Synthesis of monomeric and dimeric acridine compounds as potential therapeutics in Alzheimer and prion diseases

Archiv der Pharmazie

Volumn 342, Issue 12, 2009, Pages 699-709

  Csuk, René ^a   Barthel, Alexander ^a   Raschke, Christian ^a   Kluge, Ralph ^a   Ströhl, Dieter ^a   Trieschmann, Lothar ^b   Böhm, Gerald ^c  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b Scil Proteins Production GmbH   (Germany)

^c IGZ Innovation and Founding Center Würzburg BioMed ZmK   (Germany)

Author keywords

Acridines; Anti Alzheimer; Antiprion; FACS analysis; Quinacrine

Indexed keywords

4 (3 CHLORO 5 METHOXY 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; ACRIDINE DERIVATIVE; AMYLOID BETA PROTEIN; AMYLOID PROTEIN; DIMER; MEPACRINE; MONOMER; N 4 (2 METHOXY 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 (2 NITRO 5 THIOMETHYL 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 (2 TRIFLUOROMETHOXY 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 (2,4 DIFLUORO 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 (4 THIOMETHYL 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 (5 METHOXY 3 NITRO 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 (6 CHLORO 2 METHOXY 9 ACRIDINYL) N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N 4 9 ACRIDINYL N 1,N 1 DIETHYL 1,4 PENTANEDIAMINE; N,N BIS (2 METHOXY 9 ACRIDINYL) 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS (2 METHOXY 9 ACRIDINYL) 1,8 OCTANEDIAMINE; N,N BIS (2 NITRO 5 THIOMETHYL 9 ACRIDINYL) 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS (2 TRIFLUOROMETHOXY 9 ACRIDINYL) 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS (2 TRIFLUOROMETHOXY 9 ACRIDINYL) 1,8 OCTANEDIAMINE; N,N BIS (2,4 DIFLUORO 9 ACRIDINYL) 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS (2,4 DIFLUORO 9 ACRIDINYL) 1,8 DIAMINOOCTANE; N,N BIS (4 THIOMETHYL 9 ACRIDINYL) 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS (6 CHLORO 2 METHOXY 9 ACRIDINYL) 1,4 BIS(3 AMINOPROPYL)PIPERAZINE; N,N BIS (6 CHLORO 2 METHOXY 9 ACRIDINYL) 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS (6 CHLORO 2 METHOXY 9 ACRIDINYL) 1,8 OCTANEDIAMINE; N,N BIS 9 ACRIDINYL 1,8 DIAMINO 3,6 DIOXAOCTANE; N,N BIS 9 ACRIDINYL 1,8 OCTANEDIAMINE; PRION PROTEIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALZHEIMER DISEASE; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE ACTIVATED CELL SORTING; PRION DISEASE; PRIORITY JOURNAL; SUBSTITUTION REACTION;

ACRIDINES; ALZHEIMER DISEASE; AMYLOID BETA-PROTEIN; DIMERIZATION; DRUG EVALUATION, PRECLINICAL; HUMANS; MOLECULAR STRUCTURE; PRION DISEASES; PRIONS;

EID: 73449111929     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.200900065     Document Type: Article

References (26)

1. M. Citron, Nat. Rev. Neurosci. 2004, 5, 677-685.
2. B. Zhao, M. Yu, M. Neitzel, J. Marugg, et al., J. Biol. Chem. 2008, 238, 2927-2938.
3. Y. Nakagami, S. Nishimura, T. Murasugi, I. Kaneko, et al., Brit. J. Pharmacol. 2002, 137, 676-682.
4. A. Aguzzi, M. Heikenwalder, Nature 2003, 423, 127-129.
5. C. Korth, B. C. H. May, F. E. Cohen, S. B. Prusiner, Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 9836-9841.
6. C. Ryou, G. Legname, D. Peretz, J. C. Craig, et al., Lab. Invest. 2003, 83, 837-843.
7. S. Turnbull, B. J. Tabner, D. R. Brown, D. Allsop, Neuroreport 2003, 14, 1743-1745.
8. M. Vogtherr, S. Grimme, B. Elshorst, D. M. Jacobs, et al., J. Med. Chem. 2003, 46, 3563-3564.
9. B. C. H. May, A. T. Fafarman, S. B. Hong, M. Rogers, et al., Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 3416-3421.
10. R. Csuk, A. Barthel, C. Raschke, Tetrahedron 2004, 60, 5737-5750.
11. J. Hassan, M. Sevigon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469.
12. A. N. Santos, S. Torkler, D. Nowak, C. Schlittig, et al., J. Alzheimer Dis. 2007, 11, 117-125.
13. L. Trieschmann, A. N. Santos, K. Kaschig, S. Torkler, et al., BMC Biotechnol. 2005, 5, 26.
14. H. T. Thi, C.-Y. Lee, K. Teruya, W.-Y. Ong, et al., Bioorg. Med. Chem. 2008, 16, 6737-6746.
15. J. Collinge, M. Gorham, T. Hudson, A. Kennedy, et al., Lancet Neurol. 2009, 8, 334-344.
16. J. Hosokawa-Muto, Y. Kamatari, H. K. Nakamura, K. Kuwata, Antimicrob. Agents Chemother. 2009, 53, 765-771.
17. J. Lim, N. Stock, R. Pracitto, J. K. Boueres, et al., Bioorg. Med. Chem. Lett. 2004, 14, 1913-1916.
18. E. R. Shepard, H. A. Shonle, J. Am. Chem. Soc. 1948, 70, 1979-1980.
19. S. Girault, P. Grellier, A. Berecibar, L. Maes, et al., J. Med. Chem. 2000, 43, 2646-2654.
20. E. S. Canellakis, Y. H. Shaw, W. E. Hanners, R. A. Schwartz, Biochim. Biophys. Acta 1976, 418, 277-289.
21. A. K. Singh, Chem. Pharm. Bull. 1975, 23, 1869-1873.
22. L. P. G. Wakelin, M. Romanos, T. K. Chen, D. Glaubiger, et al., Biochemistry 1978, 17, 5057-5063.
23. T. K. Chen, R. Fico, E. S. Canellakis, J. Med. Chem. 1978, 21, 868-874.
24. R. M. Acheson, E. C. Constable, R. G. Wright, G. N. Taylor, J. Chem. Res. 1983, 1, 101-132.
25. J. Markovits, C. Garbay-Jaureguiberry, B. P. Roques, J. Le Pecq, Eur. J. Biochem. 1989, 180, 359-366.
26. W. A. Denny, G. J. Atwell, B. C. Baguley, L. P. G. Wakelin, J. Med. Chem. 1985, 18, 1568-1574.