New saccharin derivatives as tyrosinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 9, 2012, Pages 2811-2821

  Gener, Nahit ^a   Demir, Dudu ^a   Sonmez, Fatih ^b   Kucukislamoglu, Mustafa ^b  

^a BALIKESIR UNIVERSITY   (Turkey)

^b SAKARYA UNIVERSITY   (Turkey)

Author keywords

Saccharin; Thiourea; Tyrosinase inhibitors; Urea

Indexed keywords

2 METHYL 5 NITROBENZENESULFONAMIDE; 2 METHYL 5 NITROBENZENESULFONYLCHLORIDE; 6 (2 FLUOROPHENYLTIOURENYL) SACCHARIN; 6 (2 FLUOROPHENYLURENYL) SACCHARIN; 6 (2,4 DICHLOROPHENYLTHIOURENYL) SACCHARIN; 6 (3 CHLOROPHENYLTHIOURENYL) SACCHARIN; 6 (3 CHLOROPHENYLURENYL) SACCHARIN; 6 (3 FLUOROPHENYLTIOURENYL) SACCHARIN; 6 (3 FLUOROPHENYLURENYL) SACCHARIN; 6 (3 IODOPHENYLTHIOURENYL) SACCHARIN; 6 (3 METHOXYPHENYLURENYL) SACCHARIN; 6 (3 NITROPHENYLURENYL) SACCHARIN; 6 (3,4 DICHLOROPHENYLURENYL) SACCHARIN; 6 (3,5 DICHLOROPHENYLTHIOURENYL) SACCHARIN; 6 (4 CHLOROPHENYLURENYL) SACCHARIN; 6 (4 FLUOROPHENYLTIOURENYL) SACCHARIN; 6 (4 FLUOROPHENYLURENYL) SACCHARIN; 6 (4 METHOXYPHENYLTHIOURENYL) SACCHARIN; 6 (4 METHOXYPHENYLURENYL) SACCHARIN; 6 (4 METHYLPHENYLTHIOURENYL) SACCHARIN; 6 (4 METHYLPHENYLURENYL) SACCHARIN; 6 (4 NITROPHENYLTHIOURENYL) SACCHARIN; 6 (4 NITROPHENYLURENYL) SACCHARIN; 6 (PHENYLTHIOURENYL) SACCHARIN; 6 (PHENYLURENYL) SACCHARIN; 6 AMINOSACCHARIN; 6 NITROSACCHARIN; SACCHARIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

ENZYME ACTIVATION; ENZYME INHIBITORS; KINETICS; MONOPHENOL MONOOXYGENASE; MUSA; QUANTUM THEORY; SACCHARIN; SOFTWARE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84859891724     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.03.033     Document Type: Article

References (51)

1. K.S. Yeung, N.A. Meanwell, Y. Li, and Q. Gao Tetrahedron Lett. 39 1998 1483
2. M.E. Gerland, T. Sakata, M.J. Fisher, T. Masui, and M.S. Cohen Cancer Res. 49 1989 225
3. D.C. Martyn, M.J.B. Moore, and A.D. Abell Curr. Pharm. Des. 5 1999 405
4. W.C. Groutas, J.B. Epp, R. Venkataraman, R. Kuang, T.M. Truong, J.J. McClenahan, and O. Prakash Bioorg. Med. Chem. Lett. 4 1996 1393
5. M.A. Patane, R.M. Dipardo, R.P. Price, R.S.L. Chang, R.W. Ransom, S.S. O'Malley, J. Di Salvo, and M.G. Bock Bioorg. Med. Chem. Lett. 8 1998 2495
6. K.D. Combrink, H.B. Gulgeze, N.A. Meanwell, B.C. Pearce, P. Zulan, G.S. Bisacchi, D.G.M. Roberts, P. Stanley, and S.M. Seiler J. Med. Chem. 41 1998 4854
7. G. Gonzalez-Martin, C. Lyndon, and C. Sunkel Eur. J. Pharm. Biopharm. 46 1998 293
8. G. Caliendo, F. Fiorino, E. Perissutti, B. Severino, D. Scolaro, S. Gessi, E. Cattabriga, P.A. Borea, and V. Santagada Eur. J. Pharm. Sci. 16 2002 15
9. H.T. Nagasawa, S.P. Kawle, J.A. Elberling, E.G. DeMaster, and J.M. Fukuto J. Med. Chem. 1995 1865 38
10. C.E. Sunkel, M.F. de Casa-Junna, F.J. Cillero, J.G. Piego, and M.P. Ortega J. Med. Chem. 1988 1886 31
11. A.S. Gaballa, S.M. Teleb, and T. Muller Spectrochim. Acta Part A 70 2008 1187
12. O.Z. Yesilel, C. Darcan, and E. Sahin Polyhedron 27 2008 905
13. F. Clerici, M.L. Gelmi, S. Pellegrino, and D. Pocar Top. Heterocycl. Chem. 9 2007 179
14. S. Majumdar, J. Juntunen, S. Sivendran, N. Bharti, and K.B. Sloan Tetrahedron Lett. 47 2006 8981
15. P.M. Bhatt, N.V. Ravindra, R. Banerjee, and G.R. Desiraju Chem. Commun. 1078 2005
16. S. Basavoju, D. Boström, and S.P. Velaga Pharm. Res. 25 2008 530
17. J.G. Lombardino, E.H. Wiseman, and W. Mclamore J. Med. Chem. 14 1971 1171
18. K.M. Khan, S. Saeed, M. Ali, M. Gohar, J. Zahid, A. Khan, S. Perveen, and M.I. Choudhary Bioorg. Med. Chem. 17 2009 2447
19. S. Galiano, J. Ceras, N. Cirauqui, S. Perez, L. Juanenea, G. Rivera, I. Aldana, and A. Monge Bioorg. Med. Chem. 15 2007 3896
20. R.K. Thalji, N. Aiyar, E.A. Davenport, J.A. Erhardt, L.A. Kallal, D.M. Morrow, S. Senadhi, C.L. Burns-Kurtis, and J.P. Marino Jr Bioorg. Med. Chem. 20 2010 4104
21. W. Pan, H.O. Miao, Y.J. Xu, E.C. Navarro, J.R. Tonra, E. Corcoran, A. Lahiji, P. Kussie, A.S. Kiselyov, W.C. Wong, and H. Liu Bioorg. Med. Chem. Lett. 16 2006 409
22. H. Dulude, R. Salvador, and G. Gallant Bioorg. Med. Chem. 3 1995 151
23. M. Simunovic, I. Perkovic, B. Zorc, K. Ester, M. Kralj, D. Hadjipavlou-Litina, and E. Pontiki Bioorg. Med. Chem. 17 2009 5605
24. H. Ogita, Y. Isobe, H. Takaku, R. Sekine, Y. Goto, S. Misawa, and H. Hayashi Bioorg. Med. Chem. 2002 1865 10
25. C.T. Supuran, A. Scozzafava, B.C. Jurca, and M.A. Ilies Eur. J. Med. Chem. 33 1998 83
26. K.K. Song, H. Huang, P. Han, C.L. Zhang, Y. Shi, and Q.X. Chen Biochem. Biophys. Res. Commun. 342 2006 1147
27. Q.X. Chen, X.D. Liu, and H. Huang Biochemistry (Moscow) 68 2003 644
28. I. Kubo, K.I. Nihei, and K. Shimizu Bioorg. Med. Chem. Lett. 12 2004 5343
29. R. Matsuura, H. Ukeda, and M. Sawamura J. Agric. Food. Chem. 54 2006 2309
30. W. Yi, and R. Cao Eur. J. Med. Chem. 45 2010 639
31. A.K. Gupta, M.D. Gover, K.N. Nouri, and S. Taylor J. Am. Acad. Dermatol. 55 2006 1048
32. P. Thanigaimalai, and T.A.L. Hoang Bioorg. Med. Chem. Lett. 20 2010 2991
33. Y.J. Zhu, H.T. Zhou, and Y.H. Hu Food Chem. 124 2011 298
34. M. Ashida, and P. Brey Proc. Natl. Acad. Sci. U.S.A. 92 1995 10698
35. G. Battaini, E. Monzani, L. Casella, L. Santagostini, and R. Pagliarin J. Biol. Inorg. Chem. 5 2000 262
36. H. Kamogawa, S. Yamamoto, and M. Nanasawa Bull. Chem. Soc. Jpn. 55 1982 3824
37. N. Wuyts, D.De. Waele, and R. Swennen Plant Phys. Biochem. 44 2006 308 314
38. F.C. Richard-Forget, P.M. Groupy, and J.J. Nicholas J. Agric. Food Chem. 40 1992 2108 2113
39. L.A. Sayaverde-Soto, and M.W. Montgomery J. Food Sci. 51 1986 1531 1535
40. J.R. Whitaker, and C.Y. Lee Recent Advances in Chemistry of Enzymatic Browning: An Overview Y.L. Chang, J.R. Whitaker, Enzymatic Browning and its Prevention 1995 ACS Symposium Series 600, American Chemical Society Washington DC 2 7
41. J.R. Whitaker Enzyme Inhibitors J.R. Whitaker, Principles of Enzymology for the Food Sciences second ed. 1994 Marcel Dekker Inc. New York 241 270
42. T. Aydemir Inter. J. Food Properties 13 2010 475 485
43. J.J. Nicholas, F.C. Richard-Forget, P.M. Goupy, M.J. Amiot, and S.Y. Aubert CRC Crit. Rev. Food Sci. Nut. 34 1994 109 157
44. D.H. Halim, and M.W. Montgomery J. Sci. 43 1978 603 610
45. V. Kahn J. Sci. 50 1985 111 115
46. Gaussian 09, Revision A.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A. Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.; Gaussian, Inc.; Wallingford CT, 2009.
47. GaussView, Version 5, Dennington, R.; Keith, T.; Millam, J.; Semichem. Inc., Shawnee Mission KS, 2009.
48. S. Ohno, N. Matsumoto, M. Watanabe, and S. Nakajin J. Steroid Biochem. Mol. Biol. 88 2004 175
49. P. Wesche-Ebeling, and M.W. Montgomery J. Food Sci. 55 1990 1320
50. O. Arslan, M. Erzengin, S. Sinan, and O. Ozensoy Food Chem. 88 2004 479
51. J.C. Espin, M. Morales, R. Varon, J. Tudela, and F. Garcia-Canovas Anal. Biochem. 43 1995 2807