Synthesis and biological evaluations of pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 inhibitors

European Journal of Medicinal Chemistry

Volumn 38, Issue 5, 2003, Pages 525-532

  Kim, Dong Chan ^a   Lee, Yeo Ran ^a   Yang, Beom Seok ^a   Shin, Kye Jung ^a   Kim, Dong Jin ^a   Chung, Bong Young ^b   Yoo, Kyung Ho ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Korea University   (South Korea)

Author keywords

CDK; CDK2 inhibitory activity; Cell growth inhibitory activity; Kinase inhibitors; Pyrazolo 3,4 d pyrimidines

Indexed keywords

1 ALKYL 4 AMINO 6 HYDROXYLAMINOPYRAZOLO[3,4 D]PYRIMIDINE; 1 ALKYL 4 AMINO 6 METHYLMERCAPTOPYRAZOLO[3,4 D]PYRIMIDINE; 1 ALKYL 4 AMINO 6 METHYLSULFONYLPYRAZOLO[3,4 D]PYRIMIDINE; 1,4,6 PYRAZOLO[3,4 D]PYRIMIDINE; 4 AMINO 6 METHYLMERCAPTOPYRAZOLO[3,4 D]PYRIMIDINE; CYCLIN DEPENDENT KINASE INHIBITOR; OLOMOUCINE; PYRAZOLO[3,4 D]PYRIMIDINE; PYRIMIDINE DERIVATIVE; ROSCOVITINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DERIVATIZATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL;

EID: 0038060520     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(03)00065-5     Document Type: Article

References (35)

1. Aaronson S.A. Science. 254:1991;1146.
2. Meijer L. Trends Cell Biol. 6:1996;393-397.
3. Meijer L., Kim S.-H. Methods Enzymol. 283:1997;113-128.
4. Coleman K.G., Lyssikatos J.P., Ynag B.V. Annu. Rep. Med. Chem. 32:1997;171-179.
5. Gray N.S., Wodicka L., Thunnissen A.-M.W.H., Norman T.C., Kwon S., Espinoza F.H., Morgan D.O., Barnes G., Leclerc S., Meijer L., Kim S.-H., Lockhart D.J., Schultz P.G. Science. 281:1998;533-538.
6. Legraverend M., Tunnah P., Noble M., Ducrot P., Ludwig O., Grierson D.S., Leost M., Meijer L., Endicott J. J. Med. Chem. 43:2000;1282-1292.
7. Oh C.H., Kim H.K., Lee S.C., Oh C., Yang B.S., Rhee H.J., Cho J.H. Arch. Pharm. Pharm. Med. Chem. 334:2001;345-350.
8. Legraverend M., Ludwig O., Leclerc S., Meijer L. J. Heterocycl. Chem. 38:2001;299-303.
9. Chang Y.T., Gray N.S., Rosania G.R., Sutherlin D.P., Kwon S., Norman T.C., Sarohia R., Leost M., Meijer L., Schultz P.G. Chem. Biol. 6:1999;361-375.
10. Schow S.R., Mackman R.L., Blum C.L., Brooks E., Horsma A.G., Joly A., Kerwar S.S., Lee G., Shiffman D., Nelson M.G., Wang X., Wick M.M., Zhang X., Lum R.T. Bioorg. Med. Chem. Lett. 7:1997;2697-2702.
11. Imbach P., Capraro H.G., Furet P., Mett H., Meyer T., Zimmermann J. Bioorg. Med. Chem. Lett. 9:1999;91-96.
12. Rewcastle G.W., Denny W.A., Bridges A.J., Zhou H., Cody D.R., McMichael A., Fry D.W. J. Med. Chem. 38:1995;3482-3487.
13. A.J. Barker, Eur. Pat. Appl. 566 226 A1, 1993.
14. Smail J.B., Palmer B.D., Rewcastle G.W., Denny W.A., McNamara D.J., Dobrusin E.M., Bridges A.J., Zhou H., Showalter H.D.H., Winters R.T., Leopold W.R., Fry D.W., Nelson J.M., Slintak V., Elliot W.L., Roberts B.J., Vincent P.W., Patmore S.J. J. Med. Chem. 42:1999;1803-1815.
15. Bridges A.J., Zhou H., Cody D.R., Rewcastle G.W., McMichael A., Showalter H.D.H., Fry D.W., Kraker A.J., Denny W.A. J. Med. Chem. 39:1996;267-276.
16. Nigg E.A. Trends Cell Biol. 3:1993;296-301.
17. Sherr C.S. Cell. 73:1993;1059-1065.
18. Hartwell L.H., Kastan M.B. Science. 266:1994;1821-1828.
19. Morgan D.O. Annu. Rev. Cell Dev. Biol. 13:1997;261-291.
20. Grana X., Reddy E.P. Oncogene. 11:1995;211-219.
21. Morgan D.O. Nature. 374:1995;131-134.
22. Pines J. Biochem. J. 308:1995;697-711.
23. Vesely J., Havlicek L., Strnad M., Blow J.J., Donella-Deana A., Pinna L., Letham D.S., Kato J., Detivaud L., Leclerc S., Meijer L. Eur. J. Biochem. 224:1994;771-786.
24. Meijer L., Borgne A., Mulner O., Chong J.P.J., Blow J.J., Inagaki N., Inagaki M., Delcros J.-G., Moulinoux J.-P. Eur. J. Biochem. 224:1994;771-786.
25. Parker C.W., Entsch B., Letham D.S. Phytochemistry. 25:1986;303-310.
26. Abraham R.T., Axquarone M., Andersen A., Asensi A., Bellé R., Berger F., Bergounioux C., Brunn G., Buquet-Fargot C., Fagot D., Glab N., Goudeau H., Goudeau M., Guettier P., Houghton P.J., Hendriks H., Kloareg B., Lippai M., Marie D., Maro B., Meijer L., Mester J., Mulner-Lorillon O., Poulet S.A., Schierenberg E., Schutte B., Vaulot D., Verlhac M.H. Biol. Cell. 83:1995;105-120.
27. Meijer L., Borgne A., Mulner O., Chong J.P.J., Blow J.J., Inagaki N., Inagaki M., Delcros J.-G., Moulinoux J.-P. Eur. J. Biochem. 243:1997;527-536.
28. Hevlicek L., Hanus J., Vesely J., Leclerc S., Meijer L., Shaw G., Strnad M. J. Med. Chem. 40:1997;408-412.
29. De Azevedo W.F., Leclerc S., Meijer L., Havlicek L., Strnad M., Kim S.H. Eur. J. Biochem. 243:1997;518-526.
30. Schulze-Gahmen U., Brandsen J., Jones H.D., Morgan D.O., Meijer L., Vesely J., Kim S.H. Proteins. 22:1995;378-391.
31. Furet P., Zimmermann J., Capraro H.G., Meyer T., Imbach P. J. Comput. Aid Mol. Des. 14:2000;403-409.
32. Robins R.K. J. Am. Chem. Soc. 79:1957;6407-6415.
33. Brown D.J., Ford P.W. J. Chem. Soc. Sect. C. 1967;568-572.
34. Toyota A., Katagiri N., Kaneko C. Heterocycles. 36:1993;1625-1630.
35. Lee J.Y., Park Y.K., So I.-S., Chung H.-K., Yang B.-S., Lee S.J., Park H., Lee Y.S. Arch. Pharm. Pharm. Med. Chem. 334:2001;357-360.