Synthesis and Evaluation of 2(3H)-Thiazole Thiones as Tyrosinase Inhibitors

Archiv der Pharmazie

Volumn 345, Issue 8, 2012, Pages 629-637

  Emami, Saeed ^a   Hosseinimehr, Seyed Jalal ^a   Shahrbandi, Kami ^a   Enayati, Ahmad Ali ^b   Esmaeeli, Zahra ^a  

^a MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

ADME Tox screening; Phenolic antioxidants; Radical scavenging activity; Thiazole; Thiazoline; Tyrosinase inhibitors

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 1,3,4 OXADIAZOLE 2(3H)THIONE; 3 METHYL 4 PHENYLTHIAZOLE 2(3H)THIONE; 3,4 DIHYDROQUINAZOLINE 2(1H)THIONE; 3,4 DIPHENYLTHIAZOLE 2(3H)THIONE; 4 (4 HYDROXY 3 METHOXYPHENYL)3 METHYLTHIAZOLE 2(3H)THIONE; 4 (4 HYDROXYPHENYL) 3 METHYLTHIAZOLE 2(3H)THIONE; 4 (4 HYDROXYPHENYL) 3 PHENYLTHIAZOLE 2(3H)THIONE; 4 HYDROXY 3 METHYL 4 PHENYLTHIAZOLIDINE 2 THIONE; 4 HYDROXY 4 (4 HYDROXY 3 METHOXYPHENYL) 3 METHYLTHIAZOLIDINE 2 THIONE; 4 HYDROXY 4 (4 HYDROXYPHENYL) 3 METHYLTHIAZOLIDINE 2 THIONE; ENZYME INHIBITOR; EUGENOL; FERULIC ACID; IMIDAZOLIDINE 2 THIONE; KOJIC ACID; PARA COUMARIC ACID; PHENOL; TETRAHYDROPYRIMIDINE 2 (1H)THIONE; THIAZOLE DERIVATIVE; TYROSINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER MODEL; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; EVALUATION; IC 50; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TOXICITY TESTING;

DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; FREE RADICAL SCAVENGERS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; THIONES;

EID: 84864580574     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201200028     Document Type: Article

References (32)

1. J. R. Whitaker, Polyphenol oxidase. In: Food Enzymes, Structure and Mechanism (Ed.:, D. W. S. Wong,), Chapman & Hall, New York 1995, pp. 271-307.
2. I. Kubo, I. Kinst-Hori, S. K. Chaudhuri, Y. Kubo, Y. Sánchez, T. Ogura, Bioorg. Med. Chem. 2000, 8, 1749-1755.
3. M. Perez-Gilabert, F. Garcia-Carmona, Biochem. Biophys. Res. Commun. 2001, 285, 257-261.
4. P. Grimes, J. J. Nordlund, A. G. Pandya, S. Taylor, M. P. Rendon, P. Ortonne, J. Am. Acad. Dermatol. 2006, 54, S255-S256.
5. A. G. Pandya, I. L. Guevara, Dermatol. Clin. 2000, 18, 91-98.
6. D. T. Hartong, E. L. Berson, T. P. Dryja, Lancet 2006, 368, 1795-1809.
7. A. M. Mayer, Phytochemistry 1987, 26, 11-20.
8. S. Passi, M. Nazzaro-Porro, Br. J. Dermatol. 1981, 104, 659-665.
9. S. Briganti, E. Camera, M. Picardo, Pigm. Cell. Res. 2003, 16, 101-110.
10. K. I. Nihei, I. Kubo, Bioorg. Med. Chem. Lett. 2003, 13, 2409-2412.
11. S. Y. Seo, V. K. Sharma, N. Sharma, J. Agric. Food Chem. 2003, 51, 2837-2853.
12. C. Gõmez-Cordovés, B. Bartolomé, W. Vieira, V. M. Virador, J. Agric. Food Chem. 2001, 49, 1620-1624.
13. E. T. Arung, E. Matsubara, I. W. Kusuma, E. Sukaton, K. Shimizu, R. Kondo, Fitoterapia 2011, 82, 198-202.
14. K. W. Lam, A. Syahida, Z. Ul-Haq, M. B. Abdul Rahman, N. H. Lajis, Bioorg. Med. Chem. Lett. 2010, 20, 3755-3759.
15. P. Thanigaimalai, K.-C. Lee, S.-C. Bang, J.-H. Lee, C.-Y. Yun, E. Roh, B.-Y. Hwang, Y. Kim, S.-H. Jung, Bioorg. Med. Chem. 2010, 18, 1135-1142.
16. P. Thanigaimalai, V. K. Sharma, K.-C. Lee, C.-Y. Yun, Y. Kim, S.-H. Jung, Bioorg. Med. Chem. Lett. 2010, 20, 4771-4773.
17. P. Thanigaimalai, K.-C. Lee, S.-C. Bang, J.-H. Lee, C.-Y. Yun, E. Roh, B.-Y. Hwang, Y. Kim, S.-H. Jung, Bioorg. Med. Chem. 2010, 18, 1555-1562.
18. S. Emami, A. Foroumadi, M. Falahati, E. Lotfali, S. Rajabalian, S.-A. Ebrahimi, S. Farahyar, A. Shafiee, Bioorg. Med. Chem. Lett. 2008, 18, 141-146.
19. S. Emami, A. Foroumadi, Chin. J. Chem. 2006, 24, 791-794.
20. V. J. Hearing, Methods in Enzymology, Vol. 142, Academic Press, New York 1987, p. 154.
21. T.-S. Chang, H.-Y. Ding, H.-C. Lin, Biosci. Biotechnol. Biochem. 2005, 69, 1999-2001.
22. T. Hatano, H. Kagawa, T. Yasuhara, T. Okuda, Chem. Pharm. Bull. 1988, 36, 2090-2097.
23. G. Battaini, E. Monzani, L. Casella, L. Santagostini, R. Pagliarin, J. Biol. Inorg. Chem. 2000, 5, 262-268.
24. L. P. Xie, Q. X. Chen, H. Huang, H. Z. Wang, R. Q. Zhang, Biochemistry (Moscow) 2003, 68, 487-491.
25. T. Klabunde, C. Eicken, J. C. Sacchettini, B. Krebs, Nat. Struct. Biol. 1998, 5, 1084-1090.
26. J. Liu, F. Wu, L. Chen, J. Hu, L. Zhao, C. Chen, L. Peng, Bioorg. Med. Chem. Lett. 2011, 21, 2376-2379.
27. A. de la Nuez, R. Rodríguez, Biotecnol. Aplicada 2008, 25, 97-110.
28. C. A. Lipinski, Drug Discovery Today: Technol. 2004, 1, 337-341.
29. D. C. Young, Computational Drug Design, John Wiley & Sons Inc, Hoboken, New Jersey 2009.
30. T. Piamphongsant, Int. J. Dermatol. 1998, 37, 897-903.
31. C. I. Wei, T. S. Huang, S. Y. Fernando, K. T. Chung, Toxicol. Lett. 1991, 59, 213-220.
32. X.-H. Gao, L. Zhang, H. Wei, H.-D. Chen, Clin. Dermatol. 2008, 26, 367-374.