Novel 9-oxo-thiazolo[5,4-f]quinazoline-2-carbonitrile derivatives as dual cyclin-dependent kinase 1 (CDK1)/glycogen synthase kinase-3 (GSK-3) inhibitors: Synthesis, biological evaluation and molecular modeling studies

European Journal of Medicinal Chemistry

Volumn 43, Issue 7, 2008, Pages 1469-1477

  Logé, Cédric ^a   Testard, Alexandra ^b   Thiéry, Valérie ^b   Lozach, Olivier ^c   Blairvacq, Mélina ^c   Robert, Jean Michel ^a   Meijer, Laurent ^c   Besson, Thierry ^b  

^a UNIVERSITÉ DE NANTES   (France)

^b FRE CNRS 2766   (France)

^c STATION BIOLOGIQUE DE ROSCOFF   (France)

Author keywords

CDK1 inhibitor; GSK 3 inhibitor; Microwave assisted chemistry; Molecular modeling; Quinazolinones

Indexed keywords

9 OXO THIAZOLO[5,4 F]QUINAZOLINE 2 CARBONITRILE DERIVATIVE; AMIDINE; CYANIDE; CYCLIN DEPENDENT KINASE 1 INHIBITOR; ENZYME INHIBITOR; GLYCOGEN SYNTHASE KINASE 3 INHIBITOR;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

CDC2 PROTEIN KINASE; ENZYME INHIBITORS; GLYCOGEN SYNTHASE KINASE 3; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NITRILES; QUINAZOLINES; SPECTROPHOTOMETRY, INFRARED;

EID: 45949085044     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.09.020     Document Type: Article

References (23)

1. Manning G., Whyte D.B., Martinez R., Hunter T., and Sudarsanam S. Science 298 (2002) 1912-1934
2. Knockaert M., Greengard P., and Meijer L. Trends Pharmacol. Sci. 23 (2002) 417-425
3. Malumbres M., and Barbacid M. Trends Biochem. Sci. 30 (2005) 630-641
4. Meijer L., Flajolet M., and Greengard P. Trends Pharmacol. Sci. 25 (2004) 471-480
5. Jope R.S., and Johnson G.V. Trends Biochem. Sci. 29 (2004) 95-102
6. Soos T.J., Meijer L., and Nelson P.J. Drug News Perspect. 19 6 (2006) 325-328
7. Testard A., Logé C., Léger B., Robert J.-M., Lozach O., Blairvacq M., Meijer L., Thiéry V., and Besson T. Bioorg. Med. Chem. Lett. 16 (2006) 3419-3423
8. Besson T., Thiéry V., and Dubac J. In: Loupy A. (Ed). Microwaves in Organic Synthesis (2006), Wiley-VCH Verlag Gmbh & Co. KGaA, Weinheim 416-455
9. Besson T., and Thiéry V. In: Van der Eycken E., Kappe O., and Gupta R.R. (Eds). Microwave-Assisted Synthesis of Heterocycles Series: Topics in Heterocyclic Chemistry Vol. 1 (2006), Springer 59-78
10. Testard A., Picot L., Fruitier-Arnaudin I., Piot J.M., Chabane H., Domon L., Thiéry V., and Besson T. J. Enzyme Inhib. Med. Chem. 19 (2004) 467-473
11. Alexandre F.R., Berecibar A., Wrigglesworth R., and Besson T. Tetrahedron Lett. 44 (2003) 4455-4458
12. Appel R., Janssen H., Siray M., and Knoch F. Chem. Ber. 118 (1985) 1632-1643
13. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., and Bourne P.E. Nucleic Acids Res. 28 (2000) 235-242. http://www.rcsb.org/pdb/
14. McInnes C., and Fischer P.M. Curr. Pharm. Des. 11 (2005) 1845-1863
15. Keri G., Orfi L., Eros D., Hegymegi-Barakonyi B., Szantai-Kis C., Horvath Z., Waczek F., Marosfalvi J., Szabadkai1 I., Pato J., Greff Z., Hafenbradl D., Daub H., Muller G., Klebl B., and Ullrich A. Curr. Signal Transduct Ther. 1 (2006) 67-95
16. Primot A., Baratte B., Gompel M., Borgne A., Liabeuf S., Romette J.L., Costantini F., and Meijer L. Protein Exp. Purif. 20 (2000) 394-404
17. Borgne A., and Meijer L. J. Biol. Chem. 271 (1996) 27847-27854
18. De Azevedo W.F., Leclerc S., Meijer L., Havlicek L., Strnad M., and Kim S.H. Eur. J. Biochem. 243 (1997) 518-526
19. Sybyl 7.2, Tripos Associates, Inc. 1699 South Hanley Road, St. Louis, MO 63144, USA.
20. Clarck M., Cramer III R.D., and Van Opdenbosch N. J. Comput. Chem. 10 (1989) 982-1012
21. Jones G., Willet P., and Glen R.C. J. Mol. Biol. 267 (1997) 727-748
22. Wang R., Lai L., and Wang S. J. Comput. Aided Mol. Des. 16 (2002) 11-26
23. Stewart J.J. J. Comput. Aided Mol. Des. 4 (1990) 1-45