Design, synthesis and in vitro antitumour activity of new heteroaryl ethylenes

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 221-227

  Fortuna, Cosimo G ^a   Barresi, Vincenza ^a   Bonaccorso, Carmela ^a   Consiglio, Giuseppe ^a   Failla, Salvatore ^a   Trovato Salinaro, Angela ^a   Musumarra, Giuseppe ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Antitumour compounds; Heterocycles; Molecular modelling; QSAR

Indexed keywords

1 METHYL 2 [2 (1 METHYL 1H INDOL 2 YL)VINYL] PYRIDINIUM IODIDE; 1 METHYL 2 [2 (1 METHYL 1H PYRROL 2 YL)VINYL] PYRIDINIUM IODIDE; 1 METHYL 2 [2 (5 PHENYL 2 THIENYL)VINYL]QUINOLINIUM IODIDE; 1 METHYL 4 [2 (1 METHYL 1H PYRROL 2 YL)VINYL] PYRIDINIUM IODIDE; 1,3 DIMETHYL 2 [2 (1 METHYL 1H PYRROL 2 YL)VINYL] 1H IMIDAZOL 3 IUM IODIDE; 2 [ 2 [5' (DIBUTYLAMINO) 2,20 BITHIEN 5 YL]VINYL] 1 METHYLQUINOLINIUM IODIDE; 2 [2 (4 AMINOPHENYL) 1 CYANOVINYL] 1 METHYLPYRIDINIUM IODIDE; 2 [2 (5 CHLORO 2 THIENYL)VINYL] 1 METHYLQUINOLINIUM IODISE; 2 [2 [4 (DIMETHYLAMINO)PHENYL]VINYL] 1 METHYLQUINOLINIUM IODIDE; 2 [2 [5' (DIBUTYLAMINO) 2,2' BITHIEN 5 YL]VINYL] 1 METHYLQUINOLINIUM IODIDE; 2,6 2 [ 2 [5' DIBUTYLAMINO 2,2' BITHIENYL 5 YL] VINYL] 1 METHYLPYRIDINIUM IODIDE; 2,6 2 [2 [4 (DIMETHYLAMINO)PHENYL]VINYL] 1 METHYLPYRIDINIUM IODIDE; 2,6 2 [2 [4 (DIPHENYLAMINO)PHENYL]VINYL] 1 METHYLPYRIDINIUM IODIDE; 2,6 2[ 2 (2,2' BITHIEN 5 YL)VINYL] 1 METHYLPYRIDINIUM IODIDE; 4 [2 [4 (DIMETHYLAMINO)PHENYL]VINYL] 1 METHYLPYRIDINIUM IODIDE; ETHYLENE DERIVATIVE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; HETEROCYCLIC COMPOUND;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CELL LINE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR MODEL; CHEMISTRY; HUMAN; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG DESIGN; ETHYLENES; HETEROCYCLIC COMPOUNDS; HUMANS;

EID: 84855812536     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.060     Document Type: Article

References (41)

1. F.P. Ballistreri, V. Barresi, P. Benedetti, G. Caltabiano, C.G. Fortuna, M.L. Longo, and G. Musumarra Bioorg. Med. Chem. 12 2004 1689 1695
2. P.J. Goodford J. Med. Chem. 28 1985 849 857
3. G. Cruciani, and K.A. Watson J. Med. Chem. 37 1994 2589 2601
4. R.D. Cramer III, D.E. Patterson, and J. Bunce J. Am. Chem. Soc. 110 1988 5959 5967
5. M. Pastor, G. Cruciani, I. McLay, S. Pickett, and S. Clementi J. Med. Chem. 43 2000 3233 3243
6. H. González-Díaz, G. Agüero, M.A. Cabrera, R. Molina, L. Santana, E. Uriarte, G. Delogu, and N. Castañedo Bioorg. Med. Chem. Lett. 15 2005 551 557
7. H. González-Diaz, Y. Marrero, I. Hernandez, I. Bastida, E. Tenorio, O. Nasco, E. Uriarte, N. Castanedo, M.A. Cabrera, E. Aguila, O. Marrero, A. Morales, and M. Perez Chem. Res. Toxicol. 16 2003 1318 1327
8. H. González-Díaz, M. Cruz-Monteagudo, R. Molina, E. Tenorio, and E. Uriarte Bioorg. Med. Chem. 13 2005 1119 1129
9. E. Estrada Mutat. Res. 420 1998 67 75
10. H. González-Díaz, E. Olazábal, L. Santana, E. Uriarte, Y. González-Díaz, and N. Castañedo Bioorg. Med. Chem. 15 2007 962 968
11. H. González-Díaz, L.A. Torres-Gómez, Y. Guevara, M.S. Almeida, R. Molina, N. Castañedo, L. Santana, and E. Uriarte J. Mol. Model. 11 2005 116 123
12. H. González-Díaz, M. Cruz-Monteagudo, R. Molina, E. Tenorio, and E. Uriarte Bioorg. Med. Chem. 13 2005 1523 1530
13. J.I. González Borroto, G. Pérez Machado, A. Creus, and R. Marcos Mutagenesis 20 2005 193 197
14. C.G. Fortuna, V. Barresi, G. Berellini, and G. Musumarra Bioorg. Med. Chem. 16 2008 4150 4159
15. C.G. Fortuna, V. Barresi, and G. Musumarra Bioorg. Med. Chem. 18 2010 4516 4523
16. M. Tarleton, J. Gilbert, M.J. Robertson, A. McCluskey, and J.A. Sakoff Med. Chem. Comm. 2 2011 31 37
17. C.G. Fortuna, C. Bonaccorso, F. Qamarb, A. Anu, I. Ledoux, and G. Musumarra Org. Biomol. Chem. 9 2011 1608 1613
18. E. Carosati, S. Sciabola, and G. Cruciani J. Med. Chem. 47 2004 5114 5125
19. P. Crivori, G. Cruciani, P.A. Carrupt, and B. Testa J. Med. Chem. 43 2000 2204 2216
20. G. Cruciani, M. Meniconi, E. Carosati, I. Zamora, and R. Mannhold H. van de Waterbeemd, H. Lennernäs, P. Artursson, Methods and Principles in Medicinal Chemistry vol. 18 2003 Wiley-VCH Publishers 406 419
21. G. Berellini, G. Cruciani, and R. Mannhold J. Med. Chem. 48 2005 4389 4399
22. R. Mannhold, G. Berellini, E. Carosati, and P. Benedetti G. Cruciani, R. Mannhold, H. Kubinyi, G. Folkers, Molecular Interaction Fields vol. 27 2006 WILEY-VCH Verlag GmbH & Co. KGaA Weinheim 173 196
23. S. Wold, and M. Sjöström B.R. Kowalski, Chemometrics: Theory and Application 1977 ACS Symposium Series Washington 243 282
24. S. Wold, C. Albano, W.J. Dunn III, U. Edlund, K. Esbensen, P. Geladi, S. Hellberg, E. Johansson, W. Lindberg, and M. Sjöström B.R. Kowalski, Chemometrics 1984 17 96
25. www.moldiscovery.com.
26. GRID v. 20 Molecular Discovery Ltd.
27. D.N.A. Boobbyer, P.J. Goodford, P.M. Mcwhinnie, and R.C. Wade J. Med. Chem. 32 1989 1083 1094
28. J.M. Kauffman, and G. Moyna J. Org. Chem. 68 2003 839 853
29. X.H. Zhang, L.Y. Wang, Z.X. Nan, S.H. Tan, and Z.X. Zhang Dyes Pigm. 79 2008 205 209
30. D. Sutherland, and C. Compton J. Org. Chem. 17 1952 1257 1261
31. W.L. Foye, Y.J. Lee, K.A. Shan, and J.M. Kauffman J. Pharm. Sci. 67 1978 962 964
32. C.F. Koelsch J. Am. Chem. Soc. 66 1944 2126
33. A.P. Phillips J. Org. Chem. 14 1949 302 305
34. D. Reefman, J.P. Cornelissen, J.G. Haasnoot, R.A.G. De Graaff, and J. Reedijk Inorg. Chem. 29 1990 3933 3935
35. K. Chanawanno, S. Chantrapromma, T. Anantapong, A. Kanjana-Opas, and H.-K. Fun Eur. J. Med. Chem. 45 2010 4199 4208
36. X. Xu, W. Qiu, Q. Zhou, J. Tang, F. Yang, Z. Sun, and P. Audebert J. Phys. Chem. B. 112 2008 4913 4917
37. E. Marri, U. Mazzucato, C.G. Fortuna, G. Musumarra, and A. Spalletti J. Photochem. Photobiol. A 179 2006 314 319
38. F.P. Ballistreri, V. Barresi, G. Consiglio, C.G. Fortuna, M.L. Longo, and G. Musumarra ARKIVOC 1 2003 105 117
39. G.R. Clemo, and G.A. Swan J. Chem. Soc. 1938 1454 1455
40. A. Facchetti, A. Abbotto, L. Beverina, M.E. van der Boom, P. Dutta, G. Evmenenko, G.A. Pagani, and T.J. Marks Chem. Mater. 15 2003 1064 1072
41. T.J. Mosmann J. Immunol. Meth. 65 1983 55 63