Synthesis, antiproliferative activity and genotoxicity of novel anthracene-containing aminophosphonates and a new anthracene-derived Schiff base

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 1, 2012, Pages 117-124

  Kraicheva, I ^a   Tsacheva, I ^a   Vodenicharova, E ^a   Tashev, E ^a   Tosheva, T ^a   Kril, A ^b   Topashka Ancheva, M ^c   Iliev, I ^b   Gerasimova, Ts ^c   Troev, K ^a  

^a INSTITUTE OF POLYMERS   (Bulgaria)

^b BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

^c INSTITUTE OF BIODIVERSITY AND ECOSYSTEM RESEARCH   (Bulgaria)

Author keywords

Aminophosphonic acids; Antitumor activity; Cytotoxicity; Genotoxicity; NMR; Schiff bases

Indexed keywords

9 ANTHRYLIDENE 4 METHYLANILINE; 9 ANTHRYLIDENE FURFURYLAMINE; [N METHYL(DIETHOXYPHOSPHONYL) 1 (9 ANTHRYL)] 4 METHYLANILINE; [N METHYL(DIETHOXYPHOSPHONYL) 1 (9 ANTHRYL)]FURFURYLAMINE; [N METHYL(DIMETHOXYPHOSPHONYL) 1 (9 ANTHRYL)] 4 METHYLANILINE; DOXORUBICIN; MITOMYCIN C; PHOSPHORAMIDIC ACID DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; CELLULAR DISTRIBUTION; CHROMOSOME ABERRATION; CHROMOSOME DAMAGE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG DOSE COMPARISON; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; GENOTOXICITY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

ANIMALS; ANTHRACENES; ANTINEOPLASTIC AGENTS; CELL LINE; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; NEOPLASMS; PHOSPHONIC ACIDS; SCHIFF BASES;

MUS;

EID: 84855189874     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.11.024     Document Type: Article

References (34)

1. R.A. Cherkasov, and V.I. Galkin Usp. Khim. 67 1998 940
2. F. Orsini, G. Sello, and M. Sisti Curr. Med. Chem. 17 2010 264
3. M. Sienczyk, and J. Oleksyszyn Curr. Med. Chem. 16 2009 1673
4. M. Ordóñez, H. Rojas-Cabrera, and C. Cativiela Tetrahedron 65 2009 17
5. Y.V. Rassukana, P.P. Onys'ko, M.V. Kolotylo, A.D. Sinitsa, P. Łyźwa, and M. Mikołajczyk Tetrahedron Lett. 50 2009 288
6. L. Azema, R. Baron, and S. Ladame Curr. Enzyme Inhib. 2 2006 61
7. P. Kaur, W. Wever, T. Rajale, and G. Li Chem. Biol. Drug Des. 76 2010 314
8. J. Huang, and R. Chen Heteroat. Chem. 11 2000 480
9. J.R. Green Med. Klin. 95 2000 23
10. R. Hirschmann, A.B. Smith III, C.M. Taylor, P.A. Benkovic, S.D. Taylor, K.M. Yager, P.A. Sprengler, and S.J. Benkovic Science 265 1994 234
11. P. Kafarski, and B. Lejczak V.P. Kukhar, H.R. Hudson, Aminophosphonic and Aminophosphinic Acids Chemistry and Biological Activity 2000 John Wiley & Sons Chichester 407 435
12. I.C. Dormehl, W.K.A. Louw, R.J. Milner, E. Kilian, and F.H.A. Schneeweiss Arzneim.-Forsch. 51 2001 258
13. R. Gancarz, and M. Dudek Phosphorus, Sulfur Silicon Relat. Elem. 114 1996 135
14. H. Kleszczyńska, D. Bonarska, J. Sarapuk, and K. Bielecki Z. Naturforsch. 56c 2001 999
15. R. Martinez, and L. Chacon-Garcia Curr. Med. Chem. 12 2005 127
16. G.T. Bowden, R. Roberts, D.S. Alberts, Y.-M. Peng, and D. Garcia Cancer Res. 45 1985 4915
17. H. Prinz, Y. Ishii, T. Hirano, T. Stoiber, J.A. Camacho Gomez, P. Schmidt, H. Düssmann, A.M. Burger, J.H. Prehn, E.G. Günther, E. Unger, and K. Umezawa J. Med. Chem. 46 2003 3382
18. H. Prinz, P. Schmidt, K.J. Böhm, S. Baasner, K. Müller, E. Unger, M. Gerlach, and E.G. Günther J. Med. Chem. 52 2009 1284
19. H. Prinz, P. Schmidt, K.J. Böhm, S. Baasner, K. Müller, M. Gerlach, E.G. Günther, and E. Unger Bioorg. Med. Chem. 19 2011 4183
20. H.C. Nickel, P. Schmidt, K.J. Böhm, S. Baasner, K. Müller, M. Gerlach, E. Unger, E.G. Günther, and H. Prinz Eur. J. Med. Chem. 45 2010 3420
21. U. Herrmann, B. Tümmler, G. Maass, P.K.T. Mew, and F. Vögtle Biochemistry 23 1984 4059
22. B.P. Lugovkin Zh. Obshch. Khim. 45 1975 1277
23. G. Hägele V.P. Kukhar, H.R. Hudson, Aminophosphonic and Aminophosphinic Acids Chemistry and Biological Activity 2000 John Wiley & Sons Chichester 239 243
24. I. Kraicheva Phosphorus, Sulfur Silicon Relat. Elem. 178 2003 191
25. S. Failla, P. Finocchiaro, and G.A. Consiglio Heteroat. Chem. 11 2000 493
26. J. Lewkowski, M. Rzeźniczak, and R. Skowroński Heteroat. Chem. 11 2000 144
27. T. Prot Rocz. Chem. 45 1971 247
28. P.E. Hansen Org. Magn. Reson. 12 1979 109
29. L. Ernst Org. Magn. Reson. 9 1977 35
30. T. Mosmann J. Immunol. Methods 65 1983 55
31. E. Borenfreund, and J.A. Puerner Toxicol. Lett. 24 1985 119
32. http://ecvam-dbalm.jrc.ec.europa.eu/view-doc.cfm?iddoc=666&tdoc=prot.
33. H. Spielmann, M. Balls, J. Dupuis, W.J.W. Pape, G. Pechovitch, O. DeSilva, H.-G. Holzhtter, R. Clothier, P. Desolle, F. Gerberick, M. Liebsch, W.W. Lovell, T. Maurer, U. Pfannenbecker, J.M. Potthast, M. Csato, D. Sladowski, W. Steiling, and P. Brantom Toxicol. In Vitro 12 1998 305
34. R.J. Preston, B.J. Dean, S. Galloway, H. Holden, A.F. McFee, and M. Shelby Mutat. Res. 189 1987 157