Design, synthesis, and evaluation of (E)-N-substituted benzylidene-aniline derivatives as tyrosinase inhibitors

European Journal of Medicinal Chemistry

Volumn 57, Issue , 2012, Pages 383-390

  Bae, Sung Jin ^a   Ha, Young Mi ^a   Park, Yun Jung ^a   Park, Ji Young ^a   Song, Yu Min ^a   Ha, Tae Kwun ^b   Chun, Pusoon ^c   Moon, Hyung Ryong ^a   Chung, Hae Young ^a  

^a Pusan National University   (South Korea)

^b Inje University College of Medicine   (South Korea)

^c Inje University   (South Korea)

Author keywords

(E) 4 ((4 Hydroxyphenylimino)methyl)benzene 1,2 diol; Aniline derivatives; Hyperpigmentation; Tyrosinase inhibitor

Indexed keywords

ETHENESULFONIC ACID ESTER DERIVATIVE; ETHYL 2 [4 [4 [4 (4 FLUOROPHENYL)THIAZOL 2 YLAMINO]BUTOXY]PHENYL]ETHENESULFONATE; ETHYL 2 [4 [4 [4 (THIOPHEN 2 YL)THIAZOL 2 YLAMINO]BUTOXY]PHENYL]ETHANESULFONATE; NON RECEPTOR PROTEIN TYROSINE PHOSPHATASE 2; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROPHOBICITY; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 84870058327     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.09.026     Document Type: Article

References (35)

1. R.A. Spritz, and V.J. Hearing Jr. Adv. Hum. Genet. 22 1994 1 45
2. J.M. Menter, and I. Willis Pigment Cell. Res. 10 1997 214 217
3. S. Holme, K. Malinovsky, and D.L. Roberts Clin. Exp. Dermatol. 26 2001 484 489
4. S. Briganti, E. Camera, and M. Picardo Pigment Cell. Res. 16 2003 101 110
5. E. Greggio, E. Bergantino, D. Carter, R. Ahmad, G.E. Costin, V.J. Hearing, J. Clarimon, A. Singleton, J. Eerola, O. Hellstrom, P.J. Tienari, D.W. Miller, A. Beilina, L. Bubacco, and M.R. Cookson J. Neurochem. 93 2005 246 256
6. I. Kubo, I. Kinst-Hori, K. Nihei, F. Soria, M. Takasaki, J.S. Calderón, and C.L. Céspedes Z. Naturforsch C 58 2003 719 725
7. F. Artés, M. Castañer, and M.I. Gil J. Agric. Food Chem. 4 1998 377 389
8. S. Parvez, M. Kang, H.S. Chung, and H. Bae Phytother. Res. 21 2007 805 816
9. Y.L. Shi, I.F. Benzie, and J.A. Buswell Life Sci. 70 2002 1595 1608
10. T. Kobayashi, W.D. Vieira, B. Potterf, C. Sakai, and G. Imokawa J. Cell. Sci. 108 1995 2301 2309
11. L.G. Fenoll, J.N. Rodríguez-López, F. García- Sevilla, P.A. García-Ruiz, R. Varón, F. García- Cánovas, and J. Tudela Biochim. Biophys. Acta 1548 2001 1 22
12. V.J. Hearing, and K. Tsukamoto FASEB J. 5 1991 2902 2909
13. M. Fairhead, and L. Thony-Meyer N. Biotechnol. 29 2012 183 191
14. G.M. Casañola-Martín, Y. Marrero-Ponce, M.T. Khan, A. Ather, K.M. Khan, F. Torrens, and R. Rotondo Eur. J. Med. Chem. 42 2007 1370 1381
15. K.M. Khan, G.M. Maharvi, M.T. Khan, A. Jabbar Shaikh, S. Perveen, S. Begum, and M.I. Choudhary Bioorg. Med. Chem. 14 2006 344 351
16. K.M. Khan, G.M. Maharvi, M.T. Khan, S. Perveen, M.I. Choudhary, and Atta-Ur-Rahman Mol. Divers. 9 2005 15 26
17. M.T. Khan, M.I. Choudhary, K.M. Khan, M. Rani, and Atta-ur-Rahman Bioorg. Med. Chem. 13 2005 3385 3395
18. T. Shahzadi, M.A. Abbasi, A.U. Rehman, T. Riaz, K.M. Khan, V.U. Ahmad, M. Ashraf, B. Hussain, and M. Ajaib J. Chem. Soc. Pak. 34 2012 442 447
19. K.M. Khan, G.M. Maharvi, S. Perveen, M.T. Khan, R.J. Abdel-Jalil, S.T. Shah, M. Fecker, M.I. Choudhary, Atta-ur-Rahman, and W. Voelter Chem. Biodivers. 2 2005 470 476
20. A. Karioti, A. Protopappa, N. Megoulas, and H. Skaltsa Bioorg. Med. Chem. 15 2007 2708 2714
21. S. Okombi, D. Rival, S. Bonnet, A.M. Mariotte, E. Perrier, and A. Boumendjel Bioorg. Med. Chem. Lett. 16 2006 2252 2255
22. G. Tocco, A. Fais, G. Meli, M. Begala, G. Podda, M.B. Fadda, M. Corda, O.A. Attanasi, P. Filippone, and S. Berretta Bioorg. Med. Chem. Lett. 19 2009 36 39
23. H. Satooka, and I. Kubo Bioorg. Med. Chem. 20 2012 1090 1099
24. S. Song, H.J. Lee, Y. Jin, Y.M. Ha, S.J. Bae, H.Y. Chung, and H. Suh Bioorg. Med. Chem. Lett. 17 2007 461 464
25. Y.M. Ha, S.W. Chung, S. Song, H. Lee, H. Suh, and H.Y. Chung Biol. Pharm. Bull. 30 2007 1711 1715
26. J.H. Choi, S.J. Bae, Y.M. Ha, J.K. No b, E.K. Lee, J.S. Lee, S. Song, H. Lee, H. Suh, B.P. Yu, and H.Y. Chung Bioorg. Med. Chem. Lett. 20 2010 4882 4884
27. J.K. No, D.Y. Soung, Y.J. Kim, K.H. Shim, Y.S. Jun, S.H. Rhee, T. Yokozawa, and H.Y. Chung Life Sci. 65 1999 241 246
28. V. Kahn Pigment Cell. Res. 8 1995 234 240
29. Z.Y. Du, Y.F. Jiang, Z.K. Tang, R.Q. Mo, G.H. Xue, Y.J. Lu, X. Zheng, C.Z. Dong, and K. Zhang Biosci. Biotechnol. Biochem. 75 2011 2351 2358
30. Y.S. Baek, Y.B. Ryu, M.J. Curtis-Long, T.J. Ha, R. Rengasamy, M.S. Yang, and K.H. Park Bioorg. Med. Chem. 17 2009 35 41
31. K.K. Song, H. Huang, P. Han, C.L. Zhang, Y. Shi, and Q.X. Chen Biochem. Biophys. Res. Commun. 342 2006 1147 1151
32. Y.M. Ha, Y.J. Park, J.A. Kim, D. Park, J.Y. Park, H.J. Lee, J.Y. Lee, H.R. Moon, and H.Y. Chung Eur. J. Med. Chem. 49 2012 245 252
33. Y.K. Han, Y.J. Park, Y.M. Ha, D. Park, J.Y. Lee, N. Lee, J.H. Yoon, H.R. Moon, and H.Y. Chung Biochim. Biophys. Acta 1820 2012 542 549
34. Y.M. Ha, Y.J. Park, J.Y. Lee, D. Park, Y.J. Choi, E.K. Lee, J.M. Kim, J.A. Kim, J.Y. Park, H.J. Lee, H.R. Moon, and H.Y. Chung Biochimie 94 2012 533 540
35. H. Tada, O. Shiho, K. Kuroshima, M. Koyama, and K. Tsukamoto J. Immunol. Methods 93 1986 157 165