Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: Synthesis, biological evaluation and structure-activity relationships. Part 2

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 23, 2009, Pages 7850-7860

  Horiuchi, Takao ^a   Nagata, Motoko ^a   Kitagawa, Mayumi ^a   Akahane, Kouichi ^a   Uoto, Kouichi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

Cyclin D1 CDK4 inhibitor; Thieno 2,3 d pyrimidin 4 yl hydrazone

Indexed keywords

4 [(METHYLAMINO)METHYL]BENZALDEHYDE (6 TERT BUTYLTHIENO[2,3 D]PYRIMIDIN 4 YL)HYDRAZONE; 5 ISOINDOLINECARBALDEHYDE (6 TERT BUTYLTHIENO[2,3 D]PYRIMIDIN 4 YL)HYDRAZONE; CYCLIN D1; CYCLIN DEPENDENT KINASE 4; THIENO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CYCLIN-DEPENDENT KINASES; HUMANS; HYDRAZONES; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, NUDE; MODELS, MOLECULAR; NEOPLASMS, EXPERIMENTAL; PROTEIN KINASE INHIBITORS; PYRIMIDINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 71849115791     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.039     Document Type: Article

References (39)

1. Hunter T., and Pines J. Cell 79 (1994) 573
2. Sherr C. Science 274 (1996) 1672
3. Morgan D.O. Annu. Rev. Cell Dev. Biol. 13 (1997) 261
4. Pines J. Trends Biochem. Sci. 18 (1993) 195
5. Pines J. Nat. Cell Biol. 1 (1999) E73
6. Shapiro G.I. J. Clin. Oncol. 24 (2006) 1770
7. Khleif S.N., DeGregori J., Yee C.L., Otterson G.A., Kaye F.J., Nevins J.R., and Howley P.M. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 4350
8. Dyson N. Gene Dev. 12 (1998) 2245
9. Sandhu C., and Slingerland J. Cancer Detect. Prev. 24 (2000) 107
10. Bringold F., and Serrano M. Exp. Gerontol. 35 (2000) 317
11. Roussel M.F. Oncogene 18 (1999) 5311
12. Nevins J.R. Hum. Mol. Gen. 10 (2001) 699
13. Barnes D.M., and Gillett C.E. Breast Cancer Res. Treat. 52 (1998) 1
14. Malumbres M., and Barbacid M. Cancer Cell 9 (2006) 2
15. Tetsu O., and McCormick F. Cancer Cell 3 (2003) 233
16. Buolamwini J.K. Curr. Pharm. Des. 6 (2000) 379
17. Sanderowicz A.M. Cancer Biol. Ther. 2 (2003) S84
18. Hirai H., Kawanishi N., and Iwasawa Y. Curr. Top. Med. Chem. 5 (2005) 167
19. Naik R.G., Kattige S.L., Bhat S.V., and Alreja B. Tetrahedron 44 (1988) 2081
20. Worland P.J., Kaur G., Stetler-Stevenson M., Sehers S., Sartor O., and Sausville E.A. Biochem. Pharmacol. 46 (1993) 1831
21. Carlson B.A., Dubay M.M., Sausville E.A., Brizuela L., and Worland P.J. Cancer Res. 56 (1996) 2973
22. Takahashi I., Saitoh Y., Yoshida M., Sano H., Nakano H., Morimoto M., and Tamaoki T. J. Antibiot. 42 (1989) 571
23. Akinaga S., Gomi K., Morimoto M., Tamaoki T., and Okabe M. Cancer Res. 51 (1991) 4888
24. Seynaeve C.M., Stetler-Stevenson M., Sebers S., Kaur G., Sausville E.A., and Worland P.J. Cancer Res. 53 (1993) 2081
25. Vesely J., Havlicek L., Strnad M., Blow J.J., Donella-Deana A., Pinna L., Letham D.S., Kato J., Detivaud L., Leclerc S., and Meijer L. Eur. J. Biochem. 224 (1994) 771
26. Havlicek L., Hanus J., Vesely J., Leclerc S., Meijer L., Shaw G., and Strnad M. J. Med. Chem. 40 (1997) 408
27. Wang S., McClue S.J., Ferguson J.R., Hull J.D., Stokes S., Parson S., Westwood R., and Fischer P.M. Tetrahedron: Asymmetry 12 (2001) 2891
28. Fry D.W., Harvey P.J., Keller P.R., Elliott W.L., Meade M., Trachet E., Albassam M., Zheng X., Leopold W.R., Pryer N.K., and Toogood P.L. Mol. Cancer Ther. 3 (2004) 1427
29. VanderWel S.N., Harvey P.J., McNamara D.J., Repine J.T., Keller P.R., Quin III J., Booth R.J., Elliott W.L., Dobrusin E.M., Fry D.W., and Toogood P.L. J. Med. Chem. 48 (2005) 2371
30. Toogood P.L., Harvey P.J., Repine J.T., Sheehan D.J., VanderWel S.N., Zhou H., Keller P.P., McNamara D.J., Sherry D., Zhu T., Brodfuehrer J., Choi C., Barvian M.R., and Fry D.W. J. Med. Chem. 48 (2005) 2388
31. Horiuchi T., Chiba J., Uoto K., and Soga T. Bioorg. Med. Chem. Lett. 19 (2009) 305
32. Russo A.A., Jeffrey P.D., and Pavletich N.P. Nat. Struct. Biol. 3 (1996) 696
33. Brotherton D.H., Dhanaraj V., Wick S., Brizuela L., Domaille P.J., Volyanik E., Xu X., Parisini E., Smith B.O., Archer S.J., Serrano M., Brenner S.L., Blundell T.L., and Laue E.D. Nature 395 (1998) 244
34. Day P.J., Cleasby A., Tickle I.J., O'Reilly M., Coyle J.E., Holding F.P., McMenamin R.L., Yon J., Chopra R., Lengauer C., and Jhoti H. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 4166
35. Takaki T., Echalier A., Brown N.R., Hunt T., Endicott J.A., and Noble M.E. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 4171
36. Tinney F.J., Cetenko W.A., Kerbleski J.J., Connor D.T., Sorenson R.J., and Herzig D.J. J. Med. Chem. 24 (1981) 878
37. Hozien Z.A., Atta F.M., Hassan Kh.M., Abdel-Wahab A.A., and Ahmed S.A. Synth. Commun. 26 (1996) 3733
38. Middleton D.S., Maw G.N., Challenger C., Jessiman A., Johnson P.S., Million W.A., Nichols C.L., Price J.A., and Trevethick M. Bioorg. Med. Chem. Lett. 16 (2006) 905
39. Haginoya N., Kobayashi S., Komoriya S., Yoshino T., Suzuki M., Shimada T., Watanabe K., Hirokawa Y., Furugori T., and Nagahara T. J. Med. Chem. 47 (2004) 5167