Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 4330-4335

  Yi, Wei ^a,d   Dubois, Carole ^b   Yahiaoui, Samir ^a   Haudecoeur, Romain ^a   Belle, Catherine ^c   Song, Huacan ^d   Hardré, Renaud ^b   Réglier, Marius ^b   Boumendjel, Ahcne ^a  

^a Université Joseph Fourier   (France)

^b AIX MARSEILLE UNIVERSITÉ   (France)

^c Centre National de la Recherche Scientifique   (France)

^d SUN YAT SEN UNIVERSITY   (China)

Author keywords

Arylthiosemicarbazones; Melanin; Pigmentation; Tyrosinase inhibitors

Indexed keywords

1 (2 PHENYLETHYLIDENE)THIOSEMICARBAZONE; 1 (3 PHENYLPROPYLIDENE)THIOSEMICARBAZONE; 1 (FURAN 2 YLMETHYLENE)THIOSEMICARBAZONE; 1 (NAPHTHALEN 1 YLMETHYLENE)THIOSEMICARBAZONE; 1 (NAPHTHALEN 2 YLMETHYLENE)THIOSEMICARBAZONE; 1 (PYRIDIN 2 YLMETHYLENE)THIOSEMICARBAZONE; 1 (QUINOLIN 2 YLMETHYLENE)THIOSEMICARBAZONE; 1 [(1 METHYL 1H INDOL 3 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1 METHYL INDOL 2 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1 METHYL INDOL 3 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1 METHYL INDOL 5 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1H INDOL 2 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1H INDOL 3 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1H INDOL 5 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(1H PYRROL 2 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(2 FLUOROPHENYL)METHYLENE]THIOSEMICARBAZONE; 1 [(3 FLUOROPHENYL)METHYLENE]THIOSEMICARBAZONE; 1 [(4 FLUOROPHENYL)METHYLENE]THIOSEMICARBAZONE; 1 [(5 HYDROXY 4 OXO 4H PYRAN 2 YL)METHYLENE]THIOSEMICARBAZONE; 1 [(5 METHOXY 4 OXO 4H PYRAN 2 YL)METHYLENE]THIOSEMICARBAZONE; 1 BENZYLIDENETHIOSEMICARBAZONE; ARYLTHIOSEMICARBAZONE; DERMATOLOGICAL AGENT; KOJIC ACID; MONOPHENOL MONOOXYGENASE; OXYGENASE INHIBITOR; TYROSINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEMETHYLATION; DEPIGMENTATION; DRUG SYNTHESIS; ENZYME INHIBITION; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE;

AGARICALES; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MELANINS; MONOPHENOL MONOOXYGENASE; SKIN PIGMENTATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THIOSEMICARBAZONES;

EID: 80052928807     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.07.003     Document Type: Article

References (33)

1. C.E. Griffiths, L.J. Finkel, C.M. Ditre, T.A. Hamilton, C.N. Ellis, and J. Voorhees Br. J. Dermatol. 129 1993 415 421
2. A.J. Kanwar, S. Dhar, and S. Kaur Dermatology 188 1994 170
3. M. Perez-Gilabert, and F. Garcia-Carmona Biochem. Biophys. Res. Commun. 285 2001 257 261
4. A.J.M. Schoot-Uiterkamp, and H.S. Mason Proc. Natl. Acad. Sci. U.S.A. 70 1973 993 996
5. C.W.G. Van Gelder, W.H. Flurkey, and H.J. Wichers Phytochemistry 45 1997 1309 1323
6. N.H. Shin, S.Y. Ryu, E.J. Choi, S.H. Kang, I.M. Chang, K. Min, and Y. Kim Biochem. Biophys. Res. Commun. 243 1998 801 803
7. A.M. Kligman, and I. Willis Arch. Dermatol. 111 1975 40 48
8. F. Alena, K. Jimbow, and S. Ito Cancer Res. 50 1990 3743 3747
9. K. Tasaka, C. Kamei, S. Nakano, Y. Takeuchi, and M. Yamato Meth. Find. Exp. Clin. Pharmacol. 20 1998 99 109
10. Y.-J. Kim, and H. Uyama Cell. Mol. Life Sci. 62 2005 1707 1723
11. M.S. Eller, K. Ostrom, and B.A. Glichrest Proc. Natl. Acad. Sci. U.S.A. 93 1996 1087 1092
12. S.-Y. Seo, V.K. Sharma, and N. Sharma J. Agric. Food Chem. 51 2003 2837 2858
13. J. Daniel, US Patent 2006135618 (2006).
14. M. Criton, and V.L. Mellay-Hamon Bioorg. Med. Chem. Lett. 18 2008 3607 3610
15. Z.C. Li, L.H. Chen, X.J. Yu, Y.H. Hu, K.K. Song, X.W. Zhou, and Q.X. Chen J. Agric. Food Chem. 58 2010 12537 12540
16. Y.J. Zhu, K.K. Song, Z.C. Li, Z.Z. Pan, Y.J. Guo, J.J. Zhou, Q. Wang, B. Liu, and Q.X. Chen J. Agric. Food Chem. 57 2009 5518 5523
17. C.-B. Xue, L. Wang, W.-C. Luo, X.-Y. Xie, L. Jiang, and T. Xiao Bioorg. Med. Chem. 15 2007 2006 2015
18. J.B. Liu, W. Yi, Y.Q. Wan, L. Ma, and H.C. Song Bioorg. Med. Chem. 14 2008 1096 1102
19. W. Yi, R.H. Cao, H. Wen, Q. Yan, B.H. Zhou, L. Ma, and H.C. Song Bioorg. Med. Chem. Lett. 19 2009 6157 6160
20. J.B. Liu, R.H. Cao, W. Yi, C.M. Ma, Y.Q. Wan, B.H. Zhou, L. Ma, and H.C. Song Eur. J. Med. Chem. 44 2009 1773 1778
21. W. Yi, R.H. Cao, Z.Y. Chen, L. Yu, L. Ma, and H.C. Song Chem. Pharm. Bull. 571 2009 1273 1277
22. W. Yi, R.H. Cao, Z.Y. Chen, L. Yu, H. Wen, Q. Yan, L. Ma, and H.C. Song Chem. Pharm. Bull. 58 2010 752 754
23. K.C. Lee, P. Thanigaimalai, V.K. Sharma, M.S. Kim, E. Roh, B.Y. Hwang, Y. Kim, and S.H. Jung Bioorg. Med. Chem. Lett. 20 2010 6794 6796
24. P. Thanigaimalai, T.A.L. Hoang, K.C. Lee, S.C. Bang, V.K. Sharma, C.Y. Yun, E. Roh, B.Y. Hwang, Y. Kim, and S.H. Jung Bioorg. Med. Chem. Lett. 20 2010 2991 2993
25. T. Klabunde, C. Eicken, J.C. Sacchettini, and B. Krebs Nat. Struct. Biol. 5 1998 1084 1090
26. C. Gerdemann, C. Eicken, and B. Krebs Acc. Chem. Res. 35 2002 183 191
27. S. Okombi, D. Rival, S. Bonnet, A.M. Mariotte, E. Perrier, and A. Boumendjel J. Med. Chem. 49 2006 329 333
28. S. Okombi, D. Rival, S. Bonnet, A.M. Mariotte, E. Perrier, and A. Boumendjel Bioorg. Med. Chem. Lett. 16 2006 2252 2255
29. T.-S. Chang Int. J. Mol. Sci. 10 2009 2440 2475
30. M.M. O'Malley, F. Damkaci, and T.R. Kelly Org. Lett. 8 2006 2651 2652
31. H.D. Becker Acta Chem. Scand. 16 1962 78 82
32. G. Battaini, E. Monzani, L. Casella, L. Santagostini, and R. Pagliarin J. Biol. Inorg. Chem. 5 2000 262 268
33. S. Yamazaki, and S. Itoh J. Am. Chem. Soc. 125 2003 13034 13035