Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 13, 2006, Pages 4490-4518

  Charton, Julie ^a   Girault Mizzi, Sophie ^a   Debreu Fontaine, Marie Ange ^a   Foufelle, Fabienne ^b   Hainault, Isabelle ^b   Bizot Espiard, Jean Guy ^c   Caignard, Daniel Henri ^c   Sergheraert, Christian ^a  

^a CNRS   (France)

^b INSERM   (France)

^c INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

AMP activated protein kinase; Benzimidazole derivatives

Indexed keywords

2 (1 PHENYLCYCLOPENTYL) 1H BENZOIMIDAZOLE; 2 (1 PHENYLETHYL) 1H BENZOIMIDAZOLE; 2 (1 PHENYLHEPTYL) 1H BENZOIMIDAZOLE; 2 (1 PHENYLPROPYL) 1H BENZOIMIDAZOLE; 2 (1,2,3,4 TETRAHYDRONAPHTHALEN 2 YL) 1H BENZOIMIDAZOLE; 2 (1H INDOL 3 YLMETHYL) 1H BENZOIMIDAZOLE; 2 (2 FURAN 2 YLPHENYL) 1H BENZOIMIDAZOLE; 2 (2 IODOPHENYL) 1H BENZOIMIDAZOLE; 2 (2 PHENYLCYCLOPROPYL) 1H BENZOIMIDAZOLE; 2 (2 PHENYLPROPYL) 1H BENZOIMIDAZOLE; 2 (4 PROPYLPHENYL) 1H BENZOIMIDAZOLE; 2 (9H FLUOREN 9 YL) IH BENZOIMIDAZOLE; 2 (CYCLOHEXYLPHENYLMETHYL) 1H BENZOIMIDAZOLE; 2 (CYCLOPENTYLPHENYLMETHYL) 1H BENZOIMIDAZOLE; 2 BENZHYDRYL 1H BENZOIMIDAZOLE; 2 BENZO[B]THIOPEN 3 YLMETHYL 1H BENZOIMIDAZOLE; 2 BENZYL 1H BENZOIMIDAZOLE; 2 BIPHENYL 2 YL 1H BENZOIMIDAZOLE; 2 BIPHENYL 3 YL 1H BENZOIMIDAZOLE; 2 BIPHENYL 4 YL 1H BENZOIMIDAZOLE; 2 CYCLOHEXYLMETHYL 1H BENZOIMIDAZOLE; 2 DICYCLOHEXYLMETHYL 1H BENZOIMIDAZOLE; 2 NAPHTHALEN 1 YLMETHYL 1H BENZOIMIDAZOLE; 2 NAPHTHALEN 2 YLMETHYL 1H BENZOIMIDAZOLE; 2 PHENYL 1H BENZOIMIDAZOLE; 2 PIPERIDIN 1H BENZOIMIDAZOLE; ADENYLATE KINASE; BENZIMIDAZOLE DERIVATIVE; PROTEIN KINASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENERGY BALANCE; ENERGY METABOLISM; ENZYME ACTIVATION; EVALUATION; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZIMIDAZOLES; BIOLOGICAL ASSAY; CYCLOHEXANES; ENERGY METABOLISM; FEMALE; MULTIENZYME COMPLEXES; PROTEIN-SERINE-THREONINE KINASES; RATS; RATS, WISTAR;

EID: 33646560007     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.02.028     Document Type: Article

References (26)

1. Winder W.W., and Hardie D.G. Am. J. Physiol. 277 (1999) 1-10
2. Moller D.E. Nature 414 (2001) 821-827
3. Minokoshi Y., Kim Y.B., Peroni O.D., Fryer L.G., Muller C., Carling D., and Kahn B.B. Nature 415 (2002) 339-343
4. Ruderman N., and Pentki M. Nat. Rev. Drug Discov. 3 (2004) 340-351
5. Corton J.M., Gillespie J.G., and Hardie D.G. Curr. Biol. 4 (1994) 315-324
6. Hardie D.G., Salt I.P., Hawley S.A., and Davies S.P. Biochem. J. 338 (1999) 717-722
7. Zhou G., Myers R., Li Y., Chen Y., Shen X., Fenyk-Melody J., Wu M., Ventre J., Doebber T., Fujii N., Musi N., Hirshman M.F., Goodyear L.J., and Moller D.E. J. Clin. Invest. 108 (2001) 1167-1174
8. Fryer L.G., Parbu-Patel A., and Carling D. J. Biol. Chem. 277 (2002) 25226-25232
9. Hardie D.G., and Carling D. Eur. J. Biochem. 246 (1997) 259-273
10. Hardie D.G., Scott J.W., Pan D.A., and Hudso E.R. FEBS Lett. 546 (2003) 113-120
11. Kemp B.E., Mitchelhill K.I., Stapleton D., Michell B.J., Chen Z.P., and Witters L.A. Trends Biochem. Sci. 24 (1999) 22-25
12. Sullivan J.E., Brocklehurst K.J., Marley A.E., Carey F., Carling D., and Berimm R.K. FEBS Lett. 353 (1994) 33-36
13. Corton J.M., Gillespie J.G., Hawley S.A., and Hardie D.G. Eur. J. Biochem. 229 (1995) 558-565
14. Charton J., Girault-Mizzi S., and Sergheraert C. Chem. Pharm. Bull. 53 (2005) 492-497
15. Frérot E., Coste J., Panatloni A., Dufour M.N., and Jouin P. Tetrahedron 47 (1991) 259-270
16. Roth T., Morningstar M.L., Boyer P.L., Hughes S.H., Buckheit Jr. R.W., and Michejda C.J. J. Med. Chem. 40 (1997) 4199-4207
17. DeLuca M.R., and Kerwin S.M. Tetrahedron 53 (1997) 457-464
18. Peyman A., Gourvest J.F., Gadek T.R., and Knolle J. Angew. Chem. Int. Ed. 39 (2000) 2874-2877
19. DeLuca M.R., Taraporewala I.B., and Kerwin S.M. Heterocycles 51 (1999) 979-982
20. Sekiya T., Inoue S., Shirasaka T., Miyajima C., Okushima H., Suzuki K., Kawai, Mitsuka M., and Umezu K. Chem. Pharm. Bull. 42 (1994) 586-591
21. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550-9561
22. Ji Y.H., Bur D., Häsler W., Runtz Schmitt V., Dorn A., Bailly C., Waring M.J., Hochstrasser R., and Leupin W. Bioorg. Med. Chem. 9 (2001) 2905-2919
23. Foretz M., Carling D., Guichard C., Ferre' P., and Foufelle F. J. Biol Chem. 273 (1998) 14767-14771
24. Berry M.N., and Friend D.S. J. Cell Biol. 43 (1969) 506-520
25. Berry M.N., and Friend D.S. J. Cell Biol. 43 (1969) 506-520
26. Indirect activation could be the result of ATP synthesis blockade or elevation of ATP consumption.