Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110α inhibitors

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 17, 2007, Pages 5837-5844

  Hayakawa, Masahiko ^a   Kawaguchi, Ken ichi ^a   Kaizawa, Hiroyuki ^a   Koizumi, Tomonobu ^a   Ohishi, Takahide ^a   Yamano, Mayumi ^a   Okada, Minoru ^a   Ohta, Mitsuaki ^a   Tsukamoto, Shin ichi ^a   Raynaud, Florence I ^b   Parker, Peter ^c   Workman, Paul ^b   Waterfield, Michael D ^d  

^a ASTELLAS PHARMA INC   (Japan)

^b INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^c IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

^d LUDWIG INSTITUTE FOR CANCER RESEARCH   (United Kingdom)

Author keywords

Anti cancer agent; Inhibitor; p110 ; PI3 kinase

Indexed keywords

ANTINEOPLASTIC AGENT; HYDRAZONE DERIVATIVE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; IMIDAZOPYRIDINE DERIVATIVE; N' [(6 BROMOIMIDAZO[1,2 A]PYRIDIN 3 YL)METHYLENE] 2 METHYL 5 NITROBENZENESULFONOHYDRAZIDE; N' [(6 BROMOIMIDAZO[1,2 A]PYRIDIN 3 YL)METHYLENE] N,2 DIMETHYL 5 NITROBENZENESULFONOHYDRAZIDE; N' [(6 CYANOIMIDAZO[1,2 A]PYRIDIN 3 YL)METHYLENE] N,2 DIMETHYL 5 NITROBENZENESULFONOHYDRAZIDE; N' [1 (6 BROMO 2 METHYLIMIDAZO[1,2 A]PYRIDIN 3 YL)ETHYLIDENE] 2 METHYL 5 NITROBENZENESULFONOHYDRAZIDE; PHOSPHATIDYLINOSITOL 3 KINASE INHIBITOR; PROTEIN; PROTEIN P110ALPHA; PROTEIN P110ALPHA INHIBITOR; PYRAZOLE; REAGENT; SOLVENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; CELL PROLIFERATION; DRUG EFFICACY; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; SUBSTITUTION REACTION; TUMOR CELL;

1-PHOSPHATIDYLINOSITOL 3-KINASE; ANIMALS; CELL LINE, TUMOR; CELL PROLIFERATION; ENZYME ACTIVATION; HUMANS; HYDRAZONES; IMIDAZOLES; INHIBITORY CONCENTRATION 50; ISOENZYMES; MICE; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PROTEIN SUBUNITS; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR; TEMPERATURE; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 34447254744     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.070     Document Type: Article

References (22)

1. Ward S., Sotsios Y., Dowden J., Bruce I., and Finan P. Chem. Biol. 10 (2003) 207
2. Ward S.G., and Finan P. Curr. Opin. Pharmacol. 3 (2003) 426
3. Workman P. Biochem. Soc. Trans. 32 (2004) 393
4. Hopkins K. Science 282 (1998) 1027
5. Maehama T., and Dixon J.E. Trends Cell Biol. 9 (1999) 125
6. Simpson L., and Parsons R. Exp. Cell Res. 264 (2001) 29
7. Vanhaesebroeck B., Leevers S.J., Ahmadi K., Timms J., Katso R., Driscoll P.C., Woscholski R., Parker P.J., and Waterfield M.D. Annu. Rev. Biochem. 70 (2001) 535
8. Cantley L.C. Science 296 (2002) 1655
9. Lawlor M.A., and Alessi D.R. J. Cell Sci. 114 (2001) 2903
10. Domin J., and Waterfield M.D. FEBS Lett. 410 (1997) 91
11. Shayesteh L., Lu Y., Kuo W.-L., Baldocchi R., Godfrey T., Collins C., Pinkel D., Powell B., Mills G.B., and Gray J.W. Nat. Genet. 21 (1999) 99
12. Ma Y.-Y., Wei S.-J., Lin Y.-C., Lung J.-C., Chang T.-C., Whang-Peng J., Liu J.M., Yang D.-M., Yang W.K., and Schen C.-Y. Oncogene 19 (2000) 2739
13. Samuels Y., Wang Z., Bardelli A., Silliman N., Ptak J., Szabo S., Yan H., Gazdar A., Powell S.M., Riggins G.J., Willson J.K., Markowitz S., Kinzler K.W., Vogelstein B., and Velculescu V.E. Science 304 (2004) 554
14. Campbell I.G., Russell S.E., Choong D.Y., Montgomery K.G., Ciavarella M.L., Hooi C.S., Cristiano B.E., Pearson R.B., and Phillips W.A. Cancer Res. 64 (2004) 7678
15. Kang S., Bader A.G., and Vogt P.K. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 802
16. Parsons D.W., Wang T.-L., Samuels Y., Bardelli A., Cummins J.M., DeLong L., Silliman N., Ptak J., Szabo S., Willson J.K., Markowitz S., Kinzler K.W., Vogelstein B., Lengauer C., and Velculescu V.E. Nature 436 (2005) 792
17. Hayakawa M., Kaizawa H., Moritomo H., Koizumi T., Ohishi T., Okada M., Ohta M., Tsukamoto S., Parker P., Workman P., and Waterfield M. Bioorg. Med. Chem. 14 (2006) 6847
18. Hayakawa M., Kaizawa H., Kawaguchi K., Ishikawa N., Koizumi T., Ohishi T., Yamano M., Okada M., Ohta M., Tsukamoto S., Raynaud F.I., Waterfield M.D., Parker P., and Workman P. Bioorg. Med. Chem. 15 (2007) 403
19. Hayakawa M., Kaizawa H., Moritomo H., Koizumi T., Ohishi T., Yamano M., Okada M., Ohta M., Tsukamoto S., Raynaud F.I., Workman P., Waterfield M.D., and Parker P. Bioorg. Med. Chem. Lett. 17 (2007) 2438
20. Knight Z.A., Gonzalez B., Feldman M.E., Zunder E.R., Goldenberg D.D., Williams O., Loewith R., Stokoe D., Balla A., Toth B., Balla T., Weiss W.A., Williams R.L., and Shokat K.M. Cell 125 (2006) 733
21. Fairchild C.R., Ivy S.P., Kao-Shan C.-S., Whang-Peng J., Rosen N., Israel M.A., Melera P.W., Cowan K.H., and Goldsmith M.E. Cancer Res. 47 (1987) 5141
22. Scudiero D.A., Monks A., and Sausville E.A. J. Natl. Cancer Inst. 90 (1998) 862