Novel purine-based fluoroaryl-1,2,3-triazoles as neuroprotecting agents: Synthesis, neuronal cell culture investigations, and CDK5 docking studies

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 13, 2011, Pages 3957-3961

  Nair, Nanditha ^a   Kudo, Wataru ^b   Smith, Mark A ^b   Abrol, Ravinder ^c   Goddard III, William A ^c   Reddy, V Prakash ^a  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

^b CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

ATP; CDK5; Cell cycle inhibitors; Docking methods; Flavopiridol; Neuroprotectors; Purine triazoles; Roscovitine

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 2 FLUOROPHENYLMETHYLTRIAZOLE; ADENOSINE TRIPHOSPHATE; AMYLOID BETA PROTEIN; COPPER; CYCLIN DEPENDENT KINASE 5; CYCLIN DEPENDENT KINASE INHIBITOR; FLAVOPIRIDOL; PENTAFLUOROPHENYLMETHYLTRIAZOLE; PROTEIN P25; PURINE DERIVATIVE; ROSCOVITINE; UNCLASSIFIED DRUG;

1,3 DIPOLAR CYCLOADDITION; ANIMAL CELL; APOPTOSIS; ARTICLE; BINDING SITE; CATALYST; CELL CYCLE REGULATION; CELL SURVIVAL; CONTROLLED STUDY; CYCLOADDITION; DRUG BINDING; DRUG SYNTHESIS; FLUORESCENCE ELECTRON MICROSCOPY; FLUORESCENCE MICROSCOPY; IN VITRO STUDY; MOLECULAR DOCKING; NERVE CELL; NERVE CELL CULTURE; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN;

ANIMALS; CELL CYCLE; CELLS, CULTURED; CYCLIN-DEPENDENT KINASE 5; FLAVONOIDS; FLUORINE; HIPPOCAMPUS; HUMANS; HYDROGEN BONDING; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEUROPROTECTIVE AGENTS; PIPERIDINES; PROTEIN KINASE INHIBITORS; PURINES; TRIAZOLES;

EID: 79958753408     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.05.019     Document Type: Article

References (46)

1. Lopes, J. P.; Oliveira, C. R.; Agostinho, P. Cell Cycle 2009, 8, 97.
2. Raina, A. K.; Monteiro, M. J.; McShea, A.; Smith, M. A. Int. J. Exp. Pathol. 1999, 80, 71.
3. Endo, R.; Saito, T.; Asada, A.; Kawahara, H.; Ohshima, T.; Hisanaga, S.-I. J. Biol Chem 2009, 284, 26029.
4. Hisanaga, S.-I.; Endo, R. J. Neurochem. 2010, 115, 1309.
5. Kamei, H.; Saito, T.; Ozawa, M.; Fujita, Y.; Asada, A.; Bibb, J. A.; Saido, T. C.; Sorimachi, H.; Hisanaga, S.-I. J. Biol. Chem. 2007, 282, 1687.
6. Lopes, J. P.; Oliveira, C. R.; Agostinho, P. Aging Cell 2010, 9, 64.
7. Tian, B.; Yang, Q.; Mao, Z. Nat. Cell Biol. 2009, 11, 211.
8. Patrick, G. N.; Zukerberg, L.; Nikolic, M.; de la Monte, S.; Dikkes, P.; Tsai, L. H. Nature 1999, 402, 615.
9. Piedrahita, D.; Hernandez, I.; Lopez-Tobon, A.; Fedorov, D.; Obara, B.; Manjunath, B. S.; Boudreau, R. L.; Davidson, B.; LaFerla, F.; Gallego-Gomez, J. C.; Kosik, K. S.; Cardona-Gomez, G. P. J. Neurosci. 2010, 30, 13966.
10. Laha, J. K.; Zhang, X.; Qiao, L.; Liu, M.; Chatterjee, S.; Robinson, S.; Kosik, K. S.; Cuny, G. D. Bioorg. Med. Chem. Lett. 2011, 21, 2098.
11. Glicksman, M. A.; Cuny, G. D.; Liu, M.; Dobson, B.; Auerbach, K.; Stein, R. L.; Kosik, K. S. Curr. Alzheimer Res. 2007, 4, 547.
12. Ahn, J. S.; Radhakrishnan, M. L.; Mapelli, M.; Choi, S.; Tidor, B.; Cuny, G. D.; Musacchio, A.; Yeh, L.-A.; Kosik, K. S. Chem. Biol. 2005, 12, 811.
13. Kanungo, J.; Zheng, Y.-I.; Amin, N. D.; Pant, H. C. Cell. Mol. Neurobiol. 2009, 29, 1073.
14. Hamdane, M.; Bretteville, A.; Sambo, A.-V.; Schindowski, K.; Begard, S.; Delacourte, A.; Bertrand, P.; Buee, L. J. Cell Sci. 2005, 118, 1291.
15. Sausville, E. A. Trends Mol. Med. 2002, 8, S32.
16. Helal, C. J.; Kang, Z.; Lucas, J. C.; Gant, T.; Ahlijanian, M. K.; Schachter, J. B.; Richter, K. E. G.; Cook, J. M.; Menniti, F. S.; Kelly, K.; Mente, S.; Pandit, J.; Hosea, N. Bioorg. Med. Chem. Lett. 2009, 19, 5703.
17. Jain, P.; Flaherty, P. T.; Yi, S.; Chopra, I.; Bleasdell, G.; Lipay, J.; Ferandin, Y.; Meijer, L.; Madura, J. D. Bioorg. Med. Chem. 2011, 19, 359.
18. Zheng, Y.-L.; Amin, N. D.; Hu, Y.-F.; Rudrabhatla, P.; Shukla, V.; Kanungo, J.; Kesavapany, S.; Grant, P.; Albers, W.; Pant, H. C. J. Biol. Chem. 2010, 285, 34202.
19. Akue-Gedu, R.; Debiton, E.; Ferandin, Y.; Meijer, L.; Prudhomme, M.; Anizon, F.; Moreau, P. Bioorg. Med. Chem. 2009, 17, 4420.
20. Beauchard, A.; Ferandin, Y.; Frere, S.; Lozach, O.; Blairvacq, M.; Meijer, L.; Thiery, V.; Besson, T. Bioorg. Med. Chem. 2006, 14, 6434.
21. Beauchard, A.; Laborie, H.; Rouillard, H.; Lozach, O.; Ferandin, Y.; Le Guevel, R.; Guguen-Guillouzo, C.; Meijer, L.; Besson, T.; Thiery, V. Bioorg. Med. Chem. 2009, 17, 6257.
22. Helal, C. J.; Sanner, M. A.; Cooper, C. B.; Gant, T.; Adam, M.; Lucas, J. C.; Kang, Z.; Kupchinsky, S.; Ahlijanian, M. K.; Tate, B.; Menniti, F. S.; Kelly, K.; Peterson, M. Bioorg. Med. Chem. Lett. 2004, 14, 5521.
23. Bettayeb, K.; Sallam, H.; Ferandin, Y.; Popowycz, F.; Fournet, G.; Hassan, M.; Echalier, A.; Bernard, P.; Endicott, J.; Joseph, B.; Meijer, L. Mol. Cancer Ther. 2008, 7, 2713.
24. Otyepka, M.; Bartova, I.; Kriz, Z.; Koca, J. J. Biol. Chem. 2006, 281, 7271.
25. Oumata, N.; Bettayeb, K.; Ferandin, Y.; Demange, L.; Lopez-Giral, A.; Goddard, M.-L.; Myrianthopoulos, V.; Mikros, E.; Flajolet, M.; Greengard, P.; Meijer, L.; Galons, H. J. Med. Chem. 2008, 51, 5229.
26. Basso, A. D.; Doll, R. J. Recent Pat. Anti-Cancer Drug Discovery 2006, 1, 357.
27. Krystof, V.; Uldrijan, S. Curr. Drug Targets 2010, 11, 291.
28. Malumbres, M.; Pevarello, P.; Barbacid, M.; Bischoff, J. R. Trends Pharmacol. Sci. 2008, 29, 16.
29. Wang, L. M.; Ren, D. M. Mini-Rev. Med. Chem. 2010, 10, 1058.
30. Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2003, 18, 303.
31. Anzahaee, M. Y.; Watts, J. K.; Alla, N. R.; Nicholson, A. W.; Damha, M. J. J. Am. Chem. Soc. 2011, 133, 728.
32. Dubowchik, G. M.; Vrudhula, V. M.; Dasgupta, B.; Ditta, J.; Chen, T.; Sheriff, S.; Sipman, K.; Witmer, M.; Tredup, J.; Vyas, D. M.; Verdoorn, T. A.; Bollini, S.; Vinitsky, A. Org. Lett. 2001, 3, 3987.
33. Di Magno, S. G.; Sun, H. Curr. Top. Med. Chem. 2006, 6, 1473.
34. Boehm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Mueller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637.
35. Shah, P.; Westwell, A. D. J. Enzyme Inhib. Med. Chem. 2007, 22, 527.
36. Pallas, M.; Canudas, A. M.; Verdaguer, E.; Allgaier, C.; Garcia de Arriba, S.; Alvira, D.; Sureda, F. X.; Camins, A. Curr. Med. Chem. Cent. Nerv. Syst. Agents 2005, 5, 101.
37. Rizzolio, F.; Tuccinardi, T.; Caligiuri, I.; Lucchetti, C.; Giordano, A. Curr. Drug Targets 2010, 11, 279.
38. Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev. 2009, 109, 4207.
39. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302.
40. Holub, J. M.; Kirshenbaum, K. Chem. Soc. Rev. 2010, 39, 1325.
41. Camins, A.; Verdaguer, E.; Folch, J.; Canudas, A. M.; Pallas, M. Drug News Perspect. 2006, 19, 453.
42. DerHovanessian, A.; Rablen, P. R.; Jain, A. J. Phys. Chem. A 2000, 104, 6056.
43. Alvira, D.; Ferrer, I.; Gutierrez-Cuesta, J.; Garcia-Castro, B.; Pallas, M.; Camins, A. Parkinsonism Relat. Disord. 2008, 14, 309.
44. Floriano, W. B.; Vaidehi, N.; Zamanakos, G.; Goddard, W. A., III J. Med. Chem. 2004, 47, 56.
45. Goddard, W. A.; Kim, S.-K.; Li, Y.; Trzaskowski, B.; Griffith, A. R.; Abrol, R. J. Struct. Biol. 2010, 170, 10.
46. Mapelli, M.; Massimiliano, L.; Crovace, C.; Seeliger, M. A.; Tsai, L.-H.; Meijer, L.; Musacchio, A. J. Med. Chem. 2005, 48, 671.