Synthesis and biological evaluation of modified acridines: the effect of N- and O- substituent in the nitrogenated ring on antitumor activity

European Journal of Medicinal Chemistry

Volumn 41, Issue 3, 2006, Pages 340-352

  Sánchez, Isabel ^a   Reches, Rosa ^a   Caignard, Daniel Henry ^b   Renard, Pierre ^b   Pujol, Maria Dolors ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

Acridines; Antitumor agents; Cytotoxicity; Polycyclic systems

Indexed keywords

11 (3 CHLOROPHENYLAMINO) 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 11 (3,4,5 TRIMETHOXYBENZYLOXY) 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 11 (4 FLUOROPHENOXY) 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 11 (ADENOSIN 5' TRIPHOSPHATE) 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 11 (ADENOSIN 5' TRIPHOSPHATE) 9 BROMO 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 11 [2 (DIETHYL)ETHYLENDIAMINE] 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 11 [2 (DIMETHYL)ETHYLENDIAMINE] 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 12 [(2 DIMETHYL)ETHYLENDIAMINO] 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; 6 (N,N DIETHYLAMINOETHYL) 6,9 DIHYDRO 5H DIOXINO[2,3 I]PYRIDO[4,2,3 KL]ACRIDINE; 6,9 DIHYDRO 5H DIOXINO[2,3 I]PYRIDO[4,2,3 KL]ACRIDINE; 9 NITRO 11 [2 (DIETHYL)ETHYLENDIAMINE] 2,3 DIHYDRO 1,4 DIOXINO[2,3 B]ACRIDINE; ACRIDINE DERIVATIVE; AMSACRINE; DIOXINOACRIDINE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; NITROGEN; OXYGEN;

ACIDITY; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL PROLIFERATION; CYCLIZATION; CYTOTOXICITY; DEHYDRATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; IC 50; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ACRIDINES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NITROGEN; OXYGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646014783     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2005.11.006     Document Type: Article

References (23)

1. Gamage S.A., Tepsiri N., Wilairat P., Wojcik S.J., Figgit D.P., Ralph R., and Denny W.A. J. Med. Chem. 37 (1994) 1486-1494
2. Gamage S.A., Figgit D.P., Wojcik S.J., Ralph R., Ransijn A., and Mauel J. J. Med. Chem. 40 (1997) 2634-2642
3. Mauel J., Denny W.A., Gamage S.A., Ransijn A., Wojcik S.L., Figgit D.P., and Palph R. Antimicrob. Agents Chemother. 37 (1993) 991-996
4. a) B.F. Cain, G.J. Atwell, W.A. Denny, J. Med. Chem. 18 (1975) 1110-1117. b) W.A. Denny, B.C. Baguley, Current Topic. In Med. Chem. 3 (2003) 339-353. c) W.A. Denny, Cur. Med. Chem. 9 (2002) 1655-1665. d) J.-P. Galy, S. Morel, G. Boyer, J. Elguero, J. Heterocyclic Chem. 33 (1996) 1551-1560. e) M. Kimura, I. Okabayashi, A. Kato, J. Heterocyclic Chem. 30 (1993) 1101-1104. f) F. Chatel, S. Morel, G. Boyer, J.P. Galy, Heterocycles 53 (2000) 2535-2552.
5. a) H.H. Lee, W.R. Wilson, D.M. Ferry, P. VanZijl, S.M. Pullen, W.A. Denny, J. Med. Chem. 39 (1996) 2508-2517. b) M. Gniazdwowski, M. Szmigiero, L, Gen. Pharmacol. 26 (1995) 473-481.
6. a) B.F. Cain, G.J. Atwell, W.A. Denny, J. Med. Chem. 19 (1976) 772-777. b) M. Kimura, I. Okabayashi, A. Kato, Chem. Pharm. Bull. (Tokyo) 37 (1989) 697-701.
7. a) G. Atwell, G.W. Rewcastle, B.C. Baguley, W.A. Denny, J. Med. Chem. 30 (1987) 664-669. b) I. Antonini, P. Polucci, T.C. Jenkins, L.R. Kelland, E. Menta, N. Pescalli, B. Stefanska, J. Maserski, S. Martelli, J. Med. Chem. 40 (1997) 3749-3755. c) L.W. Deady, J. Desneves, A.J. Kaye, M. Thompson, G.J. Finlay, B.C. Baguley, W.A. Denny, Bioorg. Med. Chem. 7 (1999) 2801-2809.
8. Jain S.C., Bhandary K.K., and Sobell H.M. J. Mol. Biol. 135 (1979) 813-840
9. Neidle S., Achari A., Taylor G.C., Berman H.M., Carrell H.L., Glusker J.P., and Stallings W.C. Nature 269 (1977) 304-307
10. Kennard O., and Hunter W.N. Chem. Int. Ed. Engl. 30 (1991) 1254-1277
11. Antonini I., Polucci P., Kelland L.R., Spinelli S., Pescalli N., and Martelli S. J. Med. Chem. 43 (2000) 4801-4805
12. a) N.T. Coon, A.S. Higashi. Research Laboratory. http://mayoresearch.mayo.edu /mayo/research. b) D.S. Martin, D. Fung. Cancer Res. 60 (2000) 6776-6783. c) L.R. Dearth, R.K. Brachmann, Cancer Biol. Ther. 3 (2004) 638-640. d) X.L. Zu, M. Guppy, Biochem. Biophys. Res. 231 (2004) 459-465. e) L.J. Warnock, S.A. Raines, Cancer Biol. Ther. 3 (2004) 633-636.
13. Pellon R.F., Mamposo T., Carrasco R., and Rodés L. Synt. Commun. 26 (1996) 3877-3883
14. Barbe J., Boyer G., Carignano I., Elguero J., Galy J.-P., Morel S., and Oughedani R. Tetrahedron Lett. 32 (1991) 6709-6710
15. Pujol M.D., Rosell G., and Guillaumet G. Eur. J. Med. Chem. 31 (1996) 889-894
16. Bourlot A.S., Sánchez I., Dureng G., Guillaumet G., Massingham R., Monteil A., Winslow E., Pujol M.D., and Mérour J.-Y. J. Med. Chem. 41 (1998) 3142-3158
17. a) N. Fixler, M. Demeunynck, J. Lhome, Synth. Commun. 27 (1997) 2311-2324. b) J. Stanslas, D.J. Hagan, M.J. Ellis, C. Turner, J. Carmichael, W. Ward, T. R. Hammonds, M.F.G. Stevens, J. Med. Chem. 43 (2000) 1563-1572.
18. Vorbrüggen H. Synthesis (Mass.) (1973) 301-302
19. a) E. Melliou, P. Magiatis, S. Mitaku, A.-L. Skaltsounis, A. Pierré, G. Atassi, P. Renard, Bioorg. & Med. Chem. 9 (2001) 607-612. b) J.M. Wu, F. Shan, G.S. Wu, Y. Li, J. Ding, D. Xiao, J. X. Han, G. Atassi, S. Léonce, D.H. Caignard, P. Renard, Eur. J. Med. Chem. 36 (2001) 469-479. c) A. Pierré, T.A. Dunn, L. Kraus-Berthier, S. Léonce, D. Saint-Dizier, G. Regnier, A. Dhainaut, J.P. Bizzari, G. Atassi, I. Invest. New Drugs 10 (1992) 137-141.
20. a) A. Bermejo, I. Andreu, F. Suvire, S. Léonce, D.H. Caignard, P. Renard, A. Pierre, R.D. Enriz, D. Cortés, N. Cabedo, J. Med. Chem. 45 (2002) 5058-5068.
21. Owa T., Yoshino H., Yoshimatsu K., Ozawa Y., Sugi N.H., Nagasu Y., Koyanagi N., and Kitoh K. J. Med. Chem. 42 (1999) 3789-3799
22. a) S. Morel, J.P. Galy, R. Faure, Magn. Reson. Chem. 35 (1997) 556-560. b) M. Robin, J.P. Galy, R. Faure, Magn. Reson. Chem. 39 (2001) 225-228.
23. Wakelin L.P.G., Adams A., and Denny W.A. J. Med. Chem. 45 (2002) 894-901