Synthesis, antitumor activity and QSAR studies of some 4-aminomethylidene derivatives of edaravone

Bioorganic Chemistry

Volumn 39, Issue 1, 2011, Pages 18-27

  Marković, Violeta ^a   Erić, Slavica ^b   Juranić, Zorica D ^c   Stanojković, Tatjana ^c   Joksović, Ljubinka ^a   Ranković, Branislav ^a   Kosanić, Marijana ^a   Joksović, Milan D ^a  

^a UNIVERSITY OF KRAGUJEVAC   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c INSTITUTE FOR ONCOLOGY AND RADIOLOGY OF SERBIA   (Serbia)

Author keywords

Antitumor activity; Edaravone derivatives; QSAR studies

Indexed keywords

3 METHYL 1 PHENYL 4 [[(1H PYRAZOL 3 YL)AMINO]METHYLIDENE] 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 1 PHENYL 4 [[(5 PHENYL 1H PYRAZOL 3 YL)AMINO]METHYLIDENE] 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 1 PHENYL 4 [[(PYRIDIN 2 YLMETHYL)AMINO]METHYLIDENE] 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 1 PHENYL 4 [[(THIOPHEN 2 YLMETHYL)AMINO]METHYLIDENE] 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 1 PHENYL 4 THIOUREIDOMETHYLIDENE 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(2 METHYLPHENYL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(2 NITROPHENYL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(3 METHYLPHENYL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(3 NITROPHENYL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(4 METHYLPHENYL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(4 NITROPHENYL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 3 METHYL 4 [[(5 METHYL 1H PYRAZOL 3 YL)AMINO]METHYLIDENE] 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 4 [[(4 ETHOXYCARBONYL 1H PYRAZOL 3 YL)AMINO]METHYLIDENE] 3 METHYL 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 4 [[(4 HYDROXYPHENYL)AMINO]METHYLIDENE] 3 METHYL 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 4 [[(4 METHOXY 5 METHYL 1H PYRAZOL 3 YL)AMINO]METHYLIDENE] 3 METHYL 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 4 [[(FURAN 2 YLMETHYL)AMINO]METHYLIDENE] 3 METHYL 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 4 [[[5 (FURAN 2 YL) 1H PYRAZOL 3 YL]AMINO]METHYLIDENE] 3 METHYL 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 5 ONE; 4 AMINOMETHYLIDENE DERIVATIVE; NORPHENAZONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; ANTIPYRINE; BREAST NEOPLASMS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; FREE RADICAL SCAVENGERS; HUMANS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78751647459     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2010.10.003     Document Type: Article

References (21)

1. N. Zhang, M. Komine-Kobayashi, R. Tanaka, M. Liu, Y. Mizuno, and T. Urabe Stroke 36 2005 2220 2225
2. T. Watanabe, M. Tahara, and S. Todo Cardiovasc. Ther. 26 2008 101 114
3. K. Sujatha, G. Shanthi, N. Panneer Selvam, S. Manoharan, P.T. Perumal, and M. Rajendran Bioorg Med. Chem. Lett. 19 2009 4501 4503
4. X. Fan, X. Zhang, L. Zhou, K.A. Keith, E.R. Kern, and P.F. Torrence Bioorg. Med. Chem. Lett. 16 2006 3224 3228
5. D. Castagnolo, F. Manetti, M. Radi, B. Bechi, M. Pagano, A. De Logu, R. Meleddu, M. Saddi, and M. Botta Bioorg Med. Chem. 17 2009 5716 5721
6. R. Tripathy, A. Ghose, J. Singh, E.R. Bacon, T.S. Angeles, S.X. Yang, M.S. Albom, L.D. Aimone, J.L. Herman, and J.P. Mallamo Bioorg. Med. Chem. Lett. 17 2007 1793 1798
7. S. Kokura, N. Yoshida, N. Sakamoto, T. Ishikawa, T. Takagi, H. Higashihara, N. Nakabe, O. Handa, Y. Naito, and T. Yoshikawa Cancer Lett. 229 2005 223 233
8. T. Arai, M. Nonogawa, K. Makino, N. Endo, H. Mori, T. Miyoshi, K. Yamashita, M. Sasada, M. Kakuyama, and K. Fukuda J. Pharmacol. Exp. Ther. 324 2008 529 538
9. Y. Kakiuchi, N. Sasaki, M. Satoh-Masuoka, H. Murofushi, and K. Murakami-Murofushi Biochem. Biophys. Res. Commun. 320 2004 1351 1358
10. P. Pevarello, M.G. Brasca, P. Orsini, G. Traquandi, A. Longo, M. Nesi, F. Orzi, C. Piutti, P. Sansonna, M. Varasi, A. Cameron, A. Vulpetti, F. Roletto, R. Alzani, M. Ciomei, C. Albanese, W. Pastori, A. Marsiglio, E. Pesenti, F. Fiorentini, J.R. Bischoff, and C. Mercurio J. Med. Chem. 48 2005 2944 2956
11. D. Bebbington, H. Binch, J.D. Charrier, S. Everitt, D. Fraysse, J. Golec, D. Kay, R. Knegtel, C. Mak, F. Mazzei, A. Miller, M. Mortimore, M. O' Donnell, S. Patel, F. Pierard, J. Pinder, J. Pollard, S. Ramaya, D. Robinson, A. Rutherford, J. Studley, and J. Westcott Bioorg. Med. Chem. Lett. 19 2009 3586 3592
12. T. Mosmann J. Immunol. Methods 65 1983 55 63
13. M. Ohno, and T. Abe J. Immunol. Methods 145 1991 199 203
14. Spartan '02 for Linux, Wavefunction, Inc. Irvine, CA, 2002.
15. A.R. Katritzky, W.S. Lobanov, M. Karelson Codessa, Reference Manual (version 2.0), Gainesville, FL, 1994, p. 2.
16. P. Liu, and W.H. Long Int. J. Mol. Sci. 10 2009 1978 1998
17. D.J. Wallace, and J.M. Straley J. Org. Chem. 26 1961 3825 3826
18. A.I. Movchan, A.R. Kurbangalieva, O.N. Kataeva, I.A. Litvinov, and G.A. Chmutova Russ. J. Gen. Chem. 73 2003 1130 1136
19. J. Belmar, F.R. Pérez, J. Alderete, and C. Zúñiga J. Braz. Chem. Soc. 16 2005 179 189
20. B.T. Thaker, K.R. Surati, S. Oswal, R.N. Jadeja, and V.K. Gupta Struct. Chem. 18 2007 295 310
21. K.R. Kim, J.L. Kwon, J.S. Kim, Z. No, H.R. Kim, and H.G. Cheon Eur. J. Pharmacol. 528 2005 37 42