Synthesis and antiproliferative activity of 7-azaindirubin-3′-oxime, a 7-aza isostere of the natural indirubin pharmacophore

Journal of Natural Products

Volumn 72, Issue 12, 2009, Pages 2199-2202

  Kritsanida, Marina ^a   Magiatis, Prokopios ^a   Skaltsounis, Alexios Leandros ^a   Peng, Youyi ^b   Li, Peng ^b   Wennogle, Lawrence P ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b Intra Cellular Therapies Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIBROMO 3H PYRROLE [2,3 B]PYRIDINE; 3' OXIME DERIVATIVE; 5 BROMO 7,7' DIAZA 1,1' DIMETHYLISOINDIGO; 7 AZA 1 METHYLINDIRUBIN; 7 AZA 1 METHYLINDIRUBIN 3' OXIME; 7 AZAINDIRUBIN; 7 AZAINDIRUBIN 3' OXIME; 7 AZAISATIN; 7,7' DIAZA 1,1' DIMETHYLISOINDIGO; INDIRUBIN; INDOLE DERIVATIVE; OXIME DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; DRUG ACTIVITY; INHIBITION KINETICS; PHARMACOPHORE; SYNTHESIS;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; CYCLIN-DEPENDENT KINASE INHIBITOR PROTEINS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; INDOLE ALKALOIDS; INDOLES; MOLECULAR STRUCTURE;

EID: 74049099787     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np9003905     Document Type: Article

References (25)

1. Hoessel, R.; Leclerc, S.; Endicott, J.; Noble, M.; Lawrie, A.; Tunnah, P.; Leost, M.; Damiens, E.; Marie, D.; Marko, D.; Niederberger, E.; Tang, W.; Eisenbrand, G.; Meijer, L. Nat. Cell Biol. 1999, 1, 60-67.
2. Balfour-Paul, J. Indigo; British Museum Press: London, 1998.
3. Meijer, L.; Skaltsounis, A. L.; Magiatis, P.; Polychronopoulos, P.; Knockaert, M.; Leost, M.; Ryan, X. P.; Vonica, C. D.; Brivanlou, A.; Dajani, R.; Tarricone, A.; Musacchio, A.; Roe, S. M.; Pearl, L.; Greengard, P. Chem. Biol. 2003, 10, 1255-1266.
4. Cooksey, C. J. Molecules 2001, 6, 736-769.
5. Guengerich, F. P.; Sorrells, J. L.; Schmitt, S.; Krauser, J. A.; Aryal, P.; Meijer, L. J. Med. Chem. 2004, 47, 3236-3241.
6. Wu, Z. L.; Aryal, P.; Lozach, O.; Meijer, L.; Guengerich, F. P. Chem. Biodiversity 2005, 2, 51-65.
7. Adachi, J.; Mori, Y.; Matsui, S.; Takigami, H.; Fujino, J.; Kitagawa, H.; Miller, C. A., 3rd; Kato, T.; Saeki, K.; Matsuda, T. J. Biol. Chem. 2001, 276, 31475-31478.
8. Xiao, Z.; Hao, Y.; Liu, B.; Qian, L. Leuk. Lymphoma 2002, 43, 1763-1768.
9. Leclerc, S.; Garnier, M.; Hoessel, R.; Marko, D.; Bibb, J. A.; Snyder, G. L.; Greengard, P.; Biernat, J.; Mandelkow, E. M.; Eisenbrand, G.; Meijer, L. J. Biol. Chem. 2001, 276, 251-260.
10. Myrianthopoulos, V.; Magiatis, P.; Ferandin, Y.; Skaltsounis, A. L.; Meijer, L.; Mikros, E. J. Med. Chem. 2007, 50, 4027-4037.
11. Kawanishi, M.; Sakamoto, M.; Ito, A.; Kishi, K.; Yagi, T. Mutat. Res. 2003, 540, 99-105.
12. Marko, D.; Schätzle, S.; Friedel, A.; Genzlinger, A.; Zankl, H.; Meijer, L.; Eisenbrand, G. Br. J. Cancer 2001, 84, 283-289.
13. Damiens, E.; Baratte, B.; Marie, D.; Eisenbrand, G.; Meijer, L. Oncogene 2001, 20, 3786-3797.
14. Knockaert, M.; Blondel, M.; Bach, S.; Leost, M.; Elbi, C.; Hager, G.; Naggy, S. R.; Han, D.; Denison, M.; Ffrench, M.; Ryan, X. P.; Magiatis, P.; Polychronopoulos, P.; Greengard, P.; Skaltsounis, L.; Meijer, L. Oncogene 2004, 23, 4400-4412.
15. Nam, S.; Buettner, R.; Turkson, J.; Kim, D.; Cheng, J. Q.; Muehlbeyer, S.; Hippe, F.; Vatter, S.; Merz, K. H.; Eisenbrand, G.; Jove, R. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 5998-6003.
16. Polychronopoulos, P.; Magiatis, P.; Skaltsounis, A. L.; Myrianthopoulos, V.; Mikros, E.; Tarricone, A.; Musacchio, A.; Roe, S. M.; Pearl, L.; Leost, M.; Greengard, P.; Meijer, L. J. Med. Chem. 2004, 47, 935-946.
17. Ferandin, Y.; Bettayeb, K.; Kritsanida, M.; Lozach, O.; Polychronopoulos, P.; Magiatis, P.; Skaltsounis, A. L.; Meijer, L. J. Med. Chem. 2006, 49, 4638-4649.
18. Ribas, J.; Bettayeb, K.; Ferandin, Y.; Garrofé-Ochoa, X.; Knockaert, M.; Totzke, F.; Schächtele, C.; Mester, J.; Polychronopoulos, P.; Magiatis, P.; Skaltsounis, A. L.; Boix, J.; Meijer, L. Oncogene 2006, 25, 6304-6318.
19. Vougogiannopoulou, K.; Ferandin, Y.; Bettayeb, K.; Myrianthopoulos, V.; Lozach, O.; Fan, Y.; Johnson, C. H.; Magiatis, P.; Skaltsounis, A.-L.; Mikros, E.; Meijer, L. J. Med. Chem. 2008, 51, 6421-6431.
20. Sato, N.; Meijer, L.; Skaltsounis, A. L.; Greengard, P.; Brivanlou, A. Nat. Med. 2004, 10, 55-63.
21. Wang, Z. H.; Li, W. Y.; Li, F. L.; Zhang, L.; Hua, W. Y.; Cheng, J. C.; Yao, Q. Z. Chin. Chem. Lett. 2009, 20, 542-544.
22. Kim, S.-H.; Choi, S. J.; Kim, Y.-C.; Kuh, H.-J. Arch. Pharm. Res. 2009, 32, 915-922.
23. Tatsugi, J.; Zwiwei, T.; Izawa, Y. Arkivok 2001, 67-73.
24. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589-601.
25. Boyd, M. R.; Paull, K. D. Drug Dev. Res. 1995, 34, 91-109.