Synthesis and biophysical evaluation of arylhydrazono-1H-2-indolinones as β-amyloid aggregation inhibitors

European Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2011, Pages 275-284

  Campagna, Francesco ^a   Catto, Marco ^a   Purgatorio, Rosa ^a   Altomare, Cosimo D ^a   Carotti, Angelo ^a   De Stradis, Angelo ^a   Palazzo, Gerardo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Amyloid aggregation inhibitors; Alzheimer's disease; Isatin 3 arylhydrazones

Indexed keywords

1H INDOLE 2,3 DIONE 3 [(3 CHLOROPHENYL)HYDRAZONE; 1H INDOLE 2,3 DIONE 3 [(3 FLUOROPHENYL)HYDRAZONE; 1H INDOLE 2,3 DIONE 3 [(4 CHLOROPHENYL)HYDRAZONE; 1H INDOLE 2,3 DIONE 3 [(4 ISOPROPYLPHENYL)HYDRAZONE]; 1H INDOLE 2,3 DIONE 3 [(4 METHOXYPHENYL)HYDRAZONE]; 3 ARYLHYDRAZONOINDOLIN 2 ONE DERIVATIVE; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(3 CHLOROPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(3 TERT BUTYLPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(4 CHLOROPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(4 ISOPROPYLPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(4 METHOXYPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(4 METHYLPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [(4 TERT BUTYLPHENYL)HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [[3 (BENZYLOXY)PHENYL]HYDRAZONE]; 5 METHOXY 1H INDOLE 2,3 DIONE 3 [[4 (BENZYLOXY)PHENYL]HYDRAZONE]; 5,6 DIHYDROXY 1H INDOLE 2,3 DIONE 3 [(3 CHLOROPHENYL)HYDRAZONE]; 5,6 DIMETHOXY 1H INDOLE 2,3 DIONE 3 (PHENYLHYDRAZONE); 5,6 DIMETHOXY 1H INDOLE 2,3 DIONE 3 [(2 CHLOROPHENYL)HYDRAZONE]; 5,6 DIMETHOXY 1H INDOLE 2,3 DIONE 3 [(4 CHLOROPHENYL)HYDRAZONE]; 6 METHOXY 1H INDOLE 2,3 DIONE 3 (PHENYLHYDRAZONE); 6 METHOXY 1H INDOLE 2,3 DIONE 3 [(4 ISOPROPYLPHENYL)HYDRAZONE]; AMYLOID; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; ARYLHYDRAZONO 1H 2 INDOLINONE DERIVATIVE; ARYLHYDRAZONO INDOLIN 2 ONE DERIVATIVE; INDOLE DERIVATIVE; ISATIN 3 ARYLHYDRAZONE DERIVATIVE; PHENYLHYDRAZONE DERIVATIVE; THIOFLAVINE; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; DRUG SCREENING; DRUG SYNTHESIS; FLUORESCENCE ANALYSIS; IC 50; LIGHT SCATTERING; PROTEIN CONFORMATION; PROTEIN POLYMERIZATION; STRUCTURE ACTIVITY RELATION; TRANSMISSION ELECTRON MICROSCOPY;

AMYLOID BETA-PEPTIDES; CIRCULAR DICHROISM; DRUG EVALUATION, PRECLINICAL; INDOLES; KINETICS; PEPTIDE FRAGMENTS; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 78650516737     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.11.015     Document Type: Article

References (47)

1. F. Chiti, and C.M. Dobson Annu. Rev. Biochem. 75 2006 333 366
2. M. Bartolini, and V. Andrisano ChemBioChem 11 2010 1018 1035
3. J.C. Rochet, and P.T. Lansbury Curr. Opin. Struct. Biol. 10 2000 60 68
4. J.D. Horper, and P.T. Lansbury Ann. Rev. Biochem. 66 1997 385 407
5. M. Frändrich Cell. Molec. Life Sci. 64 2007 2066 2078
6. M. Necula, R. Kayed, S. Milton, and C.C. Glabe J. Biol. Chem. 282 2007 10311 10324
7. C.C. Glabe Subcell. Biochem. 38 2005 167 177
8. H. Levine III Amyloid 14 2007 185 197
9. M. Török, M. Abid, S.C. Mhadgut, and B. Török Biochemistry 45 2006 5377 5383
10. M. Pappolla, P. Bozner, C. Soto, H. Shao, N.K. Robakisi, M. Zagorski, B. Frangione, and J. Ghiso J. Biol. Chem. 273 1998 7185 7188
11. T. Cohen, A. Frydman-Marom, M. Rechter, and E. Gazit Biochemistry 45 2006 4727 4735
12. C. Rivire, T. Richard, X. Vitrac, J.M. Mérillon, J. Valls, and J.P. Monti Bioorg. Med. Chem. Lett. 18 2008 828 831
13. Y. Porat, A. Abramowitz, and E. Gazit Chem. Biol. Drug Des 67 2006 27 37
14. K. Ono, K. Hasegawa, H. Naiki, and M. Yamada Biochim. Biophys. Acta 1690 2004 193 202
15. C. Rivire, T. Richard, L. Quentin, S. Krisa, J.M. Mérillon, and J.P. Monti Bioorg. Med. Chem. 15 2007 1160 1167
16. J. Gsponer, U. Haberthur, and A. Caflisch Proc. Natl. Acad. Sci. USA 100 2003 5154 5159
17. D.K. Klimov, and D. Thirumalai Structure 11 2003 295 307
18. R.D. Hills Jr., and C.L. Brooks III J. Mol. Biol. 368 2007 894 901
19. M. Convertino, R. Pellarin, M. Catto, A. Carotti, and A. Caflisch Protein Sci. 18 2009 792 800
20. E. Gazit FASEB J. 16 2002 77 83
21. E. Gazit Bioinformatics 18 2002 880 883
22. E. Gazit Drugs Future 29 2004 613 616
23. G.B. McGaughey, M. Gagné, and A.K. Rappé J. Biol. Chem. 273 1998 15458 15463
24. Y. Porat, Y. Mazor, S. Efrat, and E. Gazit Biochemistry 43 2004 14454 14462
25. J. Zheng, B. Ma, and R. Nussinov Phys. Biol. 3 2006 1 4
26. S. Cellamare, A. Stefanachi, D.A. Stolfa, T. Basile, M. Catto, F. Campagna, E. Sotelo, P. Acquafredda, and A. Carotti Bioorg. Med. Chem. 16 2008 4810 4822
27. M. Catto, R. Aliano, A. Carotti, S. Cellamare, F. Palluotto, R. Purgatorio, A. De Stradis, and F. Campagna Eur. J. Med. Chem. 45 2010 1359 1366
28. F.D. Popp J. Med. Chem. 12 1969 182 184
29. H.N. Bramson, J. Corona, S.T. Davis, S.H. Dickerson, M. Edelstein, S.V. Frye, R.T. Gampe Jr., P.A. Harris, A. Hassell, W.D. Holmes, R.N. Hunter, K.E. Lackey, B. Lovejoy, M.J. Luzzio, V. Montana, W.J. Rocque, D. Rusnak, L. Shewchuk, J.M. Veal, D.H. Walker, and L.F. Kuyper J. Med. Chem. 44 2001 4339 4358
30. H.R. Lawrence, R. Pireddu, L. Chen, Y. Luo, S.-S. Sung, A.M. Szymanski, M.L.R. Yip, W.C. Guida, S.M. Sebti, J. Wu, and N.J. Lawrence J. Med. Chem. 51 2008 4948 4956
31. S.S. Konstantinović, A. Kapor, B.C. Radovanović, and A. Deak Chem. Ind. Chem. Engin. Q. 14 2008 27 34
32. C.J. Barrow, and M.G. Zagorski Science 253 1991 179 182
33. K.H. Lim, H.H. Collver, Y.T.H. Le, P. Nagchowdhuri, and J.M. Kenney Biochem. Biophys. Res. Comm. 353 2007 443 449
34. D.M. Walsh, A. Lomakin, G.B. Benedek, M.M. Condrom, and D.B. Teplow J. Biol. Chem. 272 1997 22364 22372
35. F. Palluotto, F. Campagna, A. Carotti, M. Ferappi, A. Rosato, and C. Vitali Farmaco 57 2002 63 69
36. T. Sandmeyer Helv. Chim. Acta 2 1919 234 242
37. F.A. Snavely J. Org. Chem. 46 1981 2764 2766
38. S.K. Sridhar, M. Saravanan, and A. Ramesh Eur. J. Med. Chem. 36 2001 615 625
39. J. Halberkann Berichte 54B 1921 3079 3090
40. H.M.M. Bastiaans, G. Donn, N. Knittel, A. Martelletti, R. Rees, M. Schwall, R. Whitford, PCT Int. Appl. 2005107466 A1, 2005.
41. E.H. Vickery, F.L. Pahler, and J.E. Eisenbraun J. Org. Chem. 44 1979 4444 4446
42. A. Lomakin, D.S. Chung, G.B. Benedek, D.A. Kirschner, and D.B. Teplow Proc. Natl. Acad. Sci. USA 93 1996 1125 1129
43. Y. Kusumoto, A. Lomakin, D.B. Teplow, and G.B. Benedek Proc. Natl. Acad. Sci. USA 95 1998 12277 12282
44. I.K. Booker-Milburn, I.R. Dunkin, F.C. Kelly, A.I. Khalaf, D.A. Learmonth, G.R. Proctor, and D.I.C. Scopes J. Chem. Soc. Perkin Trans. 1 1997 3261 3273
45. A. Taylor J. Chem. Res. 1980 4154 4171
46. R. Peters, Y. Georgalis, and W. Saenger Acta Crystallogr. D 54 1998 873 877
47. Zetasizer Nano User Manual 0.317 2007 Malvern Instruments Ltd England