Discovery of oxime-bearing naphthalene derivatives as a novel structural type of Nrf2 activators

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 13, 2015, Pages 3852-3859

  Chang, Ken Ming ^a   Liang, Fong Pin ^b   Chen, I Li ^c   Yang, Shyh Chyun ^a   Juang, Shin Hun ^b,d   Wang, Tai Chi ^c   Chen, Yeh Long ^a   Tzeng, Cherng Chyi ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

^c TAJEN UNIVERSITY   (Taiwan)

^d CHINA MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

Author keywords

Antiproliferative activities; Chemoprevention; Nrf2 activation; Oxime bearing naphthalene derivatives

Indexed keywords

1 (2,5 DIMETHOXYPHENYL) 2 (NAPHTHALEN 1 YLOXY) ETHANONE OXIME; 1 (2,5 DIMETHOXYPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE; 1 (2,5 DIMETHOXYPHENYL) 2 (NAPHTHALEN 2 YLOXY)ETHANONE; 1 (3,4 DIFLUOROPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE; 1 (3,4 DIFLUOROPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE OXIME; 1 (3,4 DIFLUOROPHENYL) 2 (NAPHTHALEN 2 YLOXY)ETHANONE; 1 (4 BROMOPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE OXIME; 1 (4 CHLOROPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE OXIME; 1 (4 FLUOROPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE OXIME; 1 (4 FLUOROPHENYL) 2 (NAPHTHALEN 2 YLOXY)ETHANONE OXIME; 1 (4 METHOXYPHENYL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE OXIME; 1 (BIPHENYL 4 YL) 2 (NAPHTHALEN 1 YLOXY)ETHANONE OXIME; 1 (NAPHTHALEN 1 YLOXY)PROPAN 2 ONE OXIME; 1 (NAPHTHALEN 2 YLOXY)PROPAN 2 ONE OXIME; 2 (NAPHTHALEN 1 YLOXY) 1 (4 (TRIFLUOROMETHYL)PHENYL) ETHANONE OXIME; 2 (NAPHTHALEN 1 YLOXY) 1 (NAPHTHALEN 2 YL)ETHANONE; 2 (NAPHTHALEN 1 YLOXY) 1 (NAPHTHALEN 2 YL)ETHANONE OXIME; 2 (NAPHTHALEN 1 YLOXY) 1 PHENYLETHANONE OXIME; 2 (NAPHTHALEN 1 YLOXY) 1 [4 (TRIFLUOROMETHYL)PHENYL]ETHANONE; 2 (NAPHTHALEN 2 YLOXY) 1 PHENYLETHANONE OXIME; ANTINEOPLASTIC AGENT; LUCIFERASE; METHYL GROUP; NAPHTHALENE DERIVATIVE; OXIME DERIVATIVE; PHENYL GROUP; SERINE; TERT BUTYLHYDROQUINONE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; UNINDEXED DRUG; HYDROGEN PEROXIDE; NFE2L2 PROTEIN, HUMAN; OXIME;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT RESPONSIVE ELEMENT; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL LINE; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOPROPHYLAXIS; DRUG POTENCY; DRUG RESEARCH; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC50; ISOMER; MOLECULAR MECHANICS; PROTEIN PHOSPHORYLATION; STRUCTURE ANALYSIS; TRANSCRIPTION INITIATION; AGONISTS; ANTAGONISTS AND INHIBITORS; CELL SURVIVAL; DRUG DEVELOPMENT; DRUG EFFECTS; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; OXIDATIVE STRESS; PHOSPHORYLATION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG DISCOVERY; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; HYDROGEN PEROXIDE; NAPHTHALENES; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; OXIMES; PHOSPHORYLATION; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84937393187     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.03.046     Document Type: Article

References (24)

1. J.D. Yager, and N.E. Davidson N. Eng. J. Med. 354 2006 270
2. J.W. Kim, I. Tchernyshyov, G.L. Semenza, and C.V. Dang Cell Metab. 3 2006 177
3. C.V. Rao, and B.S. Reddy Curr. Cancer Drug Targets 4 2004 29
4. D. Amakye, Z. Jagani, and M. Dorsch Nat. Med. 19 2013 1410
5. M.B. Sporn, and K.T. Liby Nat. Rev. Cancer 12 2012 564
6. S.K. Niture, J.W. Kaspar, J. Shen, and A.K. Jaiswal Toxicol. Appl. Pharm. 244 2010 37
7. J. Adams, P. Huang, and D. Patrick Biology 6 2002 486
8. S. Singh, S. Vrishni, B.K. Singh, I. Rahman, and P. Kakkar Free Radical Res. 44 2010 1267
9. K.A. Walker, M.B. Wallach, and D.R. Hirschfeld J. Med. Chem. 24 1981 67
10. D. Nardi, A. Tajana, A. Leonardi, R. Pennini, F. Portioli, M.J. Magistretti, and A. Subissi J. Med. Chem. 24 1981 727
11. A. Karakurt, M.A. Alagöz, B. Sayoglu, U. ÇalIs, and S. Dalkara Eur. J. Med. Chem. 57 2012 275
12. C.C. Tzeng, K.H. Lee, T.C. Wang, C.H. Han, and Y.L. Chen Pharm. Res. 17 2000 715
13. Y.L. Chen, T.C. Wang, N.C. Chang, Y.L. Chang, C.M. Teng, and C.C. Tzeng Chem. Pharm. Bull. 46 1998 962
14. T.C. Wang, K.H. Lee, Y.L. Chen, S.S. Liou, and C.C. Tzeng Bioorg. Med. Chem. Lett. 8 1998 2773
15. T.C. Wang, I.L. Chen, P.J. Lu, C.H. Wong, C.H. Liao, K.C. Tsiao, K.M. Chang, Y.L. Chen, and C.C. Tzeng Bioorg. Med. Chem. 13 2005 6045
16. L.C. Chen, S.H. Juang, K.M. Chang, C.C. Tzeng, J.J. Chen, I.L. Chen, and T.C. Wang Chem. Pharm. Bull. 62 2014 106
17. I.-L. Chen, J.-Y. Chen, P.-C. Shieh, J.-J. Chen, and C.-H. Lee Bioorg. Med. Chem. 16 2008 7639
18. I.-L. Chen, J.-J. Chen, Y.-C. Lin, C.-T. Peng, S.-H. Juang, and T.-C. Wang Eur. J. Med. Chem. 59 2013 227
19. X.J. Wang, J.D. Hayes, and C.R. Wolf Cancer Res. 66 2006 10983
20. 13C NMR Spectrometry N. Rose, Spectrometric Identification of Organic Compounds 6th ed. 1998 John Wiley and Sons New York 217 249
21. B.Y. Shin, S.H. Jin, I.J. Cho, and S.H. Ki Free Radical Biol. Med. 53 2012 834
22. Q. Cheng, J.L. Kalabus, J. Zhang, and J.G. Blanco Biochem. Pharm. 83 2012 139
23. K.W. Kang, M.K. Cho, C.H. Lee, and S.G. Kim Mol. Pharm. 59 2001 1147
24. H.C. Huang, T. Nguyen, and C.B. Pickett J. Biol. Chem. 277 2002 42769