsby J. Curr. Opin. Drug Discov. Devel. 8 (2005) 631
24. Johnson T.O., and Humphries P.S. Annu. Rep. Med. Chem. 41 (2006) 141
25. Guertin K.R., and Grimsby J. Curr. Med. Chem. 13 (2006) 1839
26. Fyfe M.C.T., White J., Taylor A., Chatfield R., Wargent E., Printz R.L., Sulpice T., McCormack J.G., Procter M.J., Reynet C., Widdowson P.S., and Wong-kai-in P. Diabetologia 50 (2007) 1277
27. Coghlan M., and Leighton B. Expert Opin. Investig. Drugs 17 (2008) 145
28. Grimsby J., Berthel S.J., and Sarabu R. Curr. Top. Med. Chem. 8 (2008) 1524
29. Sarabu R., Berthel S.J., Kester R.F.K., and Tilley J.W.T. Expert Opin. Ther. Pat. 18 (2008) 759
30. Matschinsky F.M. Nat. Rev. Drug Disc. 8 (2009) 399
31. Pal M. Curr. Med. Chem. 16 (2009) 3858
32. Pal M. Drug Discovery Today 14 (2009) 784
33. Bertram L.S., Black D., Briner P.H., Chatfield R., Cooke A., Fyfe M.C., Murray P.J., Naud F., Nawano M., Procter M.J., Rakipovski G., Rasamison C.M., Reynet C., Schofield K.L., Shah V.K., Spindler F., Taylor A., Turton R., Williams G.M., Wong-Kai-In P., and Yasuda K. J. Med. Chem. 51 (2008) 4340
34. Bebernitz G.R., Beaulieu V., Dale B.A., Deacon R., Duttaroy A., Gao J., Grondine M.S., Gupta R.C., Kakmak M., Kavana M., Kirman L.C., Liang J., Maniara W.M., Munshi S., Nadkarni S.S., Schuster H.F., Stams T., Denny I.S., Taslimi P.M., Vash B., and Caplan S.L. J. Med. Chem. 52 (2009) 6142
35. McKerrecher D., Allen J.V., Bowker S.S., Boyd S., Caulkett P.W., Currie G.S., Davies C.D., Fenwick M.L., Gaskin H., Grange E., Hargreaves R.B., Hayter B.R., James R., Johnson K.M., Johnstone C., Jones C.D., Lackie S., Rayner J.W., and Walker R.P. Bioorg. Med. Chem. Lett. 15 (2005) 2103
36. McKerrecher D., Allen J.V., Caulkett P.W., Donald C.S., Fenwick M.L., Grange E., Johnson K.M., Johnstone C., Jones C.D., Pike K.G., Rayner J.W., and Walker R.P. Bioorg. Med. Chem. Lett. 16 (2006) 2705
37. Johnson D., Shepherd R.M., Gill D., Gorman T., Smith D.M., and Dunne M.J. Diabetes 56 (2007) 1694
38. Briner, P. H.; Fyfe, M. C. T.; Madeley, J. P.; Murray, P. J.; Procter, M. J.; Spindler, F. World Patent Application No. WO 2006/016178.
39. In: Dunten P., Swain A., Kammlott U., Crowther R., Lukacs C.M., Levin W., Reik L., Grimsby J., Corbett W.L., Magnuson M.A., Matschinsky F.M., Matschinsky F.M., and Magnuson M.A. (Eds). Glucokinase and Glycemic Disease: From Basics to Novel Therapeutics (2004), Karger, Basel 145-154
40. Zhang Y., Han Z., Li F., Ding K.-L., and Zhang A. Chem. Commun. 46 (2010) 156
41. Luo Y., Ma L., Zheng H., Chen L., Li R., He C., Yang S., Ye X., Chen Z., Li Z., Gao Y., Han J., He G., Yang L., and Wei Y. J. Med. Chem. 53 (2010) 273
42. Zhang L., Li H., Zhu Q., Liu J., Chen L., Leng Y., Jiang H., and Liu H. Bioorg. Med. Chem. 17 (2009) 7301
43. Brocklehurst K.J., Payne V.A., Davies R.A., Carroll D., Vertigan H.L., Wightman H.J., Aiston S., Waddell I.D., Leighton B., Coghlan M.P., and Agius L. Diabetes 53 (2004) 535
44. Yang R., Cao L., Gasa R., Brady M.J., Sherry A.D., and Newgard C.B. J. Biol. Chem. 277 (2002) 1514
45. Keppler D., and Decker K. Glycogen. In: Bergmeyer H.U., Grassl M., and Bergmeyer J. (Eds). Methods of Enzymatic Analysis: Metabolites 1. 3rd ed. (1984), Weinheim, Verlag chemie 11-14
46. Otto M., Breinholt J., and Westergaard N. Diabetes Obes. Metab. 5 (2003) 189