Synthesis, biological evaluation, and molecular modeling of natural and unnatural flavonoidal alkaloids, inhibitors of kinases

Journal of Medicinal Chemistry

Volumn 55, Issue 6, 2012, Pages 2811-2819

  Nguyen, Thanh Binh ^a   Lozach, Olivier ^b   Surpateanu, Georgiana ^a   Wang, Qian ^c   Retailleau, Pascal ^a   Iorga, Bogdan I ^a   Meijer, Laurent ^b,d   Guéritte, Françoise ^a  

^a CNRS   (France)

^b STATION BIOLOGIQUE   (France)

^c EPFL   (Switzerland)

^d Centre de Perharidy   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; PROTEIN KINASE;

ARTICLE; HUMAN; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKALOIDS; ANIMALS; BIOLOGICAL AGENTS; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; DATABASES, FACTUAL; ENZYME ASSAYS; FLAVONOIDS; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863356201     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201727w     Document Type: Article

References (32)

1. Diaz-Padilla, I.; Siu, L. L.; Duran, I. Cyclin-dependent kinase inhibitors as potential targeted anticancer agents Invest. New Drugs 2009, 27, 586-594
2. Meijer, L.; Flajolet, M.; Greengard, P. Pharmacological inhibitors of glycogen synthase kinase 3 Trends Pharmacol. Sci. 2004, 25, 471-480 (Pubitemid 39149703)
3. Park, J.; Song, W.-J.; Chung, K. C. Function and regulation of Dyrk1A: towards understanding Down syndrome Cell. Mol. Life Sci. 2009, 66, 3235-3240
4. Moeslein, F. M.; Myers, M. P.; Landreth, G. E. The CLK family kinases, CLK1 and CLK2, phosphorylate and activate the tyrosine phosphatase, PTP-1B J. Biol. Chem. 1999, 274, 26697-26704
5. Ahond, A.; Fournet, A.; Moretti, C.; Philogene, E.; Poupat, C.; Thoison, O.; Potier, P. Premiers Alcaloides vrais isolés de Combré tacées, Buchenavia macrophylla Eichl. et Buchenavia capitata Eichl Bull. Soc. Chim. Fr. 1984, 1-2 (Pt 2) 41-45
6. Beutler, J. A.; Cardellina, J. H., II; McMahon, J. B.; Boyd, M. R. Anti-HIV and cytotoxic alkaloids from Buchenavia capitata J. Nat. Prod. 1992, 55, 207-213
7. Khoo, B. Y.; Chua, S. L.; Balaram, P. Apoptotic Effects of Chrysin in Human Cancer Cell Lines Int. J. Mol. Sci. 2010, 11, 2188-2199
8. Senderowicz, A. M. Flavopiridol: the first cyclin-dependent kinase inhibitor in human clinical trials Invest. New Drugs 1999, 17, 313-320 (Pubitemid 30037961)
9. Raje, N.; Hideshima, T.; Mukherjee, S.; Raab, M.; Vallet, S.; Chhetri, S.; Cirstea, D.; Pozzi, S.; Mitsiades, C.; Rooney, M.; Kiziltepe, T.; Podar, K.; Okawa, Y.; Ikeda, H.; Carrasco, R.; Richardson, P. G.; Chauhan, D.; Munshi, N. C.; Sharma, S.; Parikh, H.; Chabner, B.; Scadden, D.; Anderson, K. C. Preclinical activity of P276-00, a novel smallmolecule cyclin-dependent kinase inhibitor in the therapy of multiple myeloma Leukemia 2009, 23, 961-970
10. Liu, T.; Xu, Z.; He, Q.; Chen, Y.; Yang, B.; Hu, Y. Nitrogen-containing flavonoids as CDK1/cyclin B inhibitors: design, synthesis, and biological evaluation Bioorg. Med. Chem. Lett. 2007, 17, 278-281 (Pubitemid 44959950)
11. Zhang, S.; Ma, J.; Bao, Y.; Yang, P.; Zou, L.; Li, K.; Sun, X. Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: synthesis, SAR analysis, and biological activity Bioorg. Med. Chem. 2008, 16, 7127-7132
12. Johns, S. R.; Russel, J. H.; Hefferman, M. L. Ficine, A novel flavonoidal alkaloid from Ficus pantoniana Tetrahedron Lett. 1965, 24, 1987-1991
13. Leete, E. One-Step Synthesis of Ficine and Isoficine J. Nat. Prod. 1982, 45, 605-607
14. Nguyen, T.-B.; Wang, Q.; Guéritte, F. An efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoidal alkaloids through phenolic Mannich reaction of flavonoid and cyclic imines Eur. J. Org. Chem. 2011, 7076-7079
15. Wessely, F.; Moser, G. H. Synthese und Konstitution des Skutellareins Monatsh. Chem. 1930, 56, 97-105
16. Shinomiya, K.; Hano, Y.; Nomura, T. Mechanism on one-sided Wessely-Moser Rearrangement Reaction Heterocycles 2000, 53, 877-886
17. Berman, H. M.; Battistuz, T.; Bhat, T. N.; Bluhm, W. F.; Bourne, P. E.; Burkhardt, K.; Feng, Z.; Gilliland, G. L.; Iype, L.; Jain, S.; Fagan, P.; Marvin, J.; Padilla, D.; Ravichandran, V.; Schneider, B.; Thanki, N.; Weissig, H.; Westbrook, J. D.; Zardecki, C. The Protein Data Bank Acta Crystallogr., Sect. D: Biol. Crystallogr. 2002, 58, 899-907 (Pubitemid 34653017)
18. Mapelli, M.; Massimiliano, L.; Crovace, C.; Seeliger, M. A.; Tsai, L. H.; Meijer, L.; Musacchio, A. Mechanism of CDK5/p25 binding by CDK inhibitors J. Med. Chem. 2005, 48, 671-679 (Pubitemid 40209090)
19. Aoki, M.; Yokota, T.; Sugiura, I.; Sasaki, C.; Hasegawa, T.; Okumura, C.; Ishiguro, K.; Kohno, T.; Sugio, S.; Matsuzaki, T. Structural insight into nucleotide recognition in tau-protein kinase I/glycogen synthase kinase 3 beta Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 439-446 (Pubitemid 41087571)
20. Hamdouchi, C.; Zhong, B.; Mendoza, J.; Collins, E.; Jaramillo, C.; De Diego, J. E.; Robertson, D.; Spencer, C. D.; Anderson, B. D.; Watkins, S. A.; Zhang, F.; Brooks, H. B. Structure-based design of a new class of highly selective aminoimidazo[1,2- a ]pyridine-based inhibitors of cyclin dependent kinases Bioorg. Med. Chem. Lett. 2005, 15, 1943-1947 (Pubitemid 40385098)
21. Baumli, S.; Lolli, G.; Lowe, E. D.; Troiani, S.; Rusconi, L.; Bullock, A. N.; Debreczeni, J. E.; Knapp, S.; Johnson, L. N. The structure of P-TEFb (CDK9/cyclin T1), its complex with flavopiridol and regulation by phosphorylation EMBO J. 2008, 27, 1907-1918
22. Bettayeb, K.; Oumata, N.; Echalier, A.; Ferandin, Y.; Endicott, J. A.; Galons, H.; Meijer, L. CR8, a potent and selective, roscovitine-derived inhibitor of cyclin-dependent kinases Oncogene 2008, 27, 5797-5807
23. Primot, A.; Baratte, B.; Gompel, M.; Borgne, A.; Liabeuf, S.; Romette, J. L.; Costantini, F.; Meijer, L. Purification of GSK-3 by affinity chromatography on immobilised axin Protein Expression Purif. 2000, 20, 394-404
24. 5 units: one step synthesis of complex polycyclic alkaloids from the Nitraria genus Tetrahedron 2006, 62, 5248
25. Nomura, Y.; Ogawa, K.; Takeuchi, Y.; Tomoda, S. One-Step Synthesis and Structural Confirmation of 1-Pyrroline Trimer Chem. Lett. 1977, 6, 693
26. Šali, A.; Potterton, L.; Yuan, F.; van Vlijmen, H.; Karplus, M. Evaluation of comparative protein modeling by MODELLER Proteins: Struct., Funct., Bioinf. 1995, 23, 318-326
27. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice Nucleic Acids Res. 1994, 22, 4673-4680 (Pubitemid 24354800)
28. CORINA, version 3.44; Molecular Networks GmbH: Erlangen, Germany, 2008; http://www.molecular-networks.com (Accessed December 15, 2011).
29. LigPrep, version 2.5; Schrödinger, LLC: New York, 2011; http://www.schrodinger.com (Accessed December 15, 2011).
30. Verdonk, M. L.; Cole, J. C.; Hartshorn, M. J.; Murray, C. W.; Taylor, R. D. Improved protein-ligand docking using GOLD Proteins: Struct., Funct., Bioinf. 2003, 52, 609-623 (Pubitemid 37034158)
31. Maestro, version 9.2; Schrödinger, LLC: New York, 2011; http://www.schrodinger.com (Accessed December 15, 2011).
32. The PyMOL Molecular Graphics System, version 0.99; DeLano Scientific: Palo Alto, CA, 2006; http://www.pymol.org (Accessed December 15, 2011).