Synthesis and evaluation of novel 7-azaindazolyl-indolyl-maleimide derivatives as antitumor agents and protein kinase C inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 13, 2009, Pages 4763-4772

  Ye, Qing ^a   Cao, Ji ^a   Zhou, Xinglu ^a   Lv, Dan ^a   He, Qiaojun ^a   Yang, Bo ^a   Hu, Yongzhou ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

7 Azaindazolyl indolyl maleimides; Antiproliferative activity; PKC inhibition

Indexed keywords

3 (1 METHYL 1H INDOL 3 YL) 1 PHENYL 4 [1 [3 (PIPERIDIN 1 YL)PROPYL] 1H PYRAZOLO[3,4 B]PYRIDINE 3 YL] 1H PYRROLE 2,5 DIONE; 7 AZAINDAZOLYLINDOLYLMALEIMIDE DERIVATIVE; 7 HYDROXYSTAUROSPORINE; ANTINEOPLASTIC AGENT; ENZASTAURIN; MALEIMIDE DERIVATIVE; MIDOSTAURIN; PROTEIN KINASE C INHIBITOR; RO 31 6233; RO 316233; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; MITOCHONDRIAL MEMBRANE; NONHUMAN;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; MALEIMIDES; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 66449116904     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.043     Document Type: Article

References (26)

1. Ohkubo M., Kawamoto H., Ohno T., Nakano M., and Morishima H. Tetrahedron 53 (1997) 585
2. Kanzawa F., Nishio K., Kubota N., and Saijo N. Cancer Res. 55 (1995) 2806
3. Komatani H., Kotani H., Hara Y., Nakagawa R., Matsumoto M., Arakawa H., and Nishimura S. Cancer Res. 61 (2001) 2827
4. Akinaga S., Sugiyama K., and Akiyama T. Anti-Cancer Drug Des. 15 (2000) 43
5. Meyer T., Regenass U., Fabbro D., Alteri E., Rösel J., Müller M., Caravatti G., and Matter A. Int. J. Cancer 43 (1989) 851
6. Faul M.M., Gillig J.R., Jirousek M.R., Ballas L.M., Schotten T., Kahl A., and Mohr M. Bioorg. Med. Chem. Lett. 13 (2003) 1857
7. Pereira E.R., Fabre S., Sancelme M., Prudhomme M., and Rapp M. J. Antibiot. 48 (1995) 863
8. Jirousek M.R., Gillig J.R., Heath W.F., McDonald J.H., Neel D.A., Rito C.J., Singh U., Stramm L.E., Melikian-Badnlian A., Baevsky M., Ballas L.M., Hall S.E., Winneroski L.L., and Faul M.M. J. Med. Chem. 39 (1996) 2664
9. Kleinschrroth J., Harteinstein J., Rudolph C., and Schächtele C.J. Bioorg. Med. Chem. Lett. 3 (1993) 1959
10. Davis P.D., Hill C.H., Lawton G., Nixon J.S., Wilkinson S.E., Hurst S.A., Keech E., and Turner S.E. J. Med. Chem. 35 (1992) 177
11. Davis P.D., Elliott L.H., Harris W., Hill C.H., Hurst S.A., Keech E., Kumar M.K.H., Lawton G., Nixon J.S., and Wilkinson S.E. J. Med. Chem. 35 (1992) 994
12. Tanaka M., Sagawa S., Hoshi J., Shimoma F., Matsuda I., Sakoda K., Sasase T., Shindo M., and Inaba T. Bioorg. Med. Chem. Lett. 14 (2004) 5171
13. Lynch B.M., Khan M.A., and Teo H.C. Can. J. Chem. 66 (1988) 420
14. Kocevar M., Stanovnik B., and Tisler M. J. Heterocycl. Chem. 15 (1978) 1175
15. Zhang, H.-C.; Maryanoff, B.; Conway, B.; White, K.; Ye, H.; Hecker, L. R.; McComsey, D. F.; WO 2002046183, 2003.
16. Howard M.R. J. Org. Chem. 23 (1972) 3630
17. Michel G., James T.L., and Samuel J.D. J. Org. Chem. 58 (1993) 343
18. Zhang, H.-C.; Kho, G. H.; Maryanoff, B. E.; Ye, H.; Shen, L. WO 2003095452, 2003.
19. Mitsuru O., Teruyuki N., Hideki J., Teruki H., and Hajime M. Tetrahedron 24 (1996) 8099
20. Michael B., Hans R., Bert S., and Wolfgang S. Tetrahedron 10 (1988) 2887
21. Akao A., Hiraga S., and Iida T. Tetrahedron 57 (2001) 8917
22. Krayushkin M.M., Shirinyan V.Z., Belenkii L.I., Shimlin A.A., Martyn-kin A.Y., and Uzhinov B.M. Russ. J. Org. Chem. 38 (2002) 1335
23. Luo P.H., He Q.J., and Yang B. Mol. Cancer Ther. 5 (2006) 962
24. Fang L., He Q.J., Hu Y.Z., and Yang B. Cancer Chem. Pharm. 59 (2007) 397
25. Katiyar S.K., Roy A.M., and Baliga M.S. Mol. Cancer Ther. 4 (2005) 207
26. Marijan K., Branko S., and Miha T. Monatsh. Chem. 119 (1988) 597